新型联芳共轭有机化合物的合成及其性能研究
|
摘要
联芳类化合物因其具有特殊的光学和电化学性能,应用非常广泛,如可用于液晶材料、有机功能材料、医药、农药和有机合成中间体等领域。一些含有特殊官能团(如巯基、硝基等)的联芳类化合物因为具有特殊的光电性能,受到了广大科学家的广泛关注。比如含硝基的化合物经过进一步反应可生成具有良好光电性能的咔唑或多聚咔唑;含巯基的化合物可在金、银等金属表面形成自组装单分子膜,而以共轭有机薄膜为基础的电子器件可应用于有机电致发光器件、有机负电阻器件、分子电路器件及超微型芯片、超高密度信息纪录技术等方面。目前,合成联芳类化合物的主要方法就是偶联反应。
结合该领域的研究现状,本论文主要研究了以下内容:采用钯催化的Suzuki偶联反应和Sonagashira偶联反应,共合成了3个系列39个未见文献报道的结构新颖的联芳类化合物,通过核磁、红外、元素分析和高分辨质谱等测试手段对所合成的新化合物进行了结构表征,测试了所合成化合物的紫外光谱、荧光光谱,讨论了结构与性能间的关系。用热重分析测试了热稳定性,循环伏安法测试了部分化合物的电化学行为,高斯软件计算了化合物的最优分子构型、最高占有轨道(HOMO)以及最低空轨道(LUMO)的能级。
在Pd(PPh_3)_4催化剂存在下,4-溴-1-碘-2-硝基苯与对硫甲基苯硼酸反应,区域选择性地合成了4′-溴-2′-硝基-4-硫甲基联苯(3),收率高达87%。化合物3进一步与不同芳基硼酸进行Suzuki偶联反应合成了17个含硝基和硫甲基的不对称联芳类化合物(4a-q)。紫外光谱结果表明,化合物4a-q的最大紫外吸收波长范围是241～318 nm。化合物4″-甲酰基-4-硫甲基-2′-硝基-1,1′,4′,1″-三联苯(4j)较其它不对称的三联苯化合物具有较大的紫外吸收波长299 nm。含杂环的化合物2-(4′-硫甲基)-2-硝基联苯-4-)苯并噻吩(4p)具有最大的紫外的吸收波长(318 nm)。热重分析结果表明,这一系列化合物具有较好的热稳定性,失重5%时的温度都在200℃以上。循环伏安测试结果表明,该系列化合物的氧化部分均不可逆,还原部分出现两个明显的还原峰,-1.22 V处的还原峰是可逆的。
以Pd(PPh_3)_4为催化剂,碳酸钾为缚酸剂的条件下,1,4-对苯二硼酸频哪醇酯与取代的4-溴-2-硝基联苯(6a-d)进行双Suzuki偶联反应,一步合成了对称的含硝基五联苯类化合物(7a-d),收率为44～75%。类似地,2,5-二硼酸频哪醇酯噻吩与取代的4-溴-2-硝基联苯(6a-d)也可以进行双Suzuki偶联反应,反应在Pd(PPh_3)_4为催化剂,氟化铯为缚酸剂,1,4-二氧六环为溶剂的条件下,生成的对称含硝基的噻吩/苯共聚物(9a-d)的收率为30～80%。紫外光谱结果表明,取代的五联苯类化合物(7a-d)的最大紫外吸收波长范围是295～307 nm,其最大吸收波长与苯环上的取代基性质有关,供电子基团使其最大紫外吸收波长红移,其最大紫外吸收波长的顺序为H(7a)＜Et(7b)＜OMe(7c)＜SMe(7d);含硝基的噻吩/苯共聚物(9a-d)的最大紫外吸收波长范围是343～348 nm,同样,供电子基团使其最大紫外吸收波长红移,其最大紫外吸收波长的顺序为H(9a)＜Et(9b)＜OMe(9c)≈SMe(9d)。化合物7a-d同9a-d的最大紫外吸收波长相比发现:化合物9a-d的最大紫外吸收波长发生较大红移。热重分析结果表明,取代的五联苯类化合物(7a-d)和噻吩/苯共聚物(9a-d)都具有良好的热稳定性,失重5%时的温度都大于200℃。循环伏安测试结果可知,化合物7a-d和化合物9a-d的氧化部分不可逆,还原部分在-1.22 V处的还原峰是可逆的。
采用汇聚式的合成方法即Suzuki偶联反应结合Sonogashira偶联反应合成了14个新型的寡聚苯乙炔撑(oligo(phenylene-ethynylene)s,OPEs)衍生物。首先,Pd(PPh_3)_4作催化剂,K_2CO_3作碱,DME作溶剂的条件下,4-溴-2-硝基苯乙炔基三甲基硅烷(10)与不同取代苯硼酸进行Suzuki偶联反应生成化合物11a-m,然后脱保护生成相应的含硝基联苯乙炔化合物(12a-m)。其次,以Pd_2(dba)_3作催化剂,CuI作共催化剂,PPh_3作配体,(i-Pr)_2NEt作碱的条件下,对硫乙酰基碘苯(13)与不同取代的化合物(12a-m)反应生成OPEs衍生物14a～m。化合物17的合成与此相似。紫外光谱结果表明,化合物14a～m和17的最大紫外吸收波长范围是304～321 nm。一般来说,引入的取代基团无论是吸电子基团还是供电子基团,最大紫外吸收波长发生明显红移现象(只有一个例外,14a蓝移)。化合物S-4-(4′-硫甲基-3-硝基联苯-4-乙炔基)苯硫乙酰酯(14m)具有最大的紫外吸收波长321nm。热重分析结果表明,OPEs衍生物都具有非常好的热稳定性,失重5%时的温度都在200℃以上。循环伏安测试结果表明,OPEs衍生物的氧化部分不可逆,还原部分在-1.1 V左右的峰是可逆的。
Currently,polyaryls are materials of considerable interest for chemists,physicists, and material scientists,which are found at the core of a wide variety of interesting organic molecules,ranging from pharmaceutical agents,liquid-crystalline molecules, pesticides,dyes,nano-matefials to OLED materials.Polyaryls,which contained functional groups such as nitro group and thiol group,have been the focus of intense research because of their interesting optical and electrical properties.For instance, polyaryls containing nitro group could be transformed to polyindolocarbazole and polydiindolocarbazole,which showed good optical and electrochemical properties. Polyaryls containing thiol group can form self-assembled monolayers(SAMs) on the surface of Au,Ag or other metals.SAMs plays an important role in the construct ordered nanostructure in molecular electronics.Substituting conjugated organic thin-film-based electronic devices can be used in light-emitting devices,organic negative resistance devices,molecular circuit components and ultra-micro-chip, ultra-high density information records technology,and so on.Now,the main synthetic methods of polyaryls were cross-coupling reaction.
Thirty-nine novel polyarylenes were synthesized using Suzuki cross-coupling reaction and Sonogashira cross-coupling reaction catalyzed by palladium.Their structures were characterized by IR,NMR,EA and HRMS.The ultraviolet absorption spectra and fluorescence spectra were investigated and the relationship between molecular structure and spectra properties were studied.The thermal properties were tested by thermo-gravimetric analysis(TGA) and the electrochemical properties were investigated by cyclic voltammetry(CV).The geometric molecular structures were calculated by the software of Gaussian 03 and the corresponding HOMO and LUMO energies were optimized using the density functional theory(DFT) with correlation functional(B3LYP) and the 3-21G basis set.
Seventeen novel unsymmetrical terphenyls with nitro group and methylthio group were prepared in good yields by regio-selective double Suzuki cross-coupling reaction which employed Pd(PPh_3)_4 as catalyzer,K_2CO_3 as base and 1,2-dimethoxyethane (DME) as solvent.4-Bromo-1-iodo-2-nitrobenzene react with 4-(methylthio)phenylboronic acid to give single cross-coupling product of (4'-bromo-2'-nitrobiphenyl-4-yl)(methyl) sulfane(3) in high yields,which then reacted with various boronic acids to give unsymmetrical terphenyls of(4a-q).The ultraviolet absorption and fluorescence properties of these compounds were recorded in CHCl_3.It was found that UV-vis maximal absorption spectra were in the range of 241～318 nm.Theλ_(abs)~(max) of 4"-formyl-4-methylthio-2'-nitro- 1,1 ',4',1"-terphenyl(4j) was 299 nm and gave a larger red shift than other unsymmetrical terphenyls. Introducing heterocycles(such as thiophene,benzothiophene) showed a large red-shifted absorption compared with unsymmetrical terphenyls.The largest red shift (λ_(abs)~(max) = 318 nm) occurred when benzothiophene is introduced to the compounds. These compounds showed good thermal stabilities(＞200℃) as determined by thermo-gravimetric analysis(TGA).From the figure of cyclic voltarnmetry(CV) we can see that the compounds show two obvious reduction curve and the first reduction curve(reduction potential is -1.22 V) is quasi-reversible.
Four novel functional symmetrical oligophenylenes(7a-d) are prepared by Pd(PPh_3)_4 catalyzed double Suzuki cross-coupling reaction from 1,4-bis(4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene and substituted 4-bromo-2-nitrobiphenyls(6a-d) in DME with K_2CO_3 as base in 44-75%yields. Four novel functional symmetrical oligoarylenes bearing heteroaryl group(9a-d) are prepared by Pd(PPh_3)_4 catalyzed double Suzuki cross-coupling reaction from 2, 5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene and substituted 4-bromo-2-nitrobiphenyls in 1,4-dioxane with Caesium fluoride(CsF) as base in 30-80%yields.Substituted groups had a great effect on spectral properties.It was found that UV-vis maximal absorption spectra of 7a-d were in the range of 295～307 nm.Introducing electron donating group caused bathochromic shift of the absorption maximum and the sequence were H(7a)＜Et(7b)＜OMe(7c)＜SMe(7d).The UV-vis maximal absorption spectra of 9a-d were in the range of 343～348 nm.Introducing electron donating group also caused bathochromic shift of the absorption maximum and the sequence were H(ga)＜Et(9b)＜OMe(9c)≈SMe(9d).Introducing heterocycles caused bathochromie shift compared maximal absorption spectra of 7a-d with 9a-d. These compounds show good thermal stabilities as determined by TGA and the temperature of losing 5%weight is above 200℃.Cyclic voltammetry(CV) of the synthesized compounds show two obvious reduction curve and the first reduction curve(reduction potential is -1.22 V) is quasi-reversible.
Fourteen novel OPEs derivatives are prepared by convergent synthetic methodologies that are based on Suzuki and Sonogashira cross-coupling reaction for aryl-aryl and aryl-ethynyl bond formations.Firstly, ((4-bromo-2-nitrophenyl)ethynyl)trimethylsilane(10) reacted with substituted phenylboronic acid to furnish compounds 11a-m.Reactions was carried out using tetrakis(triphenylphosphine) palladium(0) as catalyst and potassium carbonate(K_2CO_3) as base in 1,2-dimethoxyethane(DME) and H_2O at reflux temperature.Then compounds 11a-m were desilylated using tetrabutylammonium fluoride(TBAF) to furnish the terminal alkynes 12a-m.Secondly,OPEs derivatives 14a-m can readily be achieved by reaction of the corresponding terminal alkynes 12a-m with S-4-iodophenyl ethanethioate(13) using palladium catalyzed Sonogashira cross coupling reaction.Reactions was carried out using tris(dibenzylideneacetone)dipalladium(0) as catalyst,copper(Ⅰ) iodide as co-catalyst and triphenyl phosphine as ligand with N,N-diisopropylethylamine as base.The synthetic route of 17 was similar to 14a-m.It was found that UV-vis maximal absorption spectra of 14a-m and 17 were in the range of 304～321 nm.Introducing substituted groups both electron-donating(R= F,CF_3,C1,CN,acetyl,formyl,vinyl) and electron-withdraw groups(R= methoxy,thiomethyl,ethyl,2,5-dimethoxy) caused bathochromic shift except 14a(R=2,3-dimethoxy) which caused hypsochromic shift.It was found that the largest UV-vis maximal absorption wavelength was 321 nm when R was methylthio group.These compounds show good thermal stabilities as determined by TGA and the temperature of losing 5%weight is above 200℃.Cyclic voltammetry(CV) of the synthesized compounds show two obvious reduction curve and the first reduction curve(reduction potential is -1.10 V) is quasi-reversible.
结合该领域的研究现状,本论文主要研究了以下内容:采用钯催化的Suzuki偶联反应和Sonagashira偶联反应,共合成了3个系列39个未见文献报道的结构新颖的联芳类化合物,通过核磁、红外、元素分析和高分辨质谱等测试手段对所合成的新化合物进行了结构表征,测试了所合成化合物的紫外光谱、荧光光谱,讨论了结构与性能间的关系。用热重分析测试了热稳定性,循环伏安法测试了部分化合物的电化学行为,高斯软件计算了化合物的最优分子构型、最高占有轨道(HOMO)以及最低空轨道(LUMO)的能级。
在Pd(PPh_3)_4催化剂存在下,4-溴-1-碘-2-硝基苯与对硫甲基苯硼酸反应,区域选择性地合成了4′-溴-2′-硝基-4-硫甲基联苯(3),收率高达87%。化合物3进一步与不同芳基硼酸进行Suzuki偶联反应合成了17个含硝基和硫甲基的不对称联芳类化合物(4a-q)。紫外光谱结果表明,化合物4a-q的最大紫外吸收波长范围是241～318 nm。化合物4″-甲酰基-4-硫甲基-2′-硝基-1,1′,4′,1″-三联苯(4j)较其它不对称的三联苯化合物具有较大的紫外吸收波长299 nm。含杂环的化合物2-(4′-硫甲基)-2-硝基联苯-4-)苯并噻吩(4p)具有最大的紫外的吸收波长(318 nm)。热重分析结果表明,这一系列化合物具有较好的热稳定性,失重5%时的温度都在200℃以上。循环伏安测试结果表明,该系列化合物的氧化部分均不可逆,还原部分出现两个明显的还原峰,-1.22 V处的还原峰是可逆的。
以Pd(PPh_3)_4为催化剂,碳酸钾为缚酸剂的条件下,1,4-对苯二硼酸频哪醇酯与取代的4-溴-2-硝基联苯(6a-d)进行双Suzuki偶联反应,一步合成了对称的含硝基五联苯类化合物(7a-d),收率为44～75%。类似地,2,5-二硼酸频哪醇酯噻吩与取代的4-溴-2-硝基联苯(6a-d)也可以进行双Suzuki偶联反应,反应在Pd(PPh_3)_4为催化剂,氟化铯为缚酸剂,1,4-二氧六环为溶剂的条件下,生成的对称含硝基的噻吩/苯共聚物(9a-d)的收率为30～80%。紫外光谱结果表明,取代的五联苯类化合物(7a-d)的最大紫外吸收波长范围是295～307 nm,其最大吸收波长与苯环上的取代基性质有关,供电子基团使其最大紫外吸收波长红移,其最大紫外吸收波长的顺序为H(7a)＜Et(7b)＜OMe(7c)＜SMe(7d);含硝基的噻吩/苯共聚物(9a-d)的最大紫外吸收波长范围是343～348 nm,同样,供电子基团使其最大紫外吸收波长红移,其最大紫外吸收波长的顺序为H(9a)＜Et(9b)＜OMe(9c)≈SMe(9d)。化合物7a-d同9a-d的最大紫外吸收波长相比发现:化合物9a-d的最大紫外吸收波长发生较大红移。热重分析结果表明,取代的五联苯类化合物(7a-d)和噻吩/苯共聚物(9a-d)都具有良好的热稳定性,失重5%时的温度都大于200℃。循环伏安测试结果可知,化合物7a-d和化合物9a-d的氧化部分不可逆,还原部分在-1.22 V处的还原峰是可逆的。
采用汇聚式的合成方法即Suzuki偶联反应结合Sonogashira偶联反应合成了14个新型的寡聚苯乙炔撑(oligo(phenylene-ethynylene)s,OPEs)衍生物。首先,Pd(PPh_3)_4作催化剂,K_2CO_3作碱,DME作溶剂的条件下,4-溴-2-硝基苯乙炔基三甲基硅烷(10)与不同取代苯硼酸进行Suzuki偶联反应生成化合物11a-m,然后脱保护生成相应的含硝基联苯乙炔化合物(12a-m)。其次,以Pd_2(dba)_3作催化剂,CuI作共催化剂,PPh_3作配体,(i-Pr)_2NEt作碱的条件下,对硫乙酰基碘苯(13)与不同取代的化合物(12a-m)反应生成OPEs衍生物14a～m。化合物17的合成与此相似。紫外光谱结果表明,化合物14a～m和17的最大紫外吸收波长范围是304～321 nm。一般来说,引入的取代基团无论是吸电子基团还是供电子基团,最大紫外吸收波长发生明显红移现象(只有一个例外,14a蓝移)。化合物S-4-(4′-硫甲基-3-硝基联苯-4-乙炔基)苯硫乙酰酯(14m)具有最大的紫外吸收波长321nm。热重分析结果表明,OPEs衍生物都具有非常好的热稳定性,失重5%时的温度都在200℃以上。循环伏安测试结果表明,OPEs衍生物的氧化部分不可逆,还原部分在-1.1 V左右的峰是可逆的。
Currently,polyaryls are materials of considerable interest for chemists,physicists, and material scientists,which are found at the core of a wide variety of interesting organic molecules,ranging from pharmaceutical agents,liquid-crystalline molecules, pesticides,dyes,nano-matefials to OLED materials.Polyaryls,which contained functional groups such as nitro group and thiol group,have been the focus of intense research because of their interesting optical and electrical properties.For instance, polyaryls containing nitro group could be transformed to polyindolocarbazole and polydiindolocarbazole,which showed good optical and electrochemical properties. Polyaryls containing thiol group can form self-assembled monolayers(SAMs) on the surface of Au,Ag or other metals.SAMs plays an important role in the construct ordered nanostructure in molecular electronics.Substituting conjugated organic thin-film-based electronic devices can be used in light-emitting devices,organic negative resistance devices,molecular circuit components and ultra-micro-chip, ultra-high density information records technology,and so on.Now,the main synthetic methods of polyaryls were cross-coupling reaction.
Thirty-nine novel polyarylenes were synthesized using Suzuki cross-coupling reaction and Sonogashira cross-coupling reaction catalyzed by palladium.Their structures were characterized by IR,NMR,EA and HRMS.The ultraviolet absorption spectra and fluorescence spectra were investigated and the relationship between molecular structure and spectra properties were studied.The thermal properties were tested by thermo-gravimetric analysis(TGA) and the electrochemical properties were investigated by cyclic voltammetry(CV).The geometric molecular structures were calculated by the software of Gaussian 03 and the corresponding HOMO and LUMO energies were optimized using the density functional theory(DFT) with correlation functional(B3LYP) and the 3-21G basis set.
Seventeen novel unsymmetrical terphenyls with nitro group and methylthio group were prepared in good yields by regio-selective double Suzuki cross-coupling reaction which employed Pd(PPh_3)_4 as catalyzer,K_2CO_3 as base and 1,2-dimethoxyethane (DME) as solvent.4-Bromo-1-iodo-2-nitrobenzene react with 4-(methylthio)phenylboronic acid to give single cross-coupling product of (4'-bromo-2'-nitrobiphenyl-4-yl)(methyl) sulfane(3) in high yields,which then reacted with various boronic acids to give unsymmetrical terphenyls of(4a-q).The ultraviolet absorption and fluorescence properties of these compounds were recorded in CHCl_3.It was found that UV-vis maximal absorption spectra were in the range of 241～318 nm.Theλ_(abs)~(max) of 4"-formyl-4-methylthio-2'-nitro- 1,1 ',4',1"-terphenyl(4j) was 299 nm and gave a larger red shift than other unsymmetrical terphenyls. Introducing heterocycles(such as thiophene,benzothiophene) showed a large red-shifted absorption compared with unsymmetrical terphenyls.The largest red shift (λ_(abs)~(max) = 318 nm) occurred when benzothiophene is introduced to the compounds. These compounds showed good thermal stabilities(＞200℃) as determined by thermo-gravimetric analysis(TGA).From the figure of cyclic voltarnmetry(CV) we can see that the compounds show two obvious reduction curve and the first reduction curve(reduction potential is -1.22 V) is quasi-reversible.
Four novel functional symmetrical oligophenylenes(7a-d) are prepared by Pd(PPh_3)_4 catalyzed double Suzuki cross-coupling reaction from 1,4-bis(4,4,5, 5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene and substituted 4-bromo-2-nitrobiphenyls(6a-d) in DME with K_2CO_3 as base in 44-75%yields. Four novel functional symmetrical oligoarylenes bearing heteroaryl group(9a-d) are prepared by Pd(PPh_3)_4 catalyzed double Suzuki cross-coupling reaction from 2, 5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene and substituted 4-bromo-2-nitrobiphenyls in 1,4-dioxane with Caesium fluoride(CsF) as base in 30-80%yields.Substituted groups had a great effect on spectral properties.It was found that UV-vis maximal absorption spectra of 7a-d were in the range of 295～307 nm.Introducing electron donating group caused bathochromic shift of the absorption maximum and the sequence were H(7a)＜Et(7b)＜OMe(7c)＜SMe(7d).The UV-vis maximal absorption spectra of 9a-d were in the range of 343～348 nm.Introducing electron donating group also caused bathochromic shift of the absorption maximum and the sequence were H(ga)＜Et(9b)＜OMe(9c)≈SMe(9d).Introducing heterocycles caused bathochromie shift compared maximal absorption spectra of 7a-d with 9a-d. These compounds show good thermal stabilities as determined by TGA and the temperature of losing 5%weight is above 200℃.Cyclic voltammetry(CV) of the synthesized compounds show two obvious reduction curve and the first reduction curve(reduction potential is -1.22 V) is quasi-reversible.
Fourteen novel OPEs derivatives are prepared by convergent synthetic methodologies that are based on Suzuki and Sonogashira cross-coupling reaction for aryl-aryl and aryl-ethynyl bond formations.Firstly, ((4-bromo-2-nitrophenyl)ethynyl)trimethylsilane(10) reacted with substituted phenylboronic acid to furnish compounds 11a-m.Reactions was carried out using tetrakis(triphenylphosphine) palladium(0) as catalyst and potassium carbonate(K_2CO_3) as base in 1,2-dimethoxyethane(DME) and H_2O at reflux temperature.Then compounds 11a-m were desilylated using tetrabutylammonium fluoride(TBAF) to furnish the terminal alkynes 12a-m.Secondly,OPEs derivatives 14a-m can readily be achieved by reaction of the corresponding terminal alkynes 12a-m with S-4-iodophenyl ethanethioate(13) using palladium catalyzed Sonogashira cross coupling reaction.Reactions was carried out using tris(dibenzylideneacetone)dipalladium(0) as catalyst,copper(Ⅰ) iodide as co-catalyst and triphenyl phosphine as ligand with N,N-diisopropylethylamine as base.The synthetic route of 17 was similar to 14a-m.It was found that UV-vis maximal absorption spectra of 14a-m and 17 were in the range of 304～321 nm.Introducing substituted groups both electron-donating(R= F,CF_3,C1,CN,acetyl,formyl,vinyl) and electron-withdraw groups(R= methoxy,thiomethyl,ethyl,2,5-dimethoxy) caused bathochromic shift except 14a(R=2,3-dimethoxy) which caused hypsochromic shift.It was found that the largest UV-vis maximal absorption wavelength was 321 nm when R was methylthio group.These compounds show good thermal stabilities as determined by TGA and the temperature of losing 5%weight is above 200℃.Cyclic voltammetry(CV) of the synthesized compounds show two obvious reduction curve and the first reduction curve(reduction potential is -1.10 V) is quasi-reversible.
引文
1.Negishi,E.;King,A.O.;Okukado,N."Selective Carbon-Carbon Bond Formation via Transition Metal Catalysis.3.A Highly Selective Synthesis of Unsymmetrical Biaryls and Diarylmethanes by the Nickel- or Palladium-Catalyzed Reaction of Aryl- and Benzylzinc Derivatives with Aryl Halides", J. Org. Chem. 1977,42 (10), 1821.
2. Kosugi, M; Sasazawa, K.; Shimizu, Y.; Migita, T. "Reactions of allyltin compounds. III. Allylation of aromatic halides with allyltributyltin in the presence of tetrakis(triphenylphosphine)palladium(0)", Chem. Lett. 1977, (3), 301.
3. Milstein, D.; Stille, J. K. "A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium",J. Am. Chem. Soc. 1978,100, 3636.
4. Beletskaya, I. P. Cheprakov, A. V. "The Heck Reaction as a Sharpening Stone of Palladium Catalysis", Chem. Rev. 2000,100 (8), 3009.
5. Chinchilla, R.; Najera, C. "The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry." Chem. Rev. 2007,107, 874.
6. Miyaura, N.; Suzuki, A. "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds", Chem. Rev. 1995,95, 2457.
7. Andersch, J.; Tschierske, C. "Synthesis and liquid crystalline properties of novel laterally connected twins", Liq. Cryst. 1996,21 (1), 51.
8. Berry, R. W. H.; Brocklehurst, P.; Burawoy, A. "Electronic spectra of organic molecules and their interpretation", Tetrahedron 1960,10,109.
9. Brocklehurst, P.; Burawoy, A.; Thompson, A. R. "Electronic spectra of organic molecules and their interpretation. VI. Electronic spectra of p-terphenyl and its derivatives", Tetrahedron 1960,10,102.
10. Iguchi, K.; Nozaki, T.; Imamura, A.; Takahashi, S. "The ultraviolet spectra of monohalo-, mononitro-, and monoamino-p-terphenyls", Bull. Chem. Soc. Jpn.1963, 36, 696.
11. Nozaki, T.; Harada, Y. "Synthesis of mononitro-, monoamino-, and monohalo-p-terphenyls, and their solubility and specific gravity", Bull. Chem.Soc. Jpn. 1962,35, 1783.
12. Tavasli, M.; Bettington, S.; Bryce, M. R.; Batsanov, A. S.; Monkman, A. P."Practical Syntheses of N-Hexylcarbazol-2-yl- and -3-yl-boronic Acids, Their Cross-Coupled Products and a Derived Tris-cyclometalated (Pyridin-2-yl)carbazole Iridium(Ⅲ) Complex",Synthesis 2005,10,1619.
13.Krapchetov,D.A.;Ma,H.;Jen,A.K.Y.;Fischer,D.A.;Loo,Y.L."Solvent-Dependent Assembly of Terphenyl- and Quaterphenyldithiol on Gold and Gallium Arsenide",Langmuir 2005,21(13),5887.
14.Boer,B.D.;Meng,H.;Perepichka,D.F.;Zheng,J.;Frank,M.M.;Chabal,Y.J.;Bao,Z."Synthesis and Characterization of Conjugated Mono- and Dithiol Oligomers and Characterization of Their Self-Assembled Monolayers",Langmuir 2003,19,4272.
15.江浪,黄桂芳,李洪祥,李小凡,胡文平,刘云祈,朱道本。“自组装分子电子器件”,化学进展,2005,1,172.
16.Sabatani,E.;Cohen-Boulakia,J.;Bruening,M.;Rubinstein,I."Thioaromatic Monolayers on Gold:A New Family of Self-Assembling Monolayers",Langmuir 1993,9,2974.
17.Himmel,H.J.;Terfort,A.;Woell,C."Fabrication of a Carboxyl-Terminated Organic Surface with Self-Assembly of Functionalized Terphenylthiols:The Importance of Hydrogen Bond Formation",J.Am.Chem.Soc.1998,120(46),12069.
18.Xue,Y.;Datta,S.;Hong,S.;Reifenberger,R.;Henderson,J.I.;Kubiak,C.P."Negative differential resistance in the scanning-tunneling spectroscopy of organic molecules",Phys.Rev.B:Condens.Matter 1999,59(12),R7852.
19.Ishida,T.;Mizutani,W.;Azehara,H.;Sato,F.;Choi,N.;Akiba,U.;Fujihira,M.;Tokumoto,H."Adsorption processes of self-assembled monolayers made from terphenyl thiols",Langmuir 2001,17(24),7459.
20.Scharf,J.;Strehblow,H.H.;Zeysing,B.;Terfort,A."Electrochemical and surface analytical studies of self-assembled monolayers of three aromatic thiols on gold electrodes",J.Solid State Electrochem.2001,5(6),396.
21.Tran,E.;Grave,C.;Whitesides,G.M.;Rampi,M.A."Controlling the electron transfer mechanism in metal-molecules-metal junctions",Electrochim.Acta 2005,50(25-26),4850.
22.Holmlin,R.E.;Ismagilov,R.F.;Haag,R.;Mujica,V.;Ratner,M.A.;Rampi,M.A.;Whitesides,G.M."Correlating electron transport and molecular structure in organic thin films",Angew.Chem.Int.Ed.2001,40(12),2316.
23.Ishida,T.;Mizutani,W.;Choi,N.;Akiba,U.;Fujihira,M.;Tokumoto,H."Structural Effects on Electrical Conduction of Conjugated Molecules Studied by Scanning Tunneling Microscopy",J.Phys.Chem.B 2000,104(49),11680.
24.Hong,S.;Reifenberger,R.;Tian,W.;Datta,S.;Henderson,J.;Kubiak,C.P."Molecular conductance spectroscopy of conjugated,phenyl-based molecules on Au(111):the effect of end groups on molecular conduction",Superlattices Microstruct.2000,28(4),289.
25.Chen,W.;Wang,L.;Huang,C.;Lin,T.T.;Gao,X.Y.;Loh,K.P.;Chen,Z.K.;Wee,A.T.S."Effect of Functional Group(Fluorine) of Aromatic Thiols on Electron Transfer at the Molecule-Metal Interface",J.Am.Chem.Soc.2006,128(3),935.
26.Holmlin,R.E.;Haag,R.;Chabinyc,M.L.;Ismagilov,R.F.;Cohen,A.E.;Terfort,A.;Rampi,M.A.;Whitesides,G.M."Electron Transport through Thin Organic Films in Metal-Insulator-Metal Junctions Based on Self-Assembled Monolayers",J.Am.Chem.Soc.2001,123(21),5075.
27.Cohen,R.;Stokbro,K.;Martin,J.M.L.;Ratner,M.A."Charge Transport in Conjugated Aromatic Molecular Junctions:Molecular Conjugation and Molecule-Electrode Coupling",J.Phys.Chem.C 2007,111(40),14893.
28.Viljas,J.K.;Pauly,F.;Cuevas,J.C."Photoconductance of organic single-molecule contacts",Phys.Rev.B:Condens.Matter 2007,76(3),033403/1.
29.Goto,T.;Degawa,K.;Inokawa,H.;Furukawa,K.;Nakashima,H.;Sumitomo,K.;Aoki,T.;Torimitsu,K."Molecular-mediated single-electron devices operating at room temperature",Jpn.J.Appl.Phys.2006,45(5A),4285.
30.Maiti,S.K."Quantum transport through organic molecules",Chem.Phys.2007,331(2-3),254.
31.Uchida,K.;Kageshima,H.;Inokawa,H."Charge-injection effects in a single 4,4"-terphenyldithiol molecule",Jpn.J.Appl.Phys.2005,44(12),8759.
32. Boer, B.; Frank, M. M.; Chabal, Y. J.; Jiang, W.; Garfunkel, E.; Bao, Z. "Metallic Contact Formation for Molecular Electronics: Interactions between Vapor-Deposited Metals and Self-Assembled Monolayers of Conjugated Mono-and Dithiols", Langmuir 2004, 20 (5), 1539.
33. Cuevas, J. C.; Heurich, J.; Pauly, F.; Wenzel, W.; Schoen, G. "Towards a theory of electrical transport through atomic and molecular junctions", Phase Transitions 2004, 77(1-2), 175.
34. Zhitenev, N. B.; Erbe, A.; Bao, Z. "Conductance of molecular nanojunctions",Polym. Prepr. (Am. Chem. Soc, Div. Polym. Chem.) 2003,44 (2), 386.
35. Frank, M. M.; de Boer, B.; Chabal, Y. J.; Bao, Z. "Self-assembled monolayers of conjugated thiols studied by infrared spectroscopy: Structure and metal electrode deposition", Polym. Prepr. (Am. Chem. Soc, Div. Polym. Chem. 2003, 44 (2),383.
36. Zhitenev, N. B.; Erbe, A.; Meng, H.; Bao, Z. "Gated molecular devices using self-assembled monolayers", Nanotechnology 2003,14 (2), 254.
37. Sutton, A. E.; Clardy, J. "The synthesis of potentially selective inhibitors of dihydroorotate dehydrogenase. The utilization of chemoselective Suzuki cross-coupling reactions in a parallel synthesis", Tetrahedron Lett. 2001,42, 547.
38. Simoni, D.; Giannini, G.; Baraldi, P. G.; Romagnoli, R.; Roberti, M.; Rondanin,R.; Baruchello, R.; Grisolia, G.; Rossi, M.; Mirizzi, D.; Invidiata, F. P.;Grimaudoe, S.; Tolomeo, M. "A convenient synthesis of unsymmetrically substituted terphenyls of biologically active stilbenes via a double Suzuki cross-coupling protocol", Tetrahedron Lett. 2003, 44, 3005.
39. Taylor, R. H.; Felpin, F. X. "Suzuki-Miyaura Reactions of Arenediazonium Salts Catalyzed by Pd(0)/C. One-Pot Chemoselective Double Cross-Coupling Reactions", Org. Lett. 2007, 9 (15), 2911.
40. Felpin, F. X.; Fouquet, E. "Efficient and Practical Cross-Coupling of ArenediazoniumTetrafluoroborate Salts with Boronic Acids Catalyzed by Palladium(0)/Barium Carbonate",Adv. Synth. Catal. 2008,350, 863.
41. Shimizu, H.; Manabe, K. "Negishi coupling strategy of a repetitive two-step method for oligoarene synthesis", Tetrahedron Lett. 2006, 47, 5927.
42.Rottlander,M.;Knochel,P."Palladium-Catalyzed Cross-Coupling Reactions with Aryl Nonaflates:A Practical Alternative to Aryl Triflates",J.Org.Chem.1998,63,203.
43.Cho,C.H.;Kim,I.S.;Park,K."Preparation of unsymmetrical terphenyls via the nickel-catalyzed cross-coupling of alkyl biphenylsulfonates with aryl Grignard reagents",Tetrahedron 2004,60,4589.
44.Miguez,A.J.M.;Adrio,L.A.;Sousa-Pedrares,A.;Vila,J.M.;Hii,K.K."A Practical and General Synthesis of Unsymmetrical Terphenyls",J.Org.Chem.2007,72,7771.
45.Galda,P.;Rehahn,M."A versatile palladium catalyzed synthesis of n-alkyl-substituted oligo-p-phenyls",Synthesis 1996,614.
46.Lopez-Romero,J.M.;Rico,R.;Martmez-Mallorqum,R.;Hierrezuelo,J.;Guillen,E.;Cai,C.;Oteroc,J.C.;Lopez-Tocon,I."Synthesis of penta-p-phenylenes with oligo(ethylene glycol) side chains",Tetrahedron Lett.2007,48,6075.
47.Banerjee,M.;Shukla,R.;Rathore,R."Synthesis,Optical,and Electronic Properties of Soluble Poly-p-phenylene Oligomers as Models for Molecular Wires",J.Am.Chem.Soc.2009,131(5),1780.
48.Hosoi,Y.;Koch,N.;Sakurai,Y.;Ishii,H.;Kampen,T.U.;Salvan,G.;Zahn,D.R.T.;Leising,G.;Ouchi,Y.;Seki,K."Structural study of thin films of neutral and potassium-doped oligophenylenes on Cu(100)",Surf.Sci.2005,589,19.
49.Bouzakraouia,S.;Bouzzinea,S.M.;Bouachrinea,M.;Hamidi,M."Density functional theory study of conformational and opto-electronic properties of oligo-para-phenylenes",J.Mol.Struct.THEOCHEM 2005,725,39.
50.Luke,V.;Aquino,A.J.A.;Lischka,H.;Kauffmann,H.F."Dependence of Optical Properties of Oligo-para-phenylenes on Torsional Modes and Chain Length",J.Phys.Chem.B 2007,111(28),7954.
51.Niko,A.;Meghdadi,F.;Ambrosch-Draxl,C.;Vogl,P.;Leising,G."Optical absorbance of oriented thin films",Synth.Met.1996,76,177.
52.Yanagia,H.;Okamoto,S."Orientation-controlled organic electroluminescence of p-sexiphenyl films",Appl.Phys.Lett.1997,71(18),2563.
53. Schiek, M.; Al-Shamery, K.; L(?)tzen, A. "Synthesis of Symmetrically and Unsymmetrically para-Functionalized p-Quaterphenylenes", Synthesis 2007, 4,613.
54. Wallmann, I.; chiek, M.; Koch, R.; L(?)tzen, A. "Synthesis of Monofunctionalized p-Quaterphenyls", Synthesis 2008, 75,2446.
55. Schiek, M.; Balzer, F.; Al-Shamery, K.; Lutzen, A.; Rubahn, H. G."Light-emitting organic nanoaggregates from functionalized p-quaterphenylenes",Soft Matter 2008, 4,277.
56. Schiek, M.; Balzer, R; Al-Shamery, K.; Brewer, J.; Lutzen, A.; Rubahn, H. G."Organic Molecular Nanotechnology", Small 2008,4,176.
57. Wallmann, I.; Schnakenburg, G.; Lutzen, A. "Synthesis of Functionalized Oligophenylenes and Oligoarylenes Bearing Heteroaryl Groups", Synthesis, 2009,7,79.
58. Katagiri, T.; Ota, S.; Ohira, T.; Yamao, T.; Hotta, S. "Synthesis of thiophene/phenylene co-oligomers. V. Functionalization at molecular terminals toward optoelectronic device applications", J. Heterocycl. Chem. 2007, 44 (4),853.
59. Mushrush, M.; Facchetti, A.; Lefenfeld, M.; Katz, H. E.; Marks, T. J. "Easily Processable Phenylene-Thiophene-Based Organic Field-Effect Transistors and Solution-Fabricated Nonvolatile Transistor Memory Elements", J. Am. Chem. Soc.2003, 725 (31), 9414.
60. Yamao, T.; Miki, T.; Akagami, H.; Nishimoto, Y.; Ota, S.; Hotta, S. "Direct Formation of Thin Single Crystals of Organic Semiconductors onto a Substrate",Chem. Mater. 2007,19 (15), 3748.
61. Yamao, T.; Shimizu, Y.; Terasaki, K.; Hotta, S. "Organic light-emitting field-effect transistors operated by alternating-current gate voltages", Adv.Mater. 2008,20(21), 4109.
62. Dingemans, T. J.; Bacher, A.; Thelakkat, M.; Pedersen, L. G.; Samulski, E. T.;Schmidt, H. W. "Spectral tuning of light emitting diodes with phenyl-thiophenes",Synth. Met. 1999, 705 (3), 171.
63.Himmatsu,T.;Shimada,T.;Hotta,S.;Yanagi,H."Photolttminescence dynamics of thiophene/phenylene co-oligomer thin films based on Foerster energy transfer",Thin Solid Films 2008,516(9),2700.
64.Yamao,T.;Taniguchi,Y.;Yamamoto,K.;Miki,T.;Ohira,T.;Hotta,S."Polarized emissions from single crystals of thiophene/phenylene co-oligomers measured by microspectroscopy",Japn.J.Appl.Phys.2008,47(6),4719.
65.Yamao,T.;Taniguchi,Y.;Yamamoto,K.;Miki,T.;Ota,S.;Hotta,S.;Goto,M.;Azumi,R."Anisotropic refractive indices of organic crystals of thiophene/phenylene co-oligomers determined by microspectroscopic measurements",Japn.J.Appl.Phys.2007,46(11),7478.
66.Shimizu,K.;Hoshino,D.;Hotta,S."Unusually narrowed emission lines from a single crystal of thiophene/phenylene co-oligomer",Appl.Phys.Lett.2003,83(22),4494.
67.Ichikawa,M.;Hibino,R.;Inoue,M.;Haritani,T.;Hotta,S.;Koyama,T.;Taniguchi,Y."Improved crystal-growth and emission gain-narrowing of thiophene/phenylene co-oligomers",Adv.Mater.2003,15(3),213.
68.Hibino,R.;Nagawa,M.;Hotta,S.;Ichikawa,M.;Koyama,T.;Taniguchi,Y."Emission gain-narrowing from melt-recrystallized organic semiconductors",Adv.Mater.2002,14(2),119.
69.Yanagi,H.;Araki,Y.;Ohara,T.;Hotta,S.;Ichikawa,M.;Taniguchi,Y."Comparative carrier transport characteristics in organic field-effect transistors with vapor-deposited thin films and epitaxially grown crystals of biphenyl-capped thiophene oligomers",Adv.Funct.Mater.2003,13(10),767.
70.Stuhr-Hansen,N.;Sφrensen,J.K.;Moth-Poulsen,K.;Christensen,J.B.;Bjφrnholm,T.;Nielsen,M.B."Synthetic protocols and building blocks for molecular electronics",Tetrahedron 2005,61,12288.
71.Mayor,M.;Weber,H.B.;Reichert,J.;Elbing,M.;Hanisch,C.;Beckmann,D.;Fischer,M."Electric Current through a Molecular Rod-Relevance of the Position of the Anchor Groups",Angew.Chem.lnt.Ed.2003,42,5834.
72.Weibel,N.;Btaszczyk,A.;H(a|¨)nisch,C.;Mayor,M.;Pobelov,I.;Wandlowski,T.;Chen,F.;Tao,N."Redox-Aetive Catechol-Functionalized Molecular Rods: Suitable Protection Groups and Single-Molecule Transport Investigations", Eur. J.Org. Chem. 2008,136.
73. Ciszek, J. W.; Tour, J. M. "Synthesis of ladder polyaromatics as new molecular device candidates", Tetrahedron Lett. 2004, 45,2801.
74. Yamaguchi, Y.; Ochi, T.; Wakamiya, T.; Matsubara, Y.; Yoshida, Z. "New Fluorophores with Rod-Shaped Polycyano (?)-Conjugated Structures: Synthesis and Photophysical Properties", Org. Lett. 2006,8 (4), 717.
75. Zhu, Y.; Gergel, N.; Majumdar, N.; Harriott, L. R.; Bean, J. C.; Pu, L. "First Optically Active Molecular Electronic Wires", Org. Lett. 2006, 8 (3), 355.
76. Wang, E.; Li, H.; Hu, W.; Zhu, D. "Synthesis and Characterization of New Type Molecular Wires with Tetrathiafulvalene as Redox Center", J. Polym. Sci., Part A:Polym. Chem. 2006, 44 (8), 2707.
77. Giacalone, F.; Herranz, M. A.; Gruter, L.; Gonzalez, M. T.; Calame, M.;Schonenberger, C.; Arroyo, C. R.; Rubio-Bollinger, G.; Velez, M.; Agrait, N.;Martin, N. "Tetrathiafulvalene-based molecular nanowires", Chem. Commun.2007,4854.
78. Shi, Z. F.; Wang, L. J.; Wang, H.; Cao, X. P.; Zhang, H. L. "Synthesis of Oligo(phenyleneethynylene)s with Dendrimer "Shells" for Molecular Electronics", Org. Lett. 2007, 9 (4), 595.
79. Chandra, K. L.; Zhang, S.; Gorman, C. B. "An effective, orthogonal deprotection strategy for differentially functionalized, linear and Y-shaped oligo phenylene ethynylenes", Tetrahedron 2007, 63, 7120.
80. Hsung, R. P.; Chidsey, C. E. D.; Sita, L. R. "Synthesis and Characterization of Unsymmetric Ferrocene-Terminated Phenylethynyl Oligomers Cp_2Fe-[C.tplbond.C-C_6H_4]n-X, (X= SH, SMe, SOMe, and SO_2Me)",Organometallics 1995,14 (10), 4808.
81. Vollmann, M.; Butenschon, H. "Synthesis of a functionalized dialkynylferrocene for molecular electronics", C. R. Chimie 2005, 8,1282.
82. Engtrakul, C.; Sita, L. R. "Ferrocene-Based Nanoelectronics: Regioselective Syntheses and Electrochemical Characterization of -Monothiol and -Dithiol,Phenylethynyl-Conjugated, 2, 5-Diethynylpyridyl- and Pyridinium-Linked Diferrocene Frameworks Having an End-to-End Distance of 4 nm",Organometallics 2008,27 (5), 927.
83. Gryko, D. T.; Clausen, C.; Roth, K. M.; Dontha, N.; Bocian, D. F.; Kuhr, W. G.;Lindsey, J. S. "Synthesis of "Porphyrin-Linker-Thiol" Molecules with Diverse Linkers for Studies of Molecular-Based Information Storage", J. Org. Chem.2000, 65 (22), 7345.
84. Kang, S. H.; Ma, H.; Kang, M. S.; Kim, S. K.; Jen, A. K. Y.; Zareie, M. H.;Sarikaya, M. "Ordered Self-Assembly and Electronic Behavior of C60-Anthrylphenylacetylene Hybrid",Angew. Chem. Int. Ed. 2004, 43,1512.
85. Shirai, Y.; Sasaki, T.; Guerrero, J. M.; Yu, B. C.; Hodge, P.; Tour, J. M."Synthesis and Photoisomerization of Fullerene and Oligo(phenylene ethynylene)Azobenzene Derivatives", Nano 2008,2 (1), 97.
86. Flatt, A. K.; Dirk, S. M.; Henderson, J. C.; Shen, D. E.; Su, J.; Reed, M. A., Tour,J. M. "Synthesis and testing of new end-functionalized oligomers for molecular electronics", Tetrahedron 2003,59, 8555.
87. Yu, B. C.; Shirai, Y.; Tour, J. M. "Syntheses of new functionalized azobenzenes for potential molecular electronic devices", Tetrahedron 2006, 62, 10303.
88. Hanks, T.; Glish, L.; Singh, S.; Johnson, D.; Wright, L. "Conducting polymers as substrates for surface-mounted molecular devices", Synth. Metal. 2005,153,177.
89. Hortholary, C.; Coudret, C. "An Approach to Long and Unsubstituted Molecular Wires: Synthesis of Redox-Active, Cationic Phenylethynyl Oligomers Designed for Self-Assembled Monolayers", J. Org. Chem. 2003, 68 (6), 2167.
90. Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. "Large on-off ratios and negative differential resistance in a molecular electronic device", Science 1999,286(5444), 1550.
91. Chen, J.; Wang, W.; Reed. M. A.; Rawlett, A. M.; Price, D. W.; Tour, J. M."Room-temperature negative differential resistance in nanoscale molecular junctions",Appl. Phys. Lett. 2000, 77(8), 1224.
92. Fan, F. R. F.; Yang, J.; Dirk, S. M.; Price, D. W.; Kosynkin, D.; Tour, J. M.; Bard,A. J. "Determination of the Molecular Electrical Properties of Self-Assembled Monolayers of Compounds of Interest in Molecular Electronics", J. Am. Chem.Soc. 2001,123, 2454.
93. Tour, J. M.; Rawlett, A. M.; Kozaki, M.; Yao, Y.; Jagessar, R. C; Dirk, S. M.;Price, D. W. ; Reed, M. A.; Zhou, C. W.; Chen, J.; Wang, W.; Campbell, I."Synthesis and Preliminary Testing of Molecular Wires and Devices", Chem. Eur.J. 2001, 7(23), 5118.
94. Dirk, S. M.; Price, D. W.; Chanteau, J. S.; Kosynkin, D. V.; Tour, J. M."Accoutrements of a molecular computer: switches, memory components and alligator clips", Tetrahedron 2001, 57, 5109.
95. Price, D. W.; Dirk, J. S. M.; Maya, F.; Tour, J. M. "Improved and new syntheses of potential molecular electronics devices", Tetrahedron 2003, 59,2497.
96. Price, D. W.; Tour, J. M. "Biphenyl- and fluorenyl-based potential molecular electronic devices", Tetrahedron 2003,59, 3131.
97. Maya, F.; Tour, J. M. "Synthesis of terphenyl oligomers as molecular electronic device candidates", Tetrahedron 2004, 60, 81.
98. Flatt, A. K.; Yao, Y.; Maya, F.; Tour, J. M. "Orthogonally Functionalized Oligomers for Controlled Self-Assembly", J. Org. Chem. 2004, 69 (5), 1752.
99. Maya, F.; Chanteau, S. H.; Cheng, L.; Stewart, M. P.; Tour, J. M. "Synthesis of Fluorinated Oligomers toward Physical Vapor Deposition Molecular Electronics Candidates", Chem. Mater. 2005, 17 (6), 1331.
100.Blaszczyk, A.; Chadim, M.; Hanisch, C.; Mayor, M. "Synthesis of Macrocyclic Molecular Rods as Potential Electronic Devices", Eur. J. Org. Chem. 2006, 3809.
101.Blaszczyk, A.; Fischer, M.; Hanisch, C.; Mayor, M. "The Synthesis of Molecular Rods with a Transversal Push-Pull System", Eur. J. Org. Chem. 2007,2630.
102.Stapleton, J. J.; Harder, P.; Daniel, T. A.; Reinard, M. D.; Yao, Y.; Price, D. W.;Tour, J. M.; Allara, D. L. "Self-Assembled Oligo(phenylene-ethynylene) Molecular Electronic Switch Monolayers on Gold: Structures and Chemical Stability", Langmuir 2003,19, 8245.
103.Cheng, L.; Yang, J.; Yao, Y.; Price, D. W.; Dirk, J. S. M.; Tour, J. M."Comparative Study of Electrochemically Directed Assembly versus Conventional Self-Assembly of Thioacetyl-Terminated Oligo(phenylene ethynylene)s on Gold and Platinum Surfaces", Langmuir 2004, 20, 1335.
104.Fan, F. R. F.; Lai, R. Y.; Cornil, J.; Karzazi, Y.; Bredas, J. L.; Cai, L.; Cheng, L.;Yao, Y.; Price, D. W.; Dirk, J. S. M.; Tour, J. M.; Bard, A. J. "Electrons Are Transported through Phenylene-Ethynylene Oligomer Monolayers via Localized Molecular Orbitals", J. Am. Chem. Soc. 2004,126, 2568.
105.Xiao, X.; Nagahara, L. A.; Rawlett, A. M.; Tao, N. "Electrochemical Gate-Controlled Conductance of Single Oligo(phenylene ethynylene)s", J. Am.Chem. Soc. 2005,127, 9235.
106.Majumdar, N.; Gergel-hackett, N.; Bean, J. C; Harriott, L. R.; Pattanaik, G.;Zangari, G.; Yao, Y.; Tour, J. M. "The Electrical Behavior of Nitro Oligo(Phenylene Ethynylene)'s in Pure and Mixed Monolayers", J. Electron.Mater. 2006, 35 (1), 140.
1.Hassan,J.;Sevignon,M.;Gozzi,C.;Schulz,E.;Lemaire,M."Aryl-Aryl Bond Formation One Century after the Discovery of the Ullmarm Reaction",Chem.Rev.2002,102,1359.
2.Taylor,R.H.;Felpin,F.X."Suzuki-Miyaura Reactions of Arenediazonium Salts Catalyzed by Pd(0)/C.One-Pot Chemoselective Double Cross-Coupling Reactions",Org.Lett.2007,9,2911.
3.Denmark,S.E.;Sweis,R.F."Cross-Coupling Reactions of Alkenylsilanolates.Investigation of the Mechanism and Identification of Key Intermediates through Kinetic Analysis",J.Am.Chem.Soc.2004,126,4876.
4.Littke,A.F.;Dai,C.;Fu,G.C."Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions",J.Am.Chem.Soc.2000,122,4020.
5.Miyaura,N.;Suzuki,A."Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds",Chem.Rev.1995,95,2457.
6.Sttzuki,A."Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles",J.Organomet.Chem.1999,576,147.
7.Barder,T.E.;Walker,S.D.;Martinelli,J.R.;Buchwald,S.L."Catalysts for Suzuki-Miyaura Coupling Processes:Scope and Studies of the Effect of Ligand Structure",J.Am.Chem.Soc.2005,127(13),4685.
8.Feuerstein,M.;Doucet,H.;Santelli,M."Tetraphosphine/palladium-catalysed Suzuki cross-coupling with sterically hindered aryl bromides and arylboronic acids",Tetrahedron Lett.2001,42(38),6667.
9.Liu,J.K."Natural Terphenyls:Developments since 1877",Chem.Rev.2006,106,2209.
10.Chen,B.;Baumeister,U.;Pelzl,G.;Das,M.K.;Zeng,X.;Ungar,G.;Tschierske,C."Carbohydrate Rod Conjugates:Ternary Rod-Coil Molecules Forming Complex Liquid Crystal Structures",J.Am.Chem.Soc.2005,127,16578.
11.Handy,S.T.;Wilson,T.;Muth,A."Disubstituted Pyridines:The Double-Coupling Approach",J.Org.Chem.2007,72,8496.
12.Handy,S.T.;Mayi,D."Regioselective double Suzuki couplings of 4,5-dibromothiophene-2-carboxaldehyde",Tetrahedron Lett.2007,48,8108.
13.Burzicki,G.;Voisin-Chiret,A.S.;Santos,J.S.O.;Rault,S."Synthesis of dihalo bi- and terpyridines by regioselective Suzuki-Miyaura cross-coupling reactions",Tetrahedron 2009,65,5413.
14.Beaumard,F.;Dauban,P.;Dodd,R.H."One-Pot Double Suzuki-Miyaura Couplings:Rapid Access to Nonsymmetrical Tri(hetero)aryl Derivatives",Org.Lett.2009,11(8),1801.
15.Simoni,D.;Giannini,G.;Baraldi,P.G.;Romagnoli,R.;Roberti,M.;Rondanin,R.;Baruchello,R.;Grisolia,G.;Rossi,M.;Mirizzi,D.;Invidiata,F.P.;Grimaudoe,S.;Tolomeo,M."A convenient synthesis of unsymmetrically substituted terphenyls of biologically active stilbenes via a double Suzuki cross-coupling protocol",Tetrahedron Lett.2003,44,3005.
16.Sutton,A.E.;Clardy,J."The synthesis of potentially selective inhibitors of dihydroorotate dehydrogenase.The utilization of chemoselective Suzuki cross-coupling reactions in a parallel synthesis",Tetrahedron Lett.2001,42,547.
17.Cho,C.H.;Kim,I.S.;Park,K."Preparation of tmsyngnetrical terphenyls via the nickel-catalyzed cross-coupling of alkyl biphenylsulfonates with aryl Grignard reagents",Tetrahedron 2004,60,4589.
18.Taylor,R.H.;Felpin,F.X."Suzuki-Miyaura Reactions of Arenediazonium Salts Catalyzed by Pd(0)/C.One-Pot Chemoselective Double Cross-Coupling Reactions",Org.Lett.2007,9(15),2911.
19.Felpin,F.X.;Fouquet,E."Efficient and Practical Cross-Coupling of ArenediazoniumTetrafluoroborate Salts with Boronic Acids Catalyzed by Palladium(0)/Barium Carbonate",Adv.Synth.Catal.2008,350,863.
20.Rottlander,M.;Knochel,P."Palladium-Catalyzed Cross-Coupling Reactions with Aryl Nonaflates:A Practical Alternative to Aryl Triflates",J.Org.Chem.1998,63,203.
21.Shimizu,H.;Manabe,K."Negishi coupling strategy of a repetitive two-step method for oligoarene synthesis",Tetrahedron Lett.2006,47,5927.
22.Miguez,A.J.M.;Adrio,L.A.;Sousa-Pedrares,A.;Vila,J.M.;Hii,K.K."A Practical and General Synthesis of Unsymmetrical Terphenyls",J.Org.Chem.2007,72,7771.
23.Boer,B.D.;Meng,H.;Perepichka,D.F.;Zheng,J.;Frank,M.M.;Chabal,Y.J.;Bao,Z."Synthesis and Characterization of Conjugated Mono- and Dithiol Oligomers and Characterization of Their Self-Assembled Monolayers",Langmuir 2003,19,4272.
24.Hersperger,R.;Dawson,J.;Mueller,T."Synthesis of 4-(8-benzo[1,2,5]oxadiazol-5-yl-[1,7]naphthyridine-6-yl)-benzoic Acid:a Potent and Selective Phosphodiesterase Type 4D Inhibitor",Bioorg.Med.Chem.Lett.2002,12,233.
25.Manley,P.W.;Acemoglu,M.;Marterer,W.;Pachinger,W."Large-Scale Negishi Coupling as Applied to the Synthesis of PDE-472,an Inhibitor of Phosphodiesterase Type 4D",Org.Process Res.Dev.2003,7,436.
26.Vyas,P.V.;Bhatt,A.K.;Ramachandraiah,G.;Bedekar,A.V."Environmentally benign chlorination and bromination of aromatic amines,hydrocarbons and naphthols",Tetrahedron Lett.2003,44,4085.
27.Toda,F.;Schmeyers,J."Selective solid-state brominations of anilines and phenols",Green Chem.2003,5,701.
28.Wilson,J.G.;Hunt,F.C."Iminodiacetic acid derivatives of benzimidazole.Synthesis of N-(benzimidazol-2-ylmethyl)iminodiacetic acids",Aust.J.Chem.1983,36,2317.
29.Flatt,A,K.;Yao,Y.;Maya,F.;Tour J.M."Orthogonally Functionalized Oligomers for Controlled Self-Assembly",J.Org.Chem.2004,69,1752.
30.Castillo,R.;Reyes,M.J.;Izquierdo,M.L.;Alvarez-Builla,J."Suzuld reaction on pyridinium N-haloheteroarylaminides:regioselective synthesis of 3,5-disubstituted 2-aminopyrazines",Tetrahedron 2008,64,1351.
31.Thomas,A.P.;Roberts,D.A.;Thomason,D.A."The synthesis and biological activity of tetrahydroquinoline angiotensin Ⅱ antagonists containing a substituted biphenyltetrazole group",Bioorg.Med Chem.Lett.1994,4(21),2615.
32.Urawa,Y.;Naka,H.;Miyazawa,M.;Souda,S.;Ogura,K."Investigations into the Suzuki-Miyaura coupling aiming at multikilogram synthesis of E2040 using (o-cyanophenyl)boronic esters",J.Organomet.Chem.2002,653,269.
33.Gallardo-Godoy,A.;Torres-Altoro,M.I.;White,K.J.;Barker,E.L.;Nichols,D.E."1-Methylpyridinium-4-(4-phenylmethanethiosulfonate) iodide,MTS-MPP+,a novel scanning cysteine accessibility method(SCAM) reagent for monoamine transporter studies",Bioorg.Med.Chem.2007,15,305.
34.Percec,V.;Bera,T.K.;De,B.B.;Sanai,Y.;Smith,J.;Holerca,M.N.;Barboiu,B."Synthesis of Functional Aromatic Multisulfonyl Chlorides and Their Masked Precursors",J.Org.Chem.2001,66,2104.
35.Pema,G.J.;Kilburn,J.D.;Essex,J.W.;Mortishire-Smith,R.J.;Rowley,M."Stabilization of a Cis Amide Bond in a Host-Guest Complex",J.Am.Chem.Soc.1996,118(42),10220.
36.Tellier,F.;Sauvetre,R.;Normant,J.F."Synthese stereospecifique de dienes fluores",J.Organomet.Chem.1985,292(1-2),19.
37.Pommerehne,J.;Vestweber,H.;Guss,W.;Mahrt,R.F.;Baessler,H.;Porsch,M.;Daub,J."Efficient two layer LEDs on a polymer blend basis",Adv.Mater 1995,7(6),551.
38.Leeuw,D.M.;Simenon,M.M.J.;Brown,A.R.;Einerhand,R.E.F."Stability of n-type doped conducting polymers and consequences for polymeric microelectronic devices",Synth.Metal.1997,87(1),53.
39.Agrawal,A.K.;Jenekhe,S.A."Electrochemical Properties and Electronic Structures of Conjugated Polyquinolines and Polyanthrazolines",Chem.Mater 1996,8,579.
1.Cuff,L.;Kertesz,M."Ab Initio Oligomer Approach to Vibrational Spectra of Polymers:Comparison of Helical and Planar Poly(p-phenylene)",Macromolecules 1994,27(3),762.
2.Schiek,M.;Balzer,F.;Al-Shamery,K.;Brewer,J.;L(u|¨)tzen,A.;Rubahn,H.G."Organic Molecular Nanotechnology",Small 2008,4,176.
3.Schiek,M.;Balzer,F.;Al-Shamery,K.;L(u|¨)tzen,A.;Rubahn,H.G."Light-emitting organic nanoaggregates from functionalized p-quaterphenylenes",Soft Matter 2008,4,277.
4.Banerjee,M.;Shulda,R.;Rathore,R."Synthesis,Optical,and Electronic Properties of Soluble Poly-p-phenylene Oligomers as Models for Molecular Wires",J.Am.Chem.Soc.2009,131(5),1780.
5.Wallmann,I.;chiek,M.;Koch,R.;L(u|¨)tzen,A."Synthesis of Monofunctionalized p-Quaterphenyls",Synthesis 2008,15,2446.
6.Schiek,M.;A1-Shamery,K.;L(u|¨)tzen,A."Synthesis of Symmetrically and Unsymmetrically para-Functionalized p-Quaterphenylenes",Synthesis 2007,4,613.
7.Wallmann,I.;Schnakenburg,G.;L(u|¨)tzen,A."Synthesis of Functionalized Oligophenylenes and Oligoarylenes Bearing Heteroaryl Groups",Synthesis,2009,1,79.
8.Dingemans,T.J.;Bacher,A.;Thelakkat,M.;Pedersen,L.G.;Samulski,E.T.;Schmidt,H.W."Spectral tuning of light emitting diodes with phenyl-thiophenes",Synth.Met.1999,105,171.
9.Katagiri,T.;Ota,S.;Ohira,T.;Yamao,T.;Hotta,S."Synthesis of thiophene/phenylene co-oligomers.V.Functionalization at molecular terminals toward optoelectronic device applications",J.Heterocycl.Chem.2007,44(4),853.
10.Jayakannan,M.;Dongen,J.L.J.;Janssen,R.A.J."Optocal,"Optical,electrochemical,magnetic,and conductive properties of new polyindolocarbazoles and polydiindolocarbazoles",Macromol.Chem.Phys.2006,207,166.
11.Lightowler,S.;Hird,M."Palladium-Catalyzed Cross-Coupling Reactions in the Synthesis of Novel Aromatic Polymers",Chem.Mater.2004,16,3963.
12.Todd,M.H.;Balasubramanian,S.;Abell,C."Studies on the synthesis,characterization and reactivity of aromatic diboronic acid",Tetrahedron Lett.1997,38,6781.
13.Forster,M.;Annan,K.O.;Scherf,U."Conjugated Ladder Polymers Containing Thienylene Units",Macromolecules 1999,32(9),3159.
14.Kirschbaum,T.;Azumi,R.;Osteritz,E.M.;Bauerle,P."Synthesis and characterization of structurally defined head-to-tail coupled oligo(3-alkylthiophenes)",New J.Chem.1999,241.
15.Jayakannan,M.;Dongen,J.L.J.;Janssen,R.A.J."Mechanistic Aspects of the Suzuki Polycondensation of Thiophenebisboronic Derivatives and Diiodobenzenes Analyzed by MALDI-TOF Mass Spectrometry", Macromolecules 2001,34,5386.
16.Hellberg,J.;Remonen,T.;Allared,F.;Sl(a|¨)tt,J.;Svensson,M."Synthesis of 2,3-Dihydrothieno[2,3-b]-1,4-dithiine,2,3-Dihydrothieno-[3,2-b]-1,4-oxathiine,2,3-Dihydrothieno[2,3-b]-1,4-oxathiine and Their Transformation into Corresponding End-Capped Oligomers",Synthesis 2003,14,2199.
1.Shi,Z.F.;Wang,L.J.;Wang,H.;Cao,X.P.;Zhang,H.L."Synthesis of Oligo(phenyleneethynylene)s with Dendrimer "Shells" for Molecular Electronics",Org.Lett.2007,9(4),595.
2.Maya,F.;Chanteau,S.H.;Cheng,L.;Stewart,M.P.;Tour,J.M."Synthesis of Fluorinated Oligomers toward Physical Vapor Deposition Molecular Electronics Candidates",Chem.Mater.2005,17(6),1331.
3.Flatt,A.K.;Yao,Y.;Maya,F.;Tour J.M."Orthogonally Functionalized Oligomers for Controlled Self-Assembly",J.Org.Chem.2004,69,1752.
4.江浪,黄桂芳,李洪祥,李小凡,胡文平,刘云祈,朱道本。“自组装分子电子器件”,化学进展,2005,1,172.
5. Cygan, M. T.; Dunbar, T. D.; Arnold, J. J.; Bumm, L. A.; Shedlock, N. F.; Burgin,T. P.; Jones, L., II; Allara, D. L.; Tour, J. M.; Weiss, P. S. "Insertion, Conductivity,and Structures of Conjugated Organic Oligomers in Self-Assembled Alkanethiol Monolayers on Au{111}",J. Am. Chem. Soc. 1998,120 (12), 2721.
6. Reed, M. A.; Chen, J.; Rawlett, A. M.; Price, D. W.; Tour, J. M. "Molecular random access memory cell", Appl. Phys. Lett. 2001, 78 (23), 3735.
7. Chen, J.; Reed, M. A. "Electronic transport of molecular systems", Chem. Phys.2002,281 (2-3), 127.
8. Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. "Large on-off ratios and negative differential resistance in a molecular electronic device", Science 1999,255(5444), 1550.
9. Chen, J.; Wang, W.; Reed. M. A.; Rawlett, A. M.; Price, D. W.; Tour, J. M."Room-temperature negative differential resistance in nanoscale molecular junctions", Appl. Phys. Lett. 2000, 77 (8), 1224.
10. Maya, F.; Tour, J. M. "Synthesis of terphenyl oligomers as molecular electronic device candidates", Tetrahedron 2004, 60, 81.
11. Yu, B. C.; Shirai, Y.; Tour, J. M. "Syntheses of new functionalized azobenzenes for potential molecular electronic devices", Tetrahedron 2006, 62,10303.
12. Flatt, A. K.; Dirk, S. M.; Henderson, J. C.; Shen, D. E.; Su, J.; Reed, M. A.; Tour,J. M. "Synthesis and testing of new end-functionalized oligomers for molecular electronics", Tetrahedron 2003, 59, 8555.
13. Fan, F. R. F.; Lai, R. Y.; Cornil, J.; Karzazi, Y.; Bredas, J. L.; Cai, L.; Cheng, L.;Yao, Y.; Price, D. W.; Dirk, J. S. M.; Tour, J. M.; Bard, A. J. "Electrons Are Transported through Phenylene-Ethynylene Oligomer Monolayers via Localized Molecular Orbitals", J. Am. Chem. Soc. 2004,126,2568.
14. Seminario, J. M.; Zacarias, A. G.; Tour, J. M. "Theoretical Study of a Molecular Resonant Tunneling Diode", J. Am. Chem. Soc. 2000,122 (13), 3015.
15. Lewis, P. A.; Inman, C. E.; Maya, F.; Tour, J. M.; Hutchison, J. E.; Weiss, P. S."Molecular Engineering of the Polarity and Interactions of Molecular Electronic Switches",J. Am. Chem. Soc. 2005, 727(49), 17421.
16. Sonogashira, K.; Tohda, Y.; Hagihara, N. "Convenient synthesis of acetylenes. Catalytic substitutions of acetylenic hydrogen with bromo alkenes, iodo arenes, and bromopyridines", Tetrahedron Lett. 1975,50,4467.
17. Yi, C; Hua, R. "Efficient Copper-Free PdCl_2(PCy_3)_2-Catalyzed Sonogashira Coupling of ArylChlorides with Terminal Alkynes", J. Org. Chem. 2006, 71,2535.
18. Bennani, Y.; Anderson, J. T.; Wang, J.; Campbell, M. G. "Preparation of 4-piperidinol tertiary amines as histamine 3 receptor inhibitors for the treatment of obesity and others DNA disorders", WO2006071750 A1 (2006)
19. Shi, Z. F.; Wang, L. J.; Wang, H.; Cao, X. P.; Zhang, H. L. "Synthesis of Oligo(phenylene ethynylene)s with Dendrimer "Shells" for Molecular Electronics", Org. Lett. 2007, 9 (4), 595.
20. Percec, S.; Getty, R.; French, R. H.; Lustig, S. "Synthesis and characterization of substituted oligomers of phenylene ethynylenes", Polym. Prepr. (Am. Chem. Soc,Div. Polym. Chem.) 2004, 45 (2), 537.
21. Percec, S.; Getty, R.; Marshall, W.; Skidd, G.; French, R. "Synthesis, structural analysis, and self-assembly of phenylene ethynylene oligomers and their -F, -CF3,and -CH3 substituted derivatives", J. Polym. Sci., Part A: Polym. Chem. 2004, 42(3),541.
22. Wu, J.; Chi, C.; Wang, X.; Li, J.; Zhao, X.; Wang, F. "A one-pot procedure to prepare S-protected 4-iodothiophenols", Synth. Commun. 2000,30 (23), 4293.
23. Hsung, R. P.; Chidsey, C. E. D.; Sita, L. R. "Synthesis and Characterization of Unsymmetric Ferrocene-Terminated Phenylethynyl Oligomers Cp_2Fe-[C~0C-C_6H_4]n-X, (X = SH, SMe, SOMe, and SO2Me)", Organometallics 1995,14 (10), 4808.
24. Taher, D.; Walfort, B.; Lang, H. "Rigid-rod structured palladium complexes",Inorg. Chim. Acta 2006, 359 (6), 1899.
25. Hortholary, C.; Coudret, C. "An Approach to Long and Unsubstituted Molecular Wires: Synthesis of Redox-Active, Cationic Phenylethynyl Oligomers Designed for Self-Assembled Monolayers", J. Org. Chem. 2003, 68 (6), 2167.
26.Negishi, E.; Anastasia, L. "Palladium-Catalyzed Alkynylation", Chem. Rev. 2003,705(5), 1979.
27.Flatt, A. K.; Yao, Y.; Maya, F.; Tour, J. M. "Orthogonally Functionalized Oligomers for Controlled Self-Assembly",J. Org. Chem. 2004, 69, 1752.
28. Weber, H. B.; Reichert, J.; Weigend, F.; Ochs, R.; Beckmann, D.; Mayor, M.;Ahlrichs, R.; Lohneysen, H. V. "Electronic transport through single conjugated molecules", Chem. Phys. 2002,281,113.
29. Price, D. W.; Dirk, J. S. M.; Maya, F.; Tour, J. M. "Improved and new syntheses of potential molecular electronics devices", Tetrahedron 2003, 59,2497.
2. Kosugi, M; Sasazawa, K.; Shimizu, Y.; Migita, T. "Reactions of allyltin compounds. III. Allylation of aromatic halides with allyltributyltin in the presence of tetrakis(triphenylphosphine)palladium(0)", Chem. Lett. 1977, (3), 301.
3. Milstein, D.; Stille, J. K. "A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium",J. Am. Chem. Soc. 1978,100, 3636.
4. Beletskaya, I. P. Cheprakov, A. V. "The Heck Reaction as a Sharpening Stone of Palladium Catalysis", Chem. Rev. 2000,100 (8), 3009.
5. Chinchilla, R.; Najera, C. "The Sonogashira Reaction: A Booming Methodology in Synthetic Organic Chemistry." Chem. Rev. 2007,107, 874.
6. Miyaura, N.; Suzuki, A. "Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds", Chem. Rev. 1995,95, 2457.
7. Andersch, J.; Tschierske, C. "Synthesis and liquid crystalline properties of novel laterally connected twins", Liq. Cryst. 1996,21 (1), 51.
8. Berry, R. W. H.; Brocklehurst, P.; Burawoy, A. "Electronic spectra of organic molecules and their interpretation", Tetrahedron 1960,10,109.
9. Brocklehurst, P.; Burawoy, A.; Thompson, A. R. "Electronic spectra of organic molecules and their interpretation. VI. Electronic spectra of p-terphenyl and its derivatives", Tetrahedron 1960,10,102.
10. Iguchi, K.; Nozaki, T.; Imamura, A.; Takahashi, S. "The ultraviolet spectra of monohalo-, mononitro-, and monoamino-p-terphenyls", Bull. Chem. Soc. Jpn.1963, 36, 696.
11. Nozaki, T.; Harada, Y. "Synthesis of mononitro-, monoamino-, and monohalo-p-terphenyls, and their solubility and specific gravity", Bull. Chem.Soc. Jpn. 1962,35, 1783.
12. Tavasli, M.; Bettington, S.; Bryce, M. R.; Batsanov, A. S.; Monkman, A. P."Practical Syntheses of N-Hexylcarbazol-2-yl- and -3-yl-boronic Acids, Their Cross-Coupled Products and a Derived Tris-cyclometalated (Pyridin-2-yl)carbazole Iridium(Ⅲ) Complex",Synthesis 2005,10,1619.
13.Krapchetov,D.A.;Ma,H.;Jen,A.K.Y.;Fischer,D.A.;Loo,Y.L."Solvent-Dependent Assembly of Terphenyl- and Quaterphenyldithiol on Gold and Gallium Arsenide",Langmuir 2005,21(13),5887.
14.Boer,B.D.;Meng,H.;Perepichka,D.F.;Zheng,J.;Frank,M.M.;Chabal,Y.J.;Bao,Z."Synthesis and Characterization of Conjugated Mono- and Dithiol Oligomers and Characterization of Their Self-Assembled Monolayers",Langmuir 2003,19,4272.
15.江浪,黄桂芳,李洪祥,李小凡,胡文平,刘云祈,朱道本。“自组装分子电子器件”,化学进展,2005,1,172.
16.Sabatani,E.;Cohen-Boulakia,J.;Bruening,M.;Rubinstein,I."Thioaromatic Monolayers on Gold:A New Family of Self-Assembling Monolayers",Langmuir 1993,9,2974.
17.Himmel,H.J.;Terfort,A.;Woell,C."Fabrication of a Carboxyl-Terminated Organic Surface with Self-Assembly of Functionalized Terphenylthiols:The Importance of Hydrogen Bond Formation",J.Am.Chem.Soc.1998,120(46),12069.
18.Xue,Y.;Datta,S.;Hong,S.;Reifenberger,R.;Henderson,J.I.;Kubiak,C.P."Negative differential resistance in the scanning-tunneling spectroscopy of organic molecules",Phys.Rev.B:Condens.Matter 1999,59(12),R7852.
19.Ishida,T.;Mizutani,W.;Azehara,H.;Sato,F.;Choi,N.;Akiba,U.;Fujihira,M.;Tokumoto,H."Adsorption processes of self-assembled monolayers made from terphenyl thiols",Langmuir 2001,17(24),7459.
20.Scharf,J.;Strehblow,H.H.;Zeysing,B.;Terfort,A."Electrochemical and surface analytical studies of self-assembled monolayers of three aromatic thiols on gold electrodes",J.Solid State Electrochem.2001,5(6),396.
21.Tran,E.;Grave,C.;Whitesides,G.M.;Rampi,M.A."Controlling the electron transfer mechanism in metal-molecules-metal junctions",Electrochim.Acta 2005,50(25-26),4850.
22.Holmlin,R.E.;Ismagilov,R.F.;Haag,R.;Mujica,V.;Ratner,M.A.;Rampi,M.A.;Whitesides,G.M."Correlating electron transport and molecular structure in organic thin films",Angew.Chem.Int.Ed.2001,40(12),2316.
23.Ishida,T.;Mizutani,W.;Choi,N.;Akiba,U.;Fujihira,M.;Tokumoto,H."Structural Effects on Electrical Conduction of Conjugated Molecules Studied by Scanning Tunneling Microscopy",J.Phys.Chem.B 2000,104(49),11680.
24.Hong,S.;Reifenberger,R.;Tian,W.;Datta,S.;Henderson,J.;Kubiak,C.P."Molecular conductance spectroscopy of conjugated,phenyl-based molecules on Au(111):the effect of end groups on molecular conduction",Superlattices Microstruct.2000,28(4),289.
25.Chen,W.;Wang,L.;Huang,C.;Lin,T.T.;Gao,X.Y.;Loh,K.P.;Chen,Z.K.;Wee,A.T.S."Effect of Functional Group(Fluorine) of Aromatic Thiols on Electron Transfer at the Molecule-Metal Interface",J.Am.Chem.Soc.2006,128(3),935.
26.Holmlin,R.E.;Haag,R.;Chabinyc,M.L.;Ismagilov,R.F.;Cohen,A.E.;Terfort,A.;Rampi,M.A.;Whitesides,G.M."Electron Transport through Thin Organic Films in Metal-Insulator-Metal Junctions Based on Self-Assembled Monolayers",J.Am.Chem.Soc.2001,123(21),5075.
27.Cohen,R.;Stokbro,K.;Martin,J.M.L.;Ratner,M.A."Charge Transport in Conjugated Aromatic Molecular Junctions:Molecular Conjugation and Molecule-Electrode Coupling",J.Phys.Chem.C 2007,111(40),14893.
28.Viljas,J.K.;Pauly,F.;Cuevas,J.C."Photoconductance of organic single-molecule contacts",Phys.Rev.B:Condens.Matter 2007,76(3),033403/1.
29.Goto,T.;Degawa,K.;Inokawa,H.;Furukawa,K.;Nakashima,H.;Sumitomo,K.;Aoki,T.;Torimitsu,K."Molecular-mediated single-electron devices operating at room temperature",Jpn.J.Appl.Phys.2006,45(5A),4285.
30.Maiti,S.K."Quantum transport through organic molecules",Chem.Phys.2007,331(2-3),254.
31.Uchida,K.;Kageshima,H.;Inokawa,H."Charge-injection effects in a single 4,4"-terphenyldithiol molecule",Jpn.J.Appl.Phys.2005,44(12),8759.
32. Boer, B.; Frank, M. M.; Chabal, Y. J.; Jiang, W.; Garfunkel, E.; Bao, Z. "Metallic Contact Formation for Molecular Electronics: Interactions between Vapor-Deposited Metals and Self-Assembled Monolayers of Conjugated Mono-and Dithiols", Langmuir 2004, 20 (5), 1539.
33. Cuevas, J. C.; Heurich, J.; Pauly, F.; Wenzel, W.; Schoen, G. "Towards a theory of electrical transport through atomic and molecular junctions", Phase Transitions 2004, 77(1-2), 175.
34. Zhitenev, N. B.; Erbe, A.; Bao, Z. "Conductance of molecular nanojunctions",Polym. Prepr. (Am. Chem. Soc, Div. Polym. Chem.) 2003,44 (2), 386.
35. Frank, M. M.; de Boer, B.; Chabal, Y. J.; Bao, Z. "Self-assembled monolayers of conjugated thiols studied by infrared spectroscopy: Structure and metal electrode deposition", Polym. Prepr. (Am. Chem. Soc, Div. Polym. Chem. 2003, 44 (2),383.
36. Zhitenev, N. B.; Erbe, A.; Meng, H.; Bao, Z. "Gated molecular devices using self-assembled monolayers", Nanotechnology 2003,14 (2), 254.
37. Sutton, A. E.; Clardy, J. "The synthesis of potentially selective inhibitors of dihydroorotate dehydrogenase. The utilization of chemoselective Suzuki cross-coupling reactions in a parallel synthesis", Tetrahedron Lett. 2001,42, 547.
38. Simoni, D.; Giannini, G.; Baraldi, P. G.; Romagnoli, R.; Roberti, M.; Rondanin,R.; Baruchello, R.; Grisolia, G.; Rossi, M.; Mirizzi, D.; Invidiata, F. P.;Grimaudoe, S.; Tolomeo, M. "A convenient synthesis of unsymmetrically substituted terphenyls of biologically active stilbenes via a double Suzuki cross-coupling protocol", Tetrahedron Lett. 2003, 44, 3005.
39. Taylor, R. H.; Felpin, F. X. "Suzuki-Miyaura Reactions of Arenediazonium Salts Catalyzed by Pd(0)/C. One-Pot Chemoselective Double Cross-Coupling Reactions", Org. Lett. 2007, 9 (15), 2911.
40. Felpin, F. X.; Fouquet, E. "Efficient and Practical Cross-Coupling of ArenediazoniumTetrafluoroborate Salts with Boronic Acids Catalyzed by Palladium(0)/Barium Carbonate",Adv. Synth. Catal. 2008,350, 863.
41. Shimizu, H.; Manabe, K. "Negishi coupling strategy of a repetitive two-step method for oligoarene synthesis", Tetrahedron Lett. 2006, 47, 5927.
42.Rottlander,M.;Knochel,P."Palladium-Catalyzed Cross-Coupling Reactions with Aryl Nonaflates:A Practical Alternative to Aryl Triflates",J.Org.Chem.1998,63,203.
43.Cho,C.H.;Kim,I.S.;Park,K."Preparation of unsymmetrical terphenyls via the nickel-catalyzed cross-coupling of alkyl biphenylsulfonates with aryl Grignard reagents",Tetrahedron 2004,60,4589.
44.Miguez,A.J.M.;Adrio,L.A.;Sousa-Pedrares,A.;Vila,J.M.;Hii,K.K."A Practical and General Synthesis of Unsymmetrical Terphenyls",J.Org.Chem.2007,72,7771.
45.Galda,P.;Rehahn,M."A versatile palladium catalyzed synthesis of n-alkyl-substituted oligo-p-phenyls",Synthesis 1996,614.
46.Lopez-Romero,J.M.;Rico,R.;Martmez-Mallorqum,R.;Hierrezuelo,J.;Guillen,E.;Cai,C.;Oteroc,J.C.;Lopez-Tocon,I."Synthesis of penta-p-phenylenes with oligo(ethylene glycol) side chains",Tetrahedron Lett.2007,48,6075.
47.Banerjee,M.;Shukla,R.;Rathore,R."Synthesis,Optical,and Electronic Properties of Soluble Poly-p-phenylene Oligomers as Models for Molecular Wires",J.Am.Chem.Soc.2009,131(5),1780.
48.Hosoi,Y.;Koch,N.;Sakurai,Y.;Ishii,H.;Kampen,T.U.;Salvan,G.;Zahn,D.R.T.;Leising,G.;Ouchi,Y.;Seki,K."Structural study of thin films of neutral and potassium-doped oligophenylenes on Cu(100)",Surf.Sci.2005,589,19.
49.Bouzakraouia,S.;Bouzzinea,S.M.;Bouachrinea,M.;Hamidi,M."Density functional theory study of conformational and opto-electronic properties of oligo-para-phenylenes",J.Mol.Struct.THEOCHEM 2005,725,39.
50.Luke,V.;Aquino,A.J.A.;Lischka,H.;Kauffmann,H.F."Dependence of Optical Properties of Oligo-para-phenylenes on Torsional Modes and Chain Length",J.Phys.Chem.B 2007,111(28),7954.
51.Niko,A.;Meghdadi,F.;Ambrosch-Draxl,C.;Vogl,P.;Leising,G."Optical absorbance of oriented thin films",Synth.Met.1996,76,177.
52.Yanagia,H.;Okamoto,S."Orientation-controlled organic electroluminescence of p-sexiphenyl films",Appl.Phys.Lett.1997,71(18),2563.
53. Schiek, M.; Al-Shamery, K.; L(?)tzen, A. "Synthesis of Symmetrically and Unsymmetrically para-Functionalized p-Quaterphenylenes", Synthesis 2007, 4,613.
54. Wallmann, I.; chiek, M.; Koch, R.; L(?)tzen, A. "Synthesis of Monofunctionalized p-Quaterphenyls", Synthesis 2008, 75,2446.
55. Schiek, M.; Balzer, F.; Al-Shamery, K.; Lutzen, A.; Rubahn, H. G."Light-emitting organic nanoaggregates from functionalized p-quaterphenylenes",Soft Matter 2008, 4,277.
56. Schiek, M.; Balzer, R; Al-Shamery, K.; Brewer, J.; Lutzen, A.; Rubahn, H. G."Organic Molecular Nanotechnology", Small 2008,4,176.
57. Wallmann, I.; Schnakenburg, G.; Lutzen, A. "Synthesis of Functionalized Oligophenylenes and Oligoarylenes Bearing Heteroaryl Groups", Synthesis, 2009,7,79.
58. Katagiri, T.; Ota, S.; Ohira, T.; Yamao, T.; Hotta, S. "Synthesis of thiophene/phenylene co-oligomers. V. Functionalization at molecular terminals toward optoelectronic device applications", J. Heterocycl. Chem. 2007, 44 (4),853.
59. Mushrush, M.; Facchetti, A.; Lefenfeld, M.; Katz, H. E.; Marks, T. J. "Easily Processable Phenylene-Thiophene-Based Organic Field-Effect Transistors and Solution-Fabricated Nonvolatile Transistor Memory Elements", J. Am. Chem. Soc.2003, 725 (31), 9414.
60. Yamao, T.; Miki, T.; Akagami, H.; Nishimoto, Y.; Ota, S.; Hotta, S. "Direct Formation of Thin Single Crystals of Organic Semiconductors onto a Substrate",Chem. Mater. 2007,19 (15), 3748.
61. Yamao, T.; Shimizu, Y.; Terasaki, K.; Hotta, S. "Organic light-emitting field-effect transistors operated by alternating-current gate voltages", Adv.Mater. 2008,20(21), 4109.
62. Dingemans, T. J.; Bacher, A.; Thelakkat, M.; Pedersen, L. G.; Samulski, E. T.;Schmidt, H. W. "Spectral tuning of light emitting diodes with phenyl-thiophenes",Synth. Met. 1999, 705 (3), 171.
63.Himmatsu,T.;Shimada,T.;Hotta,S.;Yanagi,H."Photolttminescence dynamics of thiophene/phenylene co-oligomer thin films based on Foerster energy transfer",Thin Solid Films 2008,516(9),2700.
64.Yamao,T.;Taniguchi,Y.;Yamamoto,K.;Miki,T.;Ohira,T.;Hotta,S."Polarized emissions from single crystals of thiophene/phenylene co-oligomers measured by microspectroscopy",Japn.J.Appl.Phys.2008,47(6),4719.
65.Yamao,T.;Taniguchi,Y.;Yamamoto,K.;Miki,T.;Ota,S.;Hotta,S.;Goto,M.;Azumi,R."Anisotropic refractive indices of organic crystals of thiophene/phenylene co-oligomers determined by microspectroscopic measurements",Japn.J.Appl.Phys.2007,46(11),7478.
66.Shimizu,K.;Hoshino,D.;Hotta,S."Unusually narrowed emission lines from a single crystal of thiophene/phenylene co-oligomer",Appl.Phys.Lett.2003,83(22),4494.
67.Ichikawa,M.;Hibino,R.;Inoue,M.;Haritani,T.;Hotta,S.;Koyama,T.;Taniguchi,Y."Improved crystal-growth and emission gain-narrowing of thiophene/phenylene co-oligomers",Adv.Mater.2003,15(3),213.
68.Hibino,R.;Nagawa,M.;Hotta,S.;Ichikawa,M.;Koyama,T.;Taniguchi,Y."Emission gain-narrowing from melt-recrystallized organic semiconductors",Adv.Mater.2002,14(2),119.
69.Yanagi,H.;Araki,Y.;Ohara,T.;Hotta,S.;Ichikawa,M.;Taniguchi,Y."Comparative carrier transport characteristics in organic field-effect transistors with vapor-deposited thin films and epitaxially grown crystals of biphenyl-capped thiophene oligomers",Adv.Funct.Mater.2003,13(10),767.
70.Stuhr-Hansen,N.;Sφrensen,J.K.;Moth-Poulsen,K.;Christensen,J.B.;Bjφrnholm,T.;Nielsen,M.B."Synthetic protocols and building blocks for molecular electronics",Tetrahedron 2005,61,12288.
71.Mayor,M.;Weber,H.B.;Reichert,J.;Elbing,M.;Hanisch,C.;Beckmann,D.;Fischer,M."Electric Current through a Molecular Rod-Relevance of the Position of the Anchor Groups",Angew.Chem.lnt.Ed.2003,42,5834.
72.Weibel,N.;Btaszczyk,A.;H(a|¨)nisch,C.;Mayor,M.;Pobelov,I.;Wandlowski,T.;Chen,F.;Tao,N."Redox-Aetive Catechol-Functionalized Molecular Rods: Suitable Protection Groups and Single-Molecule Transport Investigations", Eur. J.Org. Chem. 2008,136.
73. Ciszek, J. W.; Tour, J. M. "Synthesis of ladder polyaromatics as new molecular device candidates", Tetrahedron Lett. 2004, 45,2801.
74. Yamaguchi, Y.; Ochi, T.; Wakamiya, T.; Matsubara, Y.; Yoshida, Z. "New Fluorophores with Rod-Shaped Polycyano (?)-Conjugated Structures: Synthesis and Photophysical Properties", Org. Lett. 2006,8 (4), 717.
75. Zhu, Y.; Gergel, N.; Majumdar, N.; Harriott, L. R.; Bean, J. C.; Pu, L. "First Optically Active Molecular Electronic Wires", Org. Lett. 2006, 8 (3), 355.
76. Wang, E.; Li, H.; Hu, W.; Zhu, D. "Synthesis and Characterization of New Type Molecular Wires with Tetrathiafulvalene as Redox Center", J. Polym. Sci., Part A:Polym. Chem. 2006, 44 (8), 2707.
77. Giacalone, F.; Herranz, M. A.; Gruter, L.; Gonzalez, M. T.; Calame, M.;Schonenberger, C.; Arroyo, C. R.; Rubio-Bollinger, G.; Velez, M.; Agrait, N.;Martin, N. "Tetrathiafulvalene-based molecular nanowires", Chem. Commun.2007,4854.
78. Shi, Z. F.; Wang, L. J.; Wang, H.; Cao, X. P.; Zhang, H. L. "Synthesis of Oligo(phenyleneethynylene)s with Dendrimer "Shells" for Molecular Electronics", Org. Lett. 2007, 9 (4), 595.
79. Chandra, K. L.; Zhang, S.; Gorman, C. B. "An effective, orthogonal deprotection strategy for differentially functionalized, linear and Y-shaped oligo phenylene ethynylenes", Tetrahedron 2007, 63, 7120.
80. Hsung, R. P.; Chidsey, C. E. D.; Sita, L. R. "Synthesis and Characterization of Unsymmetric Ferrocene-Terminated Phenylethynyl Oligomers Cp_2Fe-[C.tplbond.C-C_6H_4]n-X, (X= SH, SMe, SOMe, and SO_2Me)",Organometallics 1995,14 (10), 4808.
81. Vollmann, M.; Butenschon, H. "Synthesis of a functionalized dialkynylferrocene for molecular electronics", C. R. Chimie 2005, 8,1282.
82. Engtrakul, C.; Sita, L. R. "Ferrocene-Based Nanoelectronics: Regioselective Syntheses and Electrochemical Characterization of -Monothiol and -Dithiol,Phenylethynyl-Conjugated, 2, 5-Diethynylpyridyl- and Pyridinium-Linked Diferrocene Frameworks Having an End-to-End Distance of 4 nm",Organometallics 2008,27 (5), 927.
83. Gryko, D. T.; Clausen, C.; Roth, K. M.; Dontha, N.; Bocian, D. F.; Kuhr, W. G.;Lindsey, J. S. "Synthesis of "Porphyrin-Linker-Thiol" Molecules with Diverse Linkers for Studies of Molecular-Based Information Storage", J. Org. Chem.2000, 65 (22), 7345.
84. Kang, S. H.; Ma, H.; Kang, M. S.; Kim, S. K.; Jen, A. K. Y.; Zareie, M. H.;Sarikaya, M. "Ordered Self-Assembly and Electronic Behavior of C60-Anthrylphenylacetylene Hybrid",Angew. Chem. Int. Ed. 2004, 43,1512.
85. Shirai, Y.; Sasaki, T.; Guerrero, J. M.; Yu, B. C.; Hodge, P.; Tour, J. M."Synthesis and Photoisomerization of Fullerene and Oligo(phenylene ethynylene)Azobenzene Derivatives", Nano 2008,2 (1), 97.
86. Flatt, A. K.; Dirk, S. M.; Henderson, J. C.; Shen, D. E.; Su, J.; Reed, M. A., Tour,J. M. "Synthesis and testing of new end-functionalized oligomers for molecular electronics", Tetrahedron 2003,59, 8555.
87. Yu, B. C.; Shirai, Y.; Tour, J. M. "Syntheses of new functionalized azobenzenes for potential molecular electronic devices", Tetrahedron 2006, 62, 10303.
88. Hanks, T.; Glish, L.; Singh, S.; Johnson, D.; Wright, L. "Conducting polymers as substrates for surface-mounted molecular devices", Synth. Metal. 2005,153,177.
89. Hortholary, C.; Coudret, C. "An Approach to Long and Unsubstituted Molecular Wires: Synthesis of Redox-Active, Cationic Phenylethynyl Oligomers Designed for Self-Assembled Monolayers", J. Org. Chem. 2003, 68 (6), 2167.
90. Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. "Large on-off ratios and negative differential resistance in a molecular electronic device", Science 1999,286(5444), 1550.
91. Chen, J.; Wang, W.; Reed. M. A.; Rawlett, A. M.; Price, D. W.; Tour, J. M."Room-temperature negative differential resistance in nanoscale molecular junctions",Appl. Phys. Lett. 2000, 77(8), 1224.
92. Fan, F. R. F.; Yang, J.; Dirk, S. M.; Price, D. W.; Kosynkin, D.; Tour, J. M.; Bard,A. J. "Determination of the Molecular Electrical Properties of Self-Assembled Monolayers of Compounds of Interest in Molecular Electronics", J. Am. Chem.Soc. 2001,123, 2454.
93. Tour, J. M.; Rawlett, A. M.; Kozaki, M.; Yao, Y.; Jagessar, R. C; Dirk, S. M.;Price, D. W. ; Reed, M. A.; Zhou, C. W.; Chen, J.; Wang, W.; Campbell, I."Synthesis and Preliminary Testing of Molecular Wires and Devices", Chem. Eur.J. 2001, 7(23), 5118.
94. Dirk, S. M.; Price, D. W.; Chanteau, J. S.; Kosynkin, D. V.; Tour, J. M."Accoutrements of a molecular computer: switches, memory components and alligator clips", Tetrahedron 2001, 57, 5109.
95. Price, D. W.; Dirk, J. S. M.; Maya, F.; Tour, J. M. "Improved and new syntheses of potential molecular electronics devices", Tetrahedron 2003, 59,2497.
96. Price, D. W.; Tour, J. M. "Biphenyl- and fluorenyl-based potential molecular electronic devices", Tetrahedron 2003,59, 3131.
97. Maya, F.; Tour, J. M. "Synthesis of terphenyl oligomers as molecular electronic device candidates", Tetrahedron 2004, 60, 81.
98. Flatt, A. K.; Yao, Y.; Maya, F.; Tour, J. M. "Orthogonally Functionalized Oligomers for Controlled Self-Assembly", J. Org. Chem. 2004, 69 (5), 1752.
99. Maya, F.; Chanteau, S. H.; Cheng, L.; Stewart, M. P.; Tour, J. M. "Synthesis of Fluorinated Oligomers toward Physical Vapor Deposition Molecular Electronics Candidates", Chem. Mater. 2005, 17 (6), 1331.
100.Blaszczyk, A.; Chadim, M.; Hanisch, C.; Mayor, M. "Synthesis of Macrocyclic Molecular Rods as Potential Electronic Devices", Eur. J. Org. Chem. 2006, 3809.
101.Blaszczyk, A.; Fischer, M.; Hanisch, C.; Mayor, M. "The Synthesis of Molecular Rods with a Transversal Push-Pull System", Eur. J. Org. Chem. 2007,2630.
102.Stapleton, J. J.; Harder, P.; Daniel, T. A.; Reinard, M. D.; Yao, Y.; Price, D. W.;Tour, J. M.; Allara, D. L. "Self-Assembled Oligo(phenylene-ethynylene) Molecular Electronic Switch Monolayers on Gold: Structures and Chemical Stability", Langmuir 2003,19, 8245.
103.Cheng, L.; Yang, J.; Yao, Y.; Price, D. W.; Dirk, J. S. M.; Tour, J. M."Comparative Study of Electrochemically Directed Assembly versus Conventional Self-Assembly of Thioacetyl-Terminated Oligo(phenylene ethynylene)s on Gold and Platinum Surfaces", Langmuir 2004, 20, 1335.
104.Fan, F. R. F.; Lai, R. Y.; Cornil, J.; Karzazi, Y.; Bredas, J. L.; Cai, L.; Cheng, L.;Yao, Y.; Price, D. W.; Dirk, J. S. M.; Tour, J. M.; Bard, A. J. "Electrons Are Transported through Phenylene-Ethynylene Oligomer Monolayers via Localized Molecular Orbitals", J. Am. Chem. Soc. 2004,126, 2568.
105.Xiao, X.; Nagahara, L. A.; Rawlett, A. M.; Tao, N. "Electrochemical Gate-Controlled Conductance of Single Oligo(phenylene ethynylene)s", J. Am.Chem. Soc. 2005,127, 9235.
106.Majumdar, N.; Gergel-hackett, N.; Bean, J. C; Harriott, L. R.; Pattanaik, G.;Zangari, G.; Yao, Y.; Tour, J. M. "The Electrical Behavior of Nitro Oligo(Phenylene Ethynylene)'s in Pure and Mixed Monolayers", J. Electron.Mater. 2006, 35 (1), 140.
1.Hassan,J.;Sevignon,M.;Gozzi,C.;Schulz,E.;Lemaire,M."Aryl-Aryl Bond Formation One Century after the Discovery of the Ullmarm Reaction",Chem.Rev.2002,102,1359.
2.Taylor,R.H.;Felpin,F.X."Suzuki-Miyaura Reactions of Arenediazonium Salts Catalyzed by Pd(0)/C.One-Pot Chemoselective Double Cross-Coupling Reactions",Org.Lett.2007,9,2911.
3.Denmark,S.E.;Sweis,R.F."Cross-Coupling Reactions of Alkenylsilanolates.Investigation of the Mechanism and Identification of Key Intermediates through Kinetic Analysis",J.Am.Chem.Soc.2004,126,4876.
4.Littke,A.F.;Dai,C.;Fu,G.C."Versatile Catalysts for the Suzuki Cross-Coupling of Arylboronic Acids with Aryl and Vinyl Halides and Triflates under Mild Conditions",J.Am.Chem.Soc.2000,122,4020.
5.Miyaura,N.;Suzuki,A."Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds",Chem.Rev.1995,95,2457.
6.Sttzuki,A."Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles",J.Organomet.Chem.1999,576,147.
7.Barder,T.E.;Walker,S.D.;Martinelli,J.R.;Buchwald,S.L."Catalysts for Suzuki-Miyaura Coupling Processes:Scope and Studies of the Effect of Ligand Structure",J.Am.Chem.Soc.2005,127(13),4685.
8.Feuerstein,M.;Doucet,H.;Santelli,M."Tetraphosphine/palladium-catalysed Suzuki cross-coupling with sterically hindered aryl bromides and arylboronic acids",Tetrahedron Lett.2001,42(38),6667.
9.Liu,J.K."Natural Terphenyls:Developments since 1877",Chem.Rev.2006,106,2209.
10.Chen,B.;Baumeister,U.;Pelzl,G.;Das,M.K.;Zeng,X.;Ungar,G.;Tschierske,C."Carbohydrate Rod Conjugates:Ternary Rod-Coil Molecules Forming Complex Liquid Crystal Structures",J.Am.Chem.Soc.2005,127,16578.
11.Handy,S.T.;Wilson,T.;Muth,A."Disubstituted Pyridines:The Double-Coupling Approach",J.Org.Chem.2007,72,8496.
12.Handy,S.T.;Mayi,D."Regioselective double Suzuki couplings of 4,5-dibromothiophene-2-carboxaldehyde",Tetrahedron Lett.2007,48,8108.
13.Burzicki,G.;Voisin-Chiret,A.S.;Santos,J.S.O.;Rault,S."Synthesis of dihalo bi- and terpyridines by regioselective Suzuki-Miyaura cross-coupling reactions",Tetrahedron 2009,65,5413.
14.Beaumard,F.;Dauban,P.;Dodd,R.H."One-Pot Double Suzuki-Miyaura Couplings:Rapid Access to Nonsymmetrical Tri(hetero)aryl Derivatives",Org.Lett.2009,11(8),1801.
15.Simoni,D.;Giannini,G.;Baraldi,P.G.;Romagnoli,R.;Roberti,M.;Rondanin,R.;Baruchello,R.;Grisolia,G.;Rossi,M.;Mirizzi,D.;Invidiata,F.P.;Grimaudoe,S.;Tolomeo,M."A convenient synthesis of unsymmetrically substituted terphenyls of biologically active stilbenes via a double Suzuki cross-coupling protocol",Tetrahedron Lett.2003,44,3005.
16.Sutton,A.E.;Clardy,J."The synthesis of potentially selective inhibitors of dihydroorotate dehydrogenase.The utilization of chemoselective Suzuki cross-coupling reactions in a parallel synthesis",Tetrahedron Lett.2001,42,547.
17.Cho,C.H.;Kim,I.S.;Park,K."Preparation of tmsyngnetrical terphenyls via the nickel-catalyzed cross-coupling of alkyl biphenylsulfonates with aryl Grignard reagents",Tetrahedron 2004,60,4589.
18.Taylor,R.H.;Felpin,F.X."Suzuki-Miyaura Reactions of Arenediazonium Salts Catalyzed by Pd(0)/C.One-Pot Chemoselective Double Cross-Coupling Reactions",Org.Lett.2007,9(15),2911.
19.Felpin,F.X.;Fouquet,E."Efficient and Practical Cross-Coupling of ArenediazoniumTetrafluoroborate Salts with Boronic Acids Catalyzed by Palladium(0)/Barium Carbonate",Adv.Synth.Catal.2008,350,863.
20.Rottlander,M.;Knochel,P."Palladium-Catalyzed Cross-Coupling Reactions with Aryl Nonaflates:A Practical Alternative to Aryl Triflates",J.Org.Chem.1998,63,203.
21.Shimizu,H.;Manabe,K."Negishi coupling strategy of a repetitive two-step method for oligoarene synthesis",Tetrahedron Lett.2006,47,5927.
22.Miguez,A.J.M.;Adrio,L.A.;Sousa-Pedrares,A.;Vila,J.M.;Hii,K.K."A Practical and General Synthesis of Unsymmetrical Terphenyls",J.Org.Chem.2007,72,7771.
23.Boer,B.D.;Meng,H.;Perepichka,D.F.;Zheng,J.;Frank,M.M.;Chabal,Y.J.;Bao,Z."Synthesis and Characterization of Conjugated Mono- and Dithiol Oligomers and Characterization of Their Self-Assembled Monolayers",Langmuir 2003,19,4272.
24.Hersperger,R.;Dawson,J.;Mueller,T."Synthesis of 4-(8-benzo[1,2,5]oxadiazol-5-yl-[1,7]naphthyridine-6-yl)-benzoic Acid:a Potent and Selective Phosphodiesterase Type 4D Inhibitor",Bioorg.Med.Chem.Lett.2002,12,233.
25.Manley,P.W.;Acemoglu,M.;Marterer,W.;Pachinger,W."Large-Scale Negishi Coupling as Applied to the Synthesis of PDE-472,an Inhibitor of Phosphodiesterase Type 4D",Org.Process Res.Dev.2003,7,436.
26.Vyas,P.V.;Bhatt,A.K.;Ramachandraiah,G.;Bedekar,A.V."Environmentally benign chlorination and bromination of aromatic amines,hydrocarbons and naphthols",Tetrahedron Lett.2003,44,4085.
27.Toda,F.;Schmeyers,J."Selective solid-state brominations of anilines and phenols",Green Chem.2003,5,701.
28.Wilson,J.G.;Hunt,F.C."Iminodiacetic acid derivatives of benzimidazole.Synthesis of N-(benzimidazol-2-ylmethyl)iminodiacetic acids",Aust.J.Chem.1983,36,2317.
29.Flatt,A,K.;Yao,Y.;Maya,F.;Tour J.M."Orthogonally Functionalized Oligomers for Controlled Self-Assembly",J.Org.Chem.2004,69,1752.
30.Castillo,R.;Reyes,M.J.;Izquierdo,M.L.;Alvarez-Builla,J."Suzuld reaction on pyridinium N-haloheteroarylaminides:regioselective synthesis of 3,5-disubstituted 2-aminopyrazines",Tetrahedron 2008,64,1351.
31.Thomas,A.P.;Roberts,D.A.;Thomason,D.A."The synthesis and biological activity of tetrahydroquinoline angiotensin Ⅱ antagonists containing a substituted biphenyltetrazole group",Bioorg.Med Chem.Lett.1994,4(21),2615.
32.Urawa,Y.;Naka,H.;Miyazawa,M.;Souda,S.;Ogura,K."Investigations into the Suzuki-Miyaura coupling aiming at multikilogram synthesis of E2040 using (o-cyanophenyl)boronic esters",J.Organomet.Chem.2002,653,269.
33.Gallardo-Godoy,A.;Torres-Altoro,M.I.;White,K.J.;Barker,E.L.;Nichols,D.E."1-Methylpyridinium-4-(4-phenylmethanethiosulfonate) iodide,MTS-MPP+,a novel scanning cysteine accessibility method(SCAM) reagent for monoamine transporter studies",Bioorg.Med.Chem.2007,15,305.
34.Percec,V.;Bera,T.K.;De,B.B.;Sanai,Y.;Smith,J.;Holerca,M.N.;Barboiu,B."Synthesis of Functional Aromatic Multisulfonyl Chlorides and Their Masked Precursors",J.Org.Chem.2001,66,2104.
35.Pema,G.J.;Kilburn,J.D.;Essex,J.W.;Mortishire-Smith,R.J.;Rowley,M."Stabilization of a Cis Amide Bond in a Host-Guest Complex",J.Am.Chem.Soc.1996,118(42),10220.
36.Tellier,F.;Sauvetre,R.;Normant,J.F."Synthese stereospecifique de dienes fluores",J.Organomet.Chem.1985,292(1-2),19.
37.Pommerehne,J.;Vestweber,H.;Guss,W.;Mahrt,R.F.;Baessler,H.;Porsch,M.;Daub,J."Efficient two layer LEDs on a polymer blend basis",Adv.Mater 1995,7(6),551.
38.Leeuw,D.M.;Simenon,M.M.J.;Brown,A.R.;Einerhand,R.E.F."Stability of n-type doped conducting polymers and consequences for polymeric microelectronic devices",Synth.Metal.1997,87(1),53.
39.Agrawal,A.K.;Jenekhe,S.A."Electrochemical Properties and Electronic Structures of Conjugated Polyquinolines and Polyanthrazolines",Chem.Mater 1996,8,579.
1.Cuff,L.;Kertesz,M."Ab Initio Oligomer Approach to Vibrational Spectra of Polymers:Comparison of Helical and Planar Poly(p-phenylene)",Macromolecules 1994,27(3),762.
2.Schiek,M.;Balzer,F.;Al-Shamery,K.;Brewer,J.;L(u|¨)tzen,A.;Rubahn,H.G."Organic Molecular Nanotechnology",Small 2008,4,176.
3.Schiek,M.;Balzer,F.;Al-Shamery,K.;L(u|¨)tzen,A.;Rubahn,H.G."Light-emitting organic nanoaggregates from functionalized p-quaterphenylenes",Soft Matter 2008,4,277.
4.Banerjee,M.;Shulda,R.;Rathore,R."Synthesis,Optical,and Electronic Properties of Soluble Poly-p-phenylene Oligomers as Models for Molecular Wires",J.Am.Chem.Soc.2009,131(5),1780.
5.Wallmann,I.;chiek,M.;Koch,R.;L(u|¨)tzen,A."Synthesis of Monofunctionalized p-Quaterphenyls",Synthesis 2008,15,2446.
6.Schiek,M.;A1-Shamery,K.;L(u|¨)tzen,A."Synthesis of Symmetrically and Unsymmetrically para-Functionalized p-Quaterphenylenes",Synthesis 2007,4,613.
7.Wallmann,I.;Schnakenburg,G.;L(u|¨)tzen,A."Synthesis of Functionalized Oligophenylenes and Oligoarylenes Bearing Heteroaryl Groups",Synthesis,2009,1,79.
8.Dingemans,T.J.;Bacher,A.;Thelakkat,M.;Pedersen,L.G.;Samulski,E.T.;Schmidt,H.W."Spectral tuning of light emitting diodes with phenyl-thiophenes",Synth.Met.1999,105,171.
9.Katagiri,T.;Ota,S.;Ohira,T.;Yamao,T.;Hotta,S."Synthesis of thiophene/phenylene co-oligomers.V.Functionalization at molecular terminals toward optoelectronic device applications",J.Heterocycl.Chem.2007,44(4),853.
10.Jayakannan,M.;Dongen,J.L.J.;Janssen,R.A.J."Optocal,"Optical,electrochemical,magnetic,and conductive properties of new polyindolocarbazoles and polydiindolocarbazoles",Macromol.Chem.Phys.2006,207,166.
11.Lightowler,S.;Hird,M."Palladium-Catalyzed Cross-Coupling Reactions in the Synthesis of Novel Aromatic Polymers",Chem.Mater.2004,16,3963.
12.Todd,M.H.;Balasubramanian,S.;Abell,C."Studies on the synthesis,characterization and reactivity of aromatic diboronic acid",Tetrahedron Lett.1997,38,6781.
13.Forster,M.;Annan,K.O.;Scherf,U."Conjugated Ladder Polymers Containing Thienylene Units",Macromolecules 1999,32(9),3159.
14.Kirschbaum,T.;Azumi,R.;Osteritz,E.M.;Bauerle,P."Synthesis and characterization of structurally defined head-to-tail coupled oligo(3-alkylthiophenes)",New J.Chem.1999,241.
15.Jayakannan,M.;Dongen,J.L.J.;Janssen,R.A.J."Mechanistic Aspects of the Suzuki Polycondensation of Thiophenebisboronic Derivatives and Diiodobenzenes Analyzed by MALDI-TOF Mass Spectrometry", Macromolecules 2001,34,5386.
16.Hellberg,J.;Remonen,T.;Allared,F.;Sl(a|¨)tt,J.;Svensson,M."Synthesis of 2,3-Dihydrothieno[2,3-b]-1,4-dithiine,2,3-Dihydrothieno-[3,2-b]-1,4-oxathiine,2,3-Dihydrothieno[2,3-b]-1,4-oxathiine and Their Transformation into Corresponding End-Capped Oligomers",Synthesis 2003,14,2199.
1.Shi,Z.F.;Wang,L.J.;Wang,H.;Cao,X.P.;Zhang,H.L."Synthesis of Oligo(phenyleneethynylene)s with Dendrimer "Shells" for Molecular Electronics",Org.Lett.2007,9(4),595.
2.Maya,F.;Chanteau,S.H.;Cheng,L.;Stewart,M.P.;Tour,J.M."Synthesis of Fluorinated Oligomers toward Physical Vapor Deposition Molecular Electronics Candidates",Chem.Mater.2005,17(6),1331.
3.Flatt,A.K.;Yao,Y.;Maya,F.;Tour J.M."Orthogonally Functionalized Oligomers for Controlled Self-Assembly",J.Org.Chem.2004,69,1752.
4.江浪,黄桂芳,李洪祥,李小凡,胡文平,刘云祈,朱道本。“自组装分子电子器件”,化学进展,2005,1,172.
5. Cygan, M. T.; Dunbar, T. D.; Arnold, J. J.; Bumm, L. A.; Shedlock, N. F.; Burgin,T. P.; Jones, L., II; Allara, D. L.; Tour, J. M.; Weiss, P. S. "Insertion, Conductivity,and Structures of Conjugated Organic Oligomers in Self-Assembled Alkanethiol Monolayers on Au{111}",J. Am. Chem. Soc. 1998,120 (12), 2721.
6. Reed, M. A.; Chen, J.; Rawlett, A. M.; Price, D. W.; Tour, J. M. "Molecular random access memory cell", Appl. Phys. Lett. 2001, 78 (23), 3735.
7. Chen, J.; Reed, M. A. "Electronic transport of molecular systems", Chem. Phys.2002,281 (2-3), 127.
8. Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. "Large on-off ratios and negative differential resistance in a molecular electronic device", Science 1999,255(5444), 1550.
9. Chen, J.; Wang, W.; Reed. M. A.; Rawlett, A. M.; Price, D. W.; Tour, J. M."Room-temperature negative differential resistance in nanoscale molecular junctions", Appl. Phys. Lett. 2000, 77 (8), 1224.
10. Maya, F.; Tour, J. M. "Synthesis of terphenyl oligomers as molecular electronic device candidates", Tetrahedron 2004, 60, 81.
11. Yu, B. C.; Shirai, Y.; Tour, J. M. "Syntheses of new functionalized azobenzenes for potential molecular electronic devices", Tetrahedron 2006, 62,10303.
12. Flatt, A. K.; Dirk, S. M.; Henderson, J. C.; Shen, D. E.; Su, J.; Reed, M. A.; Tour,J. M. "Synthesis and testing of new end-functionalized oligomers for molecular electronics", Tetrahedron 2003, 59, 8555.
13. Fan, F. R. F.; Lai, R. Y.; Cornil, J.; Karzazi, Y.; Bredas, J. L.; Cai, L.; Cheng, L.;Yao, Y.; Price, D. W.; Dirk, J. S. M.; Tour, J. M.; Bard, A. J. "Electrons Are Transported through Phenylene-Ethynylene Oligomer Monolayers via Localized Molecular Orbitals", J. Am. Chem. Soc. 2004,126,2568.
14. Seminario, J. M.; Zacarias, A. G.; Tour, J. M. "Theoretical Study of a Molecular Resonant Tunneling Diode", J. Am. Chem. Soc. 2000,122 (13), 3015.
15. Lewis, P. A.; Inman, C. E.; Maya, F.; Tour, J. M.; Hutchison, J. E.; Weiss, P. S."Molecular Engineering of the Polarity and Interactions of Molecular Electronic Switches",J. Am. Chem. Soc. 2005, 727(49), 17421.
16. Sonogashira, K.; Tohda, Y.; Hagihara, N. "Convenient synthesis of acetylenes. Catalytic substitutions of acetylenic hydrogen with bromo alkenes, iodo arenes, and bromopyridines", Tetrahedron Lett. 1975,50,4467.
17. Yi, C; Hua, R. "Efficient Copper-Free PdCl_2(PCy_3)_2-Catalyzed Sonogashira Coupling of ArylChlorides with Terminal Alkynes", J. Org. Chem. 2006, 71,2535.
18. Bennani, Y.; Anderson, J. T.; Wang, J.; Campbell, M. G. "Preparation of 4-piperidinol tertiary amines as histamine 3 receptor inhibitors for the treatment of obesity and others DNA disorders", WO2006071750 A1 (2006)
19. Shi, Z. F.; Wang, L. J.; Wang, H.; Cao, X. P.; Zhang, H. L. "Synthesis of Oligo(phenylene ethynylene)s with Dendrimer "Shells" for Molecular Electronics", Org. Lett. 2007, 9 (4), 595.
20. Percec, S.; Getty, R.; French, R. H.; Lustig, S. "Synthesis and characterization of substituted oligomers of phenylene ethynylenes", Polym. Prepr. (Am. Chem. Soc,Div. Polym. Chem.) 2004, 45 (2), 537.
21. Percec, S.; Getty, R.; Marshall, W.; Skidd, G.; French, R. "Synthesis, structural analysis, and self-assembly of phenylene ethynylene oligomers and their -F, -CF3,and -CH3 substituted derivatives", J. Polym. Sci., Part A: Polym. Chem. 2004, 42(3),541.
22. Wu, J.; Chi, C.; Wang, X.; Li, J.; Zhao, X.; Wang, F. "A one-pot procedure to prepare S-protected 4-iodothiophenols", Synth. Commun. 2000,30 (23), 4293.
23. Hsung, R. P.; Chidsey, C. E. D.; Sita, L. R. "Synthesis and Characterization of Unsymmetric Ferrocene-Terminated Phenylethynyl Oligomers Cp_2Fe-[C~0C-C_6H_4]n-X, (X = SH, SMe, SOMe, and SO2Me)", Organometallics 1995,14 (10), 4808.
24. Taher, D.; Walfort, B.; Lang, H. "Rigid-rod structured palladium complexes",Inorg. Chim. Acta 2006, 359 (6), 1899.
25. Hortholary, C.; Coudret, C. "An Approach to Long and Unsubstituted Molecular Wires: Synthesis of Redox-Active, Cationic Phenylethynyl Oligomers Designed for Self-Assembled Monolayers", J. Org. Chem. 2003, 68 (6), 2167.
26.Negishi, E.; Anastasia, L. "Palladium-Catalyzed Alkynylation", Chem. Rev. 2003,705(5), 1979.
27.Flatt, A. K.; Yao, Y.; Maya, F.; Tour, J. M. "Orthogonally Functionalized Oligomers for Controlled Self-Assembly",J. Org. Chem. 2004, 69, 1752.
28. Weber, H. B.; Reichert, J.; Weigend, F.; Ochs, R.; Beckmann, D.; Mayor, M.;Ahlrichs, R.; Lohneysen, H. V. "Electronic transport through single conjugated molecules", Chem. Phys. 2002,281,113.
29. Price, D. W.; Dirk, J. S. M.; Maya, F.; Tour, J. M. "Improved and new syntheses of potential molecular electronics devices", Tetrahedron 2003, 59,2497.