三联苯羧酸衍生物的合成与表征
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摘要
利用Ar-B(OH)2与烷氧基取代溴苯发生Suzuki反应,成功合成了含有柔性长链(-OC4H9,-OC8H17,-OC12H25,-OC14H29)的对羧基三联苯类电致发光材料中间体。此反应利用高效催化剂PdCl2-EDTA;在二氧六环／乙醇／水的均相体系中完成；得到了较高溶解性、发高效蓝色光的三联苯类荧光小分子。
用1H-NMR、FT-IR等确定了三联苯的结构,对其进行了荧光性、DSC检测。观察了三联苯的热稳定性能,对不同长度烷氧基链三联苯的发光效率进行了比较。得到了以下结论：
1.对Suzuki反应的路线和条件进行了优化。通过大量的实验探索从三条反应路线中找到了合成三联苯最合适的路线；通过对催化剂和溶剂的实验探索,发现使用PdCl2-EDTA作为催化剂和在二氧六环／乙醇／水的均相体系作为溶剂三联苯产率最高,反应时间较短且后处理简单。
2.通过DSC(结合TG图谱)可以看出这类化合物的热稳定性能比较好,分解温度在300℃以上。
3.通过荧光光谱图可以看出随着支链碳原子数的增加信号峰发生蓝移,发生蓝移是由于长的取代烷基链扭曲了三联苯的共轭平面,减弱了基于芳环的π电子体系,从而导致其发射波长的蓝移；而荧光强度是由链的长度而影响荧光自淬灭决定的。
A novel high solubility, violet or blue-light fluorescent triphenyl compounds containing a flexible long-chain(-OC4H9,-OC8H17,-OC12H25,-OC14H29)were synthesized for the first time in the dioxane-ethanol-water homogeneous system by Suzuki Reaction. It was prepared with p-boronobenzoic acid and alkoxy bromobenzene in the presence of PdCl2-EDTA.
Their chemical structures were confirmed by a variety of techniques including 1H NMR and FT-IR. The thermodynamic properties were investigated by the means of DSC. The optical properties were detected with UV and fluorescence spectra. The thermal stability and luminous efficiency of triphenyl derivatives with different alkoxy were investigated. Conclusions:
1.We optimized the synthetic route and reaction condition. Though a large number of experiments we find that with PdCl2-EDTA as a catalyst and dioxane/ethanol/water as the solvent reaction triple homogeneous system the highest yield of benzene, the reaction time shorter and simple treatment.
2.These compounds had relatively high thermal stability and decomposition temperature was above 300℃from DSC and TG spectrums.
3. With the increase of branched-chain carbon atoms the blue shift is enhanced from the fluorescence spectrum; the blue shift was caused by long alkyl chain distorting triphenyl conjugate plane, weaking theπelectronic system of aromatic ring, leading to blue shift; the fluorescence intensity is affected the fluorescence self-quenching.
用1H-NMR、FT-IR等确定了三联苯的结构,对其进行了荧光性、DSC检测。观察了三联苯的热稳定性能,对不同长度烷氧基链三联苯的发光效率进行了比较。得到了以下结论：
1.对Suzuki反应的路线和条件进行了优化。通过大量的实验探索从三条反应路线中找到了合成三联苯最合适的路线；通过对催化剂和溶剂的实验探索,发现使用PdCl2-EDTA作为催化剂和在二氧六环／乙醇／水的均相体系作为溶剂三联苯产率最高,反应时间较短且后处理简单。
2.通过DSC(结合TG图谱)可以看出这类化合物的热稳定性能比较好,分解温度在300℃以上。
3.通过荧光光谱图可以看出随着支链碳原子数的增加信号峰发生蓝移,发生蓝移是由于长的取代烷基链扭曲了三联苯的共轭平面,减弱了基于芳环的π电子体系,从而导致其发射波长的蓝移；而荧光强度是由链的长度而影响荧光自淬灭决定的。
A novel high solubility, violet or blue-light fluorescent triphenyl compounds containing a flexible long-chain(-OC4H9,-OC8H17,-OC12H25,-OC14H29)were synthesized for the first time in the dioxane-ethanol-water homogeneous system by Suzuki Reaction. It was prepared with p-boronobenzoic acid and alkoxy bromobenzene in the presence of PdCl2-EDTA.
Their chemical structures were confirmed by a variety of techniques including 1H NMR and FT-IR. The thermodynamic properties were investigated by the means of DSC. The optical properties were detected with UV and fluorescence spectra. The thermal stability and luminous efficiency of triphenyl derivatives with different alkoxy were investigated. Conclusions:
1.We optimized the synthetic route and reaction condition. Though a large number of experiments we find that with PdCl2-EDTA as a catalyst and dioxane/ethanol/water as the solvent reaction triple homogeneous system the highest yield of benzene, the reaction time shorter and simple treatment.
2.These compounds had relatively high thermal stability and decomposition temperature was above 300℃from DSC and TG spectrums.
3. With the increase of branched-chain carbon atoms the blue shift is enhanced from the fluorescence spectrum; the blue shift was caused by long alkyl chain distorting triphenyl conjugate plane, weaking theπelectronic system of aromatic ring, leading to blue shift; the fluorescence intensity is affected the fluorescence self-quenching.
引文
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[5]丁邦伟,吴书爱,许周利NONA的合成研究[J].火炸药,1995,3：17-18
[6]程格,王跃川.间三联苯类功能分子的合成及应用研究进展[J].化学通报,2002,65：1-6
[7]Kabalka G W, Wang L, Pagni R M, et al. Solbentless Suzuki coupling reaction on palladium-doped potassium fluoride alumina[J]. Synthesis,2003, (2):217-222
[8]张玉全,王进贤.微波辐射下钯催化偶联反应合成对三联苯[J].化学试剂,2005,27(1)：49-51
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[11]张蕾.[5C+lC(N)]环合反应构建三联苯及苯基联吡啶衍生物[D].东北师范大学,2009
[12]Chan S Oh. A simple and inexpensive synthetic method for alky, cyanobiphenyls[J]. Liq Cryst and Ordered Fluids,1978,3:532
[13]Dabrowaki, Roman. Liquid Crystalline P-cyano-p-allkylpolyphenyls[P]. Po 1:P1113437, 1982-04-30.
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[15]陈创前,蔡会武,杨鸿斌.4，4’-二碘-对-三联苯的合成研究[J].化工新型材料.2007.5135(5)：345-348
[16]徐玉文,林建明,李玲等.膨润土／丙烯酸／丙烯酰胺三元共聚物的合成与吸水性能研究[J].矿物学报,2006,26(2)：224-228.
[17]安忠维,陈新兵.4,4'-双烷基环己基三联苯液晶的合成[J].合成化学.2001.Vol9.No5
[18]谌烈,陈义旺,姚凯等.含氰基三联苯聚噻吩液晶共轭聚合物单体合成[J].工艺技术与材料.2009.05：24
[19]RADHAKRISHNAN S, SOMANATHAN N, NARASHIMHASWAMYT, et al. Thermal studies on polythiophene containing mesogenicside chains[J]. J Therm Anal Calor,2006,85(2):433-438
[20]GOTO H, AKAGI K, DAI X, et al. Synthesis and dielectricproperty of a ferroelectric liquid crystalline polythiophene derivative[J]. Ferroelectrics,2007,348(1):149-153
[21]许青青,李良超,叶芹萍.环上双氟取代三联苯类液晶化合物的量子化学研究[J].2005,35.(5)：617-629
[22]薛月霞,侯士法.4-羧基-对-三联苯的合成[J].精细化工.2002,35(5)：453-454
[23]Suzuki Yoshiichi,Hagivara Takashi, Kawamur Lchiro. Antiferroelectric liquid crystal compound[P]. EP:1995,2(8):624-637
[24]James David E. Method for monitoring the fluorescence of 4-carboxy-p-terphenyl in crude terephthalic acid[P]. US,1987,3(24):652-674
[25]Colonge J, Buendia J, Sabadie J. Synthese de derives substitues en 4 et-4,4"du paraterphenyle[J]. Bull Soc Chim Fr,1967,11:4370-4374
[26]Gilman H, Weipert E A. Some derivatives of p-terphenyl[J]. J Org. Chem.,1957,22:446-447
[27]Byron D J, Gray GW, Wilson R S. The synthesis of some substituted biphenyl-4-carboxylicAcids, 4-biphenylylacetic acids, and 4-aminobiphenyls[J]. J Chem. Soc.(C),1966,840-845
[28]黄步耕,何耀春,王江等.对-三联苯羧基化合成及其光谱特征[J].承德石油高等专科学校学报.2002,4(4)：127-131
[29]Campbell TW. Dicarboxylation of terpheny[J]. J. Am, Chem. Soc.,1960,82:3126-3128
[30]董兆恒,王建文,高仁孝等Suzuki偶联反应合成三联苯中的副产物研究.合成化学[J].2007,5(6)：731-734
[31]黄锡珉.显示技术新进展[J].液晶与显示,2000,15(1)：1-5
[32]赵敏,蒯乃功.多环苯基环己烷类液晶的合成[J].华东理工大学学报,1996,22(2)：217-220
[33]龙志庭.对三联苯类化合物紫外吸收光谱性能的研究[J].染料工业.1994.31(5).37-48
[34]龙志庭.对三联苯类化合物荧光光谱性能的研究[J].染料工业.1995.32(2).64-66
[35]Guo,G., Zhang,Y., Liu,H., Xie,P. and Zhang,R.B. [J], Macromol. Rapid Comm.,2002,23:366
[36]Zhang,T. Y., Deng, K., Zhang,p., Xie, P. and Zhang R. B[J]., Chem. Eur. j.,2006,12:3630
[37]Miyaura, N.; Suzuki[J], A. Chem. Rev.1995,95:2457-2483
[38]Miyaura N, Yanagi T,Suzuki A. The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases[J]. Synth Commun,1981,11 (7):513-519.
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