含苯氧基、联萘氧基、偶氮苯氧基均三嗪衍生物的制备与表征
|
摘要
本文以三聚氯氰作为提供均三嗪环的主要原料,利用其结构中的三个氯原子参与反应时的不同反应活性,可以控制条件分步进行的特点,制备了一系列新型含均三嗪环化合物,采用元素分析、红外光谱、核磁共振等研究方法对它们的结构进行表征,并研究了其溶解性,热稳定性等性能。具体包括以下内容：
1.以三聚氯氰和对硝基苯酚为原料,控制反应温度,采用丙酮水法制备了2,4,6-三(4-硝基苯氧基)-1,3,5-均三嗪。采用三种不同的还原方法对硝基进行还原,制得2,4,6-三(4-氨基苯氧基)-1,3,5-均三嗪。应用元素分析,1H-NMR, IR对所得的产品进行表征。其中2,4,6-三(4-硝基苯氧基)-1,3,5-均三嗪具有很好的热稳定性,初始分解温度为430℃。所选择的三种还原方法中以Pd/C水合肼催化体系的还原效果最好。
2.以三聚氯氰和1,1’-联二萘酚为原料,NaOH为缚酸剂,十六烷基三甲基溴化铵为相转移催化剂,界面缩聚制备聚2-氯-4-1,1’-联萘氧基-1,3,5-均三嗪。采用紫外,荧光,IR, 1H-NMR, GPC等对聚合物进行表征；同时通过TG,DSC研究了该聚合物的热性能；通过原子力显微镜观察该聚合物薄膜微观形态。结果表明,此聚合物的二氯甲烷溶液能在玻璃片上成膜,且出现纳米级孔洞。
3.以三聚氯氰和4,4-二羟基偶氮苯为原料,NaOH为缚酸剂,十六烷基三甲基溴化铵为相转移催化剂,界面缩聚制备聚2-氯-4,4,4’-偶氮苯氧基-1,3,5-均三嗪(PCCAB)。以NaOH为缚酸剂,在丙酮水溶液中将4,4’-二羟基偶氮苯和2-苯胺基-4,6-二氯-1,3,5-均三嗪反应制备了4,4’-二(间苯胺基一氯三嗪基)羟基偶氮苯(DIATOB)。通过红外、核磁、紫外对其结构进行表征。通过TG对产品进行热性能分析；通过紫外光谱测试了DIATOB的光响应性能；同时观察了两者的溶解性,通过比较结果表明,PCCAB即使在DMF中也不溶解,而DIATOB则可溶于多数常用溶剂。
In this paper, cyanuric chloride which structure containing three chlorine atoms was used as the main raw material for the provision of s-triazine ring.With the different reactivities of the three chlorine atoms in cyanuric chloride, a series of new s-triazine ring compounds were received by the step-wise reaction through the controlling of the temperature.The structure of these compounds were characterized by Elemental analysis, IR,1H NMR and other research methods,also the solubility, thermal stability properties were studied. It can be summarized as follows.
1. With cyanuric chloride and p-nitrophenol as the raw materials,2,4,6-3-p-nitrophenoxy-1,3,5-triazine was prepared by controlling of reaction temperature in acetone and water. Three different methods were used for nitro reduction to obtain 2,4,6--aminophenoxy-1,3,5-triazine. With elemental analysis,1H-NMR, IR,TG characterization the products obtained,2,4,6-3-p-nitrophenoxy-1,3,5-triazine shows good thermal stability which the initial decomposition temperature was at 430℃. Pd/C hydrazine catalyst system shows a good result in three kinds of reduction methods.
2. With cyanuric chloride and 1,1'-BINOL as the raw materials, NaOH as base, cetyltrimethyl ammonium bromide as phase transfer catalyst, poly 2-chloro-4-1,1'-bi naphthyloxy-1,3,5-triazine were prepared through interfacial polymerization. Its structure was characterized using UV, IR,1H-NMR, RF, GPC. Also by atomic force microscope(AFM), the surface of the polymer film was observed.
3. PCCAB was abtained by the reaction of cyanuric chloride and 4,4'-hydroxyazobenzene using interfacial polymerization. DIATOB was got by the reaction of 2-Anilino-4,6-dicholoride-1,3,5-traizine and 4,4'-hydroxyazobenzene at 40℃in the solvent of acetone and water. FTIR,1HNMR, TG, DSC, UV were used to characterize the structures. And the opticl response property of DIATOB was studied by UV-Vis. Also the solubility of the two products were studied, PCCAB won't dissolve even in DMF, but DIATOB can be dissolved in most kinds of solvent.
1.以三聚氯氰和对硝基苯酚为原料,控制反应温度,采用丙酮水法制备了2,4,6-三(4-硝基苯氧基)-1,3,5-均三嗪。采用三种不同的还原方法对硝基进行还原,制得2,4,6-三(4-氨基苯氧基)-1,3,5-均三嗪。应用元素分析,1H-NMR, IR对所得的产品进行表征。其中2,4,6-三(4-硝基苯氧基)-1,3,5-均三嗪具有很好的热稳定性,初始分解温度为430℃。所选择的三种还原方法中以Pd/C水合肼催化体系的还原效果最好。
2.以三聚氯氰和1,1’-联二萘酚为原料,NaOH为缚酸剂,十六烷基三甲基溴化铵为相转移催化剂,界面缩聚制备聚2-氯-4-1,1’-联萘氧基-1,3,5-均三嗪。采用紫外,荧光,IR, 1H-NMR, GPC等对聚合物进行表征；同时通过TG,DSC研究了该聚合物的热性能；通过原子力显微镜观察该聚合物薄膜微观形态。结果表明,此聚合物的二氯甲烷溶液能在玻璃片上成膜,且出现纳米级孔洞。
3.以三聚氯氰和4,4-二羟基偶氮苯为原料,NaOH为缚酸剂,十六烷基三甲基溴化铵为相转移催化剂,界面缩聚制备聚2-氯-4,4,4’-偶氮苯氧基-1,3,5-均三嗪(PCCAB)。以NaOH为缚酸剂,在丙酮水溶液中将4,4’-二羟基偶氮苯和2-苯胺基-4,6-二氯-1,3,5-均三嗪反应制备了4,4’-二(间苯胺基一氯三嗪基)羟基偶氮苯(DIATOB)。通过红外、核磁、紫外对其结构进行表征。通过TG对产品进行热性能分析；通过紫外光谱测试了DIATOB的光响应性能；同时观察了两者的溶解性,通过比较结果表明,PCCAB即使在DMF中也不溶解,而DIATOB则可溶于多数常用溶剂。
In this paper, cyanuric chloride which structure containing three chlorine atoms was used as the main raw material for the provision of s-triazine ring.With the different reactivities of the three chlorine atoms in cyanuric chloride, a series of new s-triazine ring compounds were received by the step-wise reaction through the controlling of the temperature.The structure of these compounds were characterized by Elemental analysis, IR,1H NMR and other research methods,also the solubility, thermal stability properties were studied. It can be summarized as follows.
1. With cyanuric chloride and p-nitrophenol as the raw materials,2,4,6-3-p-nitrophenoxy-1,3,5-triazine was prepared by controlling of reaction temperature in acetone and water. Three different methods were used for nitro reduction to obtain 2,4,6--aminophenoxy-1,3,5-triazine. With elemental analysis,1H-NMR, IR,TG characterization the products obtained,2,4,6-3-p-nitrophenoxy-1,3,5-triazine shows good thermal stability which the initial decomposition temperature was at 430℃. Pd/C hydrazine catalyst system shows a good result in three kinds of reduction methods.
2. With cyanuric chloride and 1,1'-BINOL as the raw materials, NaOH as base, cetyltrimethyl ammonium bromide as phase transfer catalyst, poly 2-chloro-4-1,1'-bi naphthyloxy-1,3,5-triazine were prepared through interfacial polymerization. Its structure was characterized using UV, IR,1H-NMR, RF, GPC. Also by atomic force microscope(AFM), the surface of the polymer film was observed.
3. PCCAB was abtained by the reaction of cyanuric chloride and 4,4'-hydroxyazobenzene using interfacial polymerization. DIATOB was got by the reaction of 2-Anilino-4,6-dicholoride-1,3,5-traizine and 4,4'-hydroxyazobenzene at 40℃in the solvent of acetone and water. FTIR,1HNMR, TG, DSC, UV were used to characterize the structures. And the opticl response property of DIATOB was studied by UV-Vis. Also the solubility of the two products were studied, PCCAB won't dissolve even in DMF, but DIATOB can be dissolved in most kinds of solvent.
引文
[1]Blotny G.. Recent applications of 2,4,6-trichloro-1,3,5-triazine and its derivatives in organic synthesis[J]. Tetrahedron,2006,62,9507-9522.
[2]Cevdet U, Mesude I., Ayse E, et al.The bioaccumulation of nonylphenol and its adverse efect on the liver of rainbow trout[J]. Environ res,2003,92:262-270.
[3]马会民,苏美红,梁树权.三嗪类光学探针与标记分析[J].分析化学,2003,1256-1260
[4]聂丽华,马会民,李晓花,等.通过荧光三嗪探针的多氢作用识别胸腺嘧啶[J].高等学校化学学报,2003,24,37-39.
[5]魏薇,王洪鉴,江崇球,等.新型荧光试剂1,5-二(4,6-二氯三嗪)-氨基萘与酪氨酸相互作用[J].分析化学,2007,1772-1775.
[6]Gustafson G R., Baldino C M, O'Donnell M M, et al. Incorporation of carbohydrates and peptides into large triazine-based screening libraries using automated parallel synthesis[J]. Tetrahedron 1998,54,4051-4065.
[7]肖深初,郑良彬,谢文忠,等.meso-三嗪取代苯基卟啉的简单一锅合成[J].高等学校化学学报,2009,30,479-482.
[8]Zerkowski J A, Hensley L M, Abramowitz D. Triazinyl-Amino Acids, New Building Blocks for Pseudopeptides[J]. Synlett,2002,557-560.
[9]Guo Q,Xie Y,Wang X,et al. Synthesis of carbon nitride nanotubes with the C3N4 stoichiometry via a benzene-thermal process at low temperatures[J].Chem.Commun., 2004,26-27.
[10]Wang M X, Yang H B. A General and High Yielding Fragment Coupling Synthesis of Heteroatom-Bridged Calixarenes and the Unprecedented Examples of Calixarene Cavity Fine-Tuned by Bridging Heteroatoms[J]. J. Am. Chem. Soc.,2004, 126,15412-15422.
[11]Lowik D W P M, Lowe C R. Synthesis of macrocyclic, triazine-based receptor molecules[J].Eur. J. Org. Chem.,2001,2825-2839.
[12]杨贵宝.三聚氯氰与脂肪族多胺的反应研究及树枝状多臂引发核的制备[D]苏州大学,2009,1.
[13]Zhang W, Simanek E E. Dendrimers Based on Melamine. Divergent and Orthogonal, Convergent Syntheses of a G3 Dendrimer[J].Org. Lett.,2000,2,843-845.
[14]Zhang W, Nowlan D T, Thomson L M, et al. Orthogonal, Convergent Syntheses of Dendrimers Based on Melamine with One or Two Unique Surface Sites for Manipulation[J]. J. Am. Chem. Soc.,2001,123,8914-8922.
[15]Zhang W, Simanek E E. Synthesis and characterization of higher generation dendrons based on melamine using p-aminobenzylamine. Evidence for molecular recognition of Cu(Ⅱ) [J]. Tetrahedron Lett.,2001,42,5355-5357.
[16]Zhang W, Tichy S E, Perez L M,et al. Evaluation of Multivalent Dendrimers Based on Melamine:Kinetics of Thiol-Disulfide Exchange Depends on the Structure of the Dendrimer[J]. J. Am. Chem. Soc.,2003,125,5086-5094.
[17]Steffensen M, Simanek E E. Synthesis and Manipulation of Orthogonally Protected Dendrimers:Building Blocks for Library Synthesis [J].Angew. Chem., Int. Ed. 2004,43,5178-5180.
[18]Chen H T, Neerman M F, Parrish A R, et al.Cytotoxicity, Hemolysis, and Acute in Vivo Toxicity of Dendrimers Based on Melamine, Candidate Vehicles for Drug Delivery[J]. J. Am. Chem. Soc.,2004,126,10044-10048.
[19]Steffensen M B,Simanek E E. Chemoselective building blocks for dendrimers from relative reactivity data[J]. Org. Lett.,2003,5,2359-2361.
[20]Lai L L, Wang L Y, Lee C H, et al. Nanomaterials of triazine-based dendrons: convergent synthesis and their physical studies[J]. Org. Lett.,2006,8,1541-1544.
[21]Lehn J M, Mascal M, DeCian A,et al. Molecular Recognition directed Self-assembly of Ordered Supramolecular Strands by Cocrystallization of Complementary Molecular Components[J]. J. Chem. Soc.,Chem Commun,1990,479-480
[22]Mathias J P, Seto C T, Simanek E E, et al. Self-Assembly through Hydrogen Bonding: Preparation and Characterization of Three New Types of Supramolecular Aggregates Based on Parallel Cyclic CA3.cntdot.M3 "Rosettes"[J]. J. Am. Chem. Soc.,1994,116, 1725-1736.
[23]Masala S, Tadei M. Solid-Supported Chloro[1,3,5]triazine. A Versatile New Synthetic Auxiliary for the Synthesis of Amide Libraries [J].Org. Lett.,1999,1,1355-1357.
[24]Ditzler M A, Doherty G, Sieber S, et al. Fluorescence study of an immobilized ligand--metal ion complex[J].Anal. Chim. Acta,1982,142:305-311
[25]Ching-Erh Lin, Fang-Kuo Li, Chen-Hsing Lin. Evaluation of new chiral stationary phases of bonded cyanuric chloride with amino acid and naphthylalkylamine substituents for liquid chromatographic separation of amino acids and amino alcohols as dinitrobenzoyl derivatives[J]. Journal of Chromatography A,1996,722,211-220
[26]Falchi A,Tadei M. PEG-dichlorotriazine (PEG-DCT):A New Soluble Polymer-Supported Scavenger for Alcohols, Thiols, Phosphines, and Phosphine Oxides[J]. Org. Lett.,2000,2,3429-3431.
[27]Marsh A, Carlisle S J, Smith S C. High-loading scavenger resins for combinatorial chemistry[J]. Tetrahedron Lett.,2001,42,493-496.
[28]Mallakpour S, Rafiemanzelat F. Synthesis and characterization of new optically active poly(amide-imide-urethane)thermoplastic elastomers, derived from bis(p-amido benzoic acid)-N-trimellitylimido-l-leucine and polyoxyethylene-MDI[J]. Reactive & Functional Polymers,2005,62(2):153-167.
[29]洪哲.旋光性聚合物研究进展[J].延边大学学报,2001,27(2)：139-143.
[30]黄梅芳,刘朋生.旋光性高分子的合成研究之进展[J].湘潭大学社会科学学报,2002,26：197-198.
[31]刘引烽,华家栋.旋光性高分子的合成(上)[J].高分子通报,1994,6(2)：72-79：
[32]刘引烽,华家栋.旋光性高分子的合成(下)[J].高分子通报,1994,9(3)：136-173.
[33]洪哲,欧英富,张宏莉.旋光性聚合物的合成进展[J].丹东纺专学报,2001,8(1)：3-7.
[34]刘引烽,张荣群,章科健,等.旋光高分子的旋光能力(上)[J].高分子通报,1995,9(3)：159-162.
[35]Man K N, Hak F C, Tze L C, et al. Synthesis and chiroptical properties of axially chiral, Binaphthol-based oligomers [J]. Tetrahedron Letters,1996,37(7):2979-2982.
[36]宋乃恒,高连勋,邱雪鹏,等.含1,1'-联萘基团可溶性聚酯酰亚胺的合成与性质[J].应用化学,1999,16(5)：13-16.
[37]侯士法,姜劲越,丁孟贤,等.含联萘基团的旋光性聚喹啉的合成与性质[J].高等学校化学学报,2002,23(3)：486-489.
[38]卞证,何亚兵,高连勋.一种新型联萘基旋光共轭聚合物的圆二色谱和圆偏振荧光光谱[J].高等学校化学学报,2003,24(3)：559-561.
[39]Yu H B, Hu Q S, Pu L. Synthesis of a rigid and optically active poly(BINAP)and its application in asymmetric catalysis[J]. Tetrahedron Letters,2000,41:1681-1685
[40]Lee Y K, Nakashima Y, Onimura K, et al. Free-radical polymerization of(R)-(-)-1-(1-naphthyl) ethyl(2-methacryloyloxyethyl)urea and chiral recognitionability[J]. Macromolecules,2003,36:4735-4742.
[41]南秋利,周钰民,陈景,等.新型含联萘基团的旋光聚氨酯的制备与性能表征[J].高等学校化学学报,2007,28,1393-1397
[42]Mikami K, Matsumoto Y, Xu L. Modification of alkoxo ligands of BINOL Ti ladder: Isolation and X-ray crystallographic analysis[J]. Inorganica Chimica Acta,2006, 359(13):4159-4167.
[43]Burehell T J, Eisler D J, Puddephatt R J. Polymeric silver(Ⅰ)and mercury(Ⅱ) complexes with chiral bis(pyridyl)ligands[J]. Jourflal of Molecular Structure,2006, 796:47-57.
[44]Gong Y Q, Zhou Y F, Han L, et al. Two new polymeric chains derived from exo-bidentate binaphthol derivatives[J]. Journal of Molecular Structure,2005, 748(1-3):195-199.
[45]范青华,杨夕强,刘国华,等.新型树状结构手性联二萘酚衍生物的合成及催化性能研究[J].高等学校化学学报,2003,24(2)：274-277.
[46]Song J F, Chang Y X, Chen L W, et al. Synthesis and characterization of polybinaphthalene incorporating chiral(R)or(S)-1,1 prime binaphthalene and oxadiazole units by Heck reaction[J]. European Polymer Journal,2006,42(3): 663-669.
[47]陈令武,成义祥,宋金峰,等.含(R)或(s)-1,1'-联萘和噁二唑单元的手性高分子合成与性质研究[J].高等学校化学学报,2005,26(9)：1747-1751.
[48]余虹,赵元聪,余孝其.联二萘酚咪唑鎓盐二聚体的合成[J].化学研究与应用,2006,18(10)：1235-1237.
[49]Pu L. 1,1'-Binaphthyl dimers, oligomers and polymers:Molecular recognition, asymmetric catalysis andnew materials [M]. Chem.Rev.,1998,98:2405-2494.
[50]Korihara S, Sakamoto A, Yoneyama D. Photochemical Switching Behavior of Liquid Crystalline Polymer Networks Containing Azobenzene Molecules[J]. Macromolecules, 1999,32,6493-6498.
[51]Luo W, She S. Improvement of all-optical switching efect based on azobenzene-containing polymer films[J]. Appl. Phys.B,2005,80,77-80.
[52]Wang H,Huang Y,Liu Z. Ultrafast photoinduced anisotropy and optical switching in azobenzene sidechain polymers[J]. Appl. Phys. Lett.,2803,82,3394-3396.
[53]Shi Y, Olson D J, Bechtel J H. Photoinduced molecular alignment relaxation in poled electro-optic polymer thin films[J]. Appl. Phys. Lett.,1996,68(8),1040-1042.
[54]Barret C, Choudhury B, Natansohn A. Azoearbazole Polymethacrylates as Single-Component Electrooptic Materials[J]. Macromolecules,1998,31,4845-4851.
[55]Iftime G, Labarthet F L, Natansohn A. Main Chain-Containing Azo-Tetraphenyl diamino biphenyl Photorefractive Polymers[J]. Chem. Mater.,2002,14:168-174.
[56]Ducharme S, Scot J C, Twing R J. Observation of the photorefractive elect in a polymer[J]. Phys Rev Lett,1991,66:1864-1872.
[57]Hvilsted S, Andrazzi F, Kulina C. Novel Side-Chain Liquid Crystalline Polyester Architecture for Reversible Optical Storage[J]. Macromolecules,1995,28: 2172-2179.
[58]Todorov T, Nikolova L, Tomova N. Polarization holography I:A new high-eficiency organic material with reversible photoindueed bbeffingence[J]. Appl. Opt.,1984,23: 4309-4313.
[59]傅正生,王长青,薛华丽,等.含偶氮苯光学活性侧基聚合物研究进展[J].高分子通报,2004,4,10-11
[60]车鹏超,和亚宁,王晓工.重氮偶合方法合成主链型光响应偶氮聚合物[J].高分子学报,2006,8,977-981.
[61]王瑞东,王晓工.一种主侧链均含偶氮基团的聚合物合成与研究[J].中国科技论文在线,2009,413-417.
[62]江兆建,游毅.含偶氮苯基团的阳离子表面活性剂的合成[J].合成化学,2009,246-248.
[63]宋冰蕾,赵剑曦.光敏季铵盐Gemini表面活性剂a4-6-m在气/液界面的吸附[J].物理化学学报,2009,25(10)：2020-202.
[64]Hassan N, Mohsen A. Synthesis of barbell-like triblock copolymers, dendritic triazine-block-poly(ethylene glycol)-block-dendritic triazine and investigation of their solution behaviors[J]. Polymer,2005,10788-10799.
[65]Lee C-H, Yamamoto T. Synthesis and characterization of a new class of liquid-crystalline, highly luminescent molecules containing a 2,4,6-triphenyl-1,3,5-triazine unit[J]. Tetrahedron Lett,2001,42:3993.
[66]Lupton J M, Hemingway L R, Samuel, etal. Electroluminescence from a new distyrylbenzene based triazine dendrimer[J]. J.Mater.Chem.,2000,10:867.
[67]罗春华,于美娜,赵凌,等.固态反应合成2,4,6-三苯氧基均三嗪-1,3,5-均三嗪衍生物[J].应用化学,2005,22：811.
[68]Takagi K, Hattori T, Kunisada H, et al. Triazine Dendrimers by Divergent and Convergent Methods[J]. Journal of Polymer Science:Part A:Polymer Chemistry, 2000,38:4385-4395.
[69]Anastasios P M, John A M. New crosslinkable polyimides,polyamides and polyureas derived from 2,4,6-tris(4-aminophenoxy)-s-triazine[J]. Eur.Polym.J.,1989,25: 455-460.
[70]吕荣文,张竹霞,高昆玉.芳硝基物的水合肼催化还原研究进展[J].染料与染色,2003,40：160-162.
[71]Schaefer F C, Thurston J T, Dudley J R. Cyanuric chloride derivatives.Ⅳ.Aryloxy-s-triazines[J]. J Am Chem Soc,1951,73:2900.
[72]杨进,刘习奎,汤嘉陵,等.3,5-二氨基苯甲酸-4'-联苯酯的合成[J].四川大学学报,2004,36：53-56.
[73]邢其毅,徐瑞秋,周政,等,基础有机化学[M].第二版.北京：高等教育出版社,1994.
[74]Allen G, De Boos A.G Preparation and properties of the poly(2-chlorocyanurate) of bisphenol A[J]. Polymer,1974,56-59.
[75]U. H. F. Bunz. Breath Figures as a Dynamic Templating Method for Polymers and Nanomaterials[J]. Adv. Mater.2006,18,973-989
[76]O. Pitois, B. Francois. Formation of ordered micro-porous membrance. Eur. Phys. J. B [J],1999,8,225-231
[77]何本桥,李建新,边栋材,有序多孔膜表面微球图案化[J].功能材料,2009,40,1379-1380,1384
[78]徐艳莲,林金火,胡炳环,漆酚醛胺聚合物多孔膜的制备[J].高分子学 报,2008,5,497-499
[79]Cha S W, Choi S H, Jin J I, et al. Synthesis and luminescence properties of four armed conjugated structures containing 1,3,4oxadiazole moieties[J]. J. Mater. Chem., 2003,13,1900-1904.
[80]Bredas J L, Adant C, Tackx P, et al. Third-order nonlinear optical response in organic materials:theoretical and experimental aspects[J]. Chem.Rev.,1994,94:243-278.
[81]Wang Wenjun, Wu Cheng, Gao Xuexi, et al. Studies on spectra and nonlinear optical properties of NMOB in langmuirblodgett films[J]. Chin. J. Lasers(中国激光),2005, 32:1123-1126(in Chinese).
[82]Zhao D X, Andreazza C, Andreazza P, et al. Bufer layer efect on ZnO nanorods growth alignment[J]. Chem Pbys Lett,2005,408:335—338.
[83]刘艳凤,花成文,苟小锋,等.三嗪类氮杂环蕃的合成与表征[J].有机化学,2009,1419-1422.
[2]Cevdet U, Mesude I., Ayse E, et al.The bioaccumulation of nonylphenol and its adverse efect on the liver of rainbow trout[J]. Environ res,2003,92:262-270.
[3]马会民,苏美红,梁树权.三嗪类光学探针与标记分析[J].分析化学,2003,1256-1260
[4]聂丽华,马会民,李晓花,等.通过荧光三嗪探针的多氢作用识别胸腺嘧啶[J].高等学校化学学报,2003,24,37-39.
[5]魏薇,王洪鉴,江崇球,等.新型荧光试剂1,5-二(4,6-二氯三嗪)-氨基萘与酪氨酸相互作用[J].分析化学,2007,1772-1775.
[6]Gustafson G R., Baldino C M, O'Donnell M M, et al. Incorporation of carbohydrates and peptides into large triazine-based screening libraries using automated parallel synthesis[J]. Tetrahedron 1998,54,4051-4065.
[7]肖深初,郑良彬,谢文忠,等.meso-三嗪取代苯基卟啉的简单一锅合成[J].高等学校化学学报,2009,30,479-482.
[8]Zerkowski J A, Hensley L M, Abramowitz D. Triazinyl-Amino Acids, New Building Blocks for Pseudopeptides[J]. Synlett,2002,557-560.
[9]Guo Q,Xie Y,Wang X,et al. Synthesis of carbon nitride nanotubes with the C3N4 stoichiometry via a benzene-thermal process at low temperatures[J].Chem.Commun., 2004,26-27.
[10]Wang M X, Yang H B. A General and High Yielding Fragment Coupling Synthesis of Heteroatom-Bridged Calixarenes and the Unprecedented Examples of Calixarene Cavity Fine-Tuned by Bridging Heteroatoms[J]. J. Am. Chem. Soc.,2004, 126,15412-15422.
[11]Lowik D W P M, Lowe C R. Synthesis of macrocyclic, triazine-based receptor molecules[J].Eur. J. Org. Chem.,2001,2825-2839.
[12]杨贵宝.三聚氯氰与脂肪族多胺的反应研究及树枝状多臂引发核的制备[D]苏州大学,2009,1.
[13]Zhang W, Simanek E E. Dendrimers Based on Melamine. Divergent and Orthogonal, Convergent Syntheses of a G3 Dendrimer[J].Org. Lett.,2000,2,843-845.
[14]Zhang W, Nowlan D T, Thomson L M, et al. Orthogonal, Convergent Syntheses of Dendrimers Based on Melamine with One or Two Unique Surface Sites for Manipulation[J]. J. Am. Chem. Soc.,2001,123,8914-8922.
[15]Zhang W, Simanek E E. Synthesis and characterization of higher generation dendrons based on melamine using p-aminobenzylamine. Evidence for molecular recognition of Cu(Ⅱ) [J]. Tetrahedron Lett.,2001,42,5355-5357.
[16]Zhang W, Tichy S E, Perez L M,et al. Evaluation of Multivalent Dendrimers Based on Melamine:Kinetics of Thiol-Disulfide Exchange Depends on the Structure of the Dendrimer[J]. J. Am. Chem. Soc.,2003,125,5086-5094.
[17]Steffensen M, Simanek E E. Synthesis and Manipulation of Orthogonally Protected Dendrimers:Building Blocks for Library Synthesis [J].Angew. Chem., Int. Ed. 2004,43,5178-5180.
[18]Chen H T, Neerman M F, Parrish A R, et al.Cytotoxicity, Hemolysis, and Acute in Vivo Toxicity of Dendrimers Based on Melamine, Candidate Vehicles for Drug Delivery[J]. J. Am. Chem. Soc.,2004,126,10044-10048.
[19]Steffensen M B,Simanek E E. Chemoselective building blocks for dendrimers from relative reactivity data[J]. Org. Lett.,2003,5,2359-2361.
[20]Lai L L, Wang L Y, Lee C H, et al. Nanomaterials of triazine-based dendrons: convergent synthesis and their physical studies[J]. Org. Lett.,2006,8,1541-1544.
[21]Lehn J M, Mascal M, DeCian A,et al. Molecular Recognition directed Self-assembly of Ordered Supramolecular Strands by Cocrystallization of Complementary Molecular Components[J]. J. Chem. Soc.,Chem Commun,1990,479-480
[22]Mathias J P, Seto C T, Simanek E E, et al. Self-Assembly through Hydrogen Bonding: Preparation and Characterization of Three New Types of Supramolecular Aggregates Based on Parallel Cyclic CA3.cntdot.M3 "Rosettes"[J]. J. Am. Chem. Soc.,1994,116, 1725-1736.
[23]Masala S, Tadei M. Solid-Supported Chloro[1,3,5]triazine. A Versatile New Synthetic Auxiliary for the Synthesis of Amide Libraries [J].Org. Lett.,1999,1,1355-1357.
[24]Ditzler M A, Doherty G, Sieber S, et al. Fluorescence study of an immobilized ligand--metal ion complex[J].Anal. Chim. Acta,1982,142:305-311
[25]Ching-Erh Lin, Fang-Kuo Li, Chen-Hsing Lin. Evaluation of new chiral stationary phases of bonded cyanuric chloride with amino acid and naphthylalkylamine substituents for liquid chromatographic separation of amino acids and amino alcohols as dinitrobenzoyl derivatives[J]. Journal of Chromatography A,1996,722,211-220
[26]Falchi A,Tadei M. PEG-dichlorotriazine (PEG-DCT):A New Soluble Polymer-Supported Scavenger for Alcohols, Thiols, Phosphines, and Phosphine Oxides[J]. Org. Lett.,2000,2,3429-3431.
[27]Marsh A, Carlisle S J, Smith S C. High-loading scavenger resins for combinatorial chemistry[J]. Tetrahedron Lett.,2001,42,493-496.
[28]Mallakpour S, Rafiemanzelat F. Synthesis and characterization of new optically active poly(amide-imide-urethane)thermoplastic elastomers, derived from bis(p-amido benzoic acid)-N-trimellitylimido-l-leucine and polyoxyethylene-MDI[J]. Reactive & Functional Polymers,2005,62(2):153-167.
[29]洪哲.旋光性聚合物研究进展[J].延边大学学报,2001,27(2)：139-143.
[30]黄梅芳,刘朋生.旋光性高分子的合成研究之进展[J].湘潭大学社会科学学报,2002,26：197-198.
[31]刘引烽,华家栋.旋光性高分子的合成(上)[J].高分子通报,1994,6(2)：72-79：
[32]刘引烽,华家栋.旋光性高分子的合成(下)[J].高分子通报,1994,9(3)：136-173.
[33]洪哲,欧英富,张宏莉.旋光性聚合物的合成进展[J].丹东纺专学报,2001,8(1)：3-7.
[34]刘引烽,张荣群,章科健,等.旋光高分子的旋光能力(上)[J].高分子通报,1995,9(3)：159-162.
[35]Man K N, Hak F C, Tze L C, et al. Synthesis and chiroptical properties of axially chiral, Binaphthol-based oligomers [J]. Tetrahedron Letters,1996,37(7):2979-2982.
[36]宋乃恒,高连勋,邱雪鹏,等.含1,1'-联萘基团可溶性聚酯酰亚胺的合成与性质[J].应用化学,1999,16(5)：13-16.
[37]侯士法,姜劲越,丁孟贤,等.含联萘基团的旋光性聚喹啉的合成与性质[J].高等学校化学学报,2002,23(3)：486-489.
[38]卞证,何亚兵,高连勋.一种新型联萘基旋光共轭聚合物的圆二色谱和圆偏振荧光光谱[J].高等学校化学学报,2003,24(3)：559-561.
[39]Yu H B, Hu Q S, Pu L. Synthesis of a rigid and optically active poly(BINAP)and its application in asymmetric catalysis[J]. Tetrahedron Letters,2000,41:1681-1685
[40]Lee Y K, Nakashima Y, Onimura K, et al. Free-radical polymerization of(R)-(-)-1-(1-naphthyl) ethyl(2-methacryloyloxyethyl)urea and chiral recognitionability[J]. Macromolecules,2003,36:4735-4742.
[41]南秋利,周钰民,陈景,等.新型含联萘基团的旋光聚氨酯的制备与性能表征[J].高等学校化学学报,2007,28,1393-1397
[42]Mikami K, Matsumoto Y, Xu L. Modification of alkoxo ligands of BINOL Ti ladder: Isolation and X-ray crystallographic analysis[J]. Inorganica Chimica Acta,2006, 359(13):4159-4167.
[43]Burehell T J, Eisler D J, Puddephatt R J. Polymeric silver(Ⅰ)and mercury(Ⅱ) complexes with chiral bis(pyridyl)ligands[J]. Jourflal of Molecular Structure,2006, 796:47-57.
[44]Gong Y Q, Zhou Y F, Han L, et al. Two new polymeric chains derived from exo-bidentate binaphthol derivatives[J]. Journal of Molecular Structure,2005, 748(1-3):195-199.
[45]范青华,杨夕强,刘国华,等.新型树状结构手性联二萘酚衍生物的合成及催化性能研究[J].高等学校化学学报,2003,24(2)：274-277.
[46]Song J F, Chang Y X, Chen L W, et al. Synthesis and characterization of polybinaphthalene incorporating chiral(R)or(S)-1,1 prime binaphthalene and oxadiazole units by Heck reaction[J]. European Polymer Journal,2006,42(3): 663-669.
[47]陈令武,成义祥,宋金峰,等.含(R)或(s)-1,1'-联萘和噁二唑单元的手性高分子合成与性质研究[J].高等学校化学学报,2005,26(9)：1747-1751.
[48]余虹,赵元聪,余孝其.联二萘酚咪唑鎓盐二聚体的合成[J].化学研究与应用,2006,18(10)：1235-1237.
[49]Pu L. 1,1'-Binaphthyl dimers, oligomers and polymers:Molecular recognition, asymmetric catalysis andnew materials [M]. Chem.Rev.,1998,98:2405-2494.
[50]Korihara S, Sakamoto A, Yoneyama D. Photochemical Switching Behavior of Liquid Crystalline Polymer Networks Containing Azobenzene Molecules[J]. Macromolecules, 1999,32,6493-6498.
[51]Luo W, She S. Improvement of all-optical switching efect based on azobenzene-containing polymer films[J]. Appl. Phys.B,2005,80,77-80.
[52]Wang H,Huang Y,Liu Z. Ultrafast photoinduced anisotropy and optical switching in azobenzene sidechain polymers[J]. Appl. Phys. Lett.,2803,82,3394-3396.
[53]Shi Y, Olson D J, Bechtel J H. Photoinduced molecular alignment relaxation in poled electro-optic polymer thin films[J]. Appl. Phys. Lett.,1996,68(8),1040-1042.
[54]Barret C, Choudhury B, Natansohn A. Azoearbazole Polymethacrylates as Single-Component Electrooptic Materials[J]. Macromolecules,1998,31,4845-4851.
[55]Iftime G, Labarthet F L, Natansohn A. Main Chain-Containing Azo-Tetraphenyl diamino biphenyl Photorefractive Polymers[J]. Chem. Mater.,2002,14:168-174.
[56]Ducharme S, Scot J C, Twing R J. Observation of the photorefractive elect in a polymer[J]. Phys Rev Lett,1991,66:1864-1872.
[57]Hvilsted S, Andrazzi F, Kulina C. Novel Side-Chain Liquid Crystalline Polyester Architecture for Reversible Optical Storage[J]. Macromolecules,1995,28: 2172-2179.
[58]Todorov T, Nikolova L, Tomova N. Polarization holography I:A new high-eficiency organic material with reversible photoindueed bbeffingence[J]. Appl. Opt.,1984,23: 4309-4313.
[59]傅正生,王长青,薛华丽,等.含偶氮苯光学活性侧基聚合物研究进展[J].高分子通报,2004,4,10-11
[60]车鹏超,和亚宁,王晓工.重氮偶合方法合成主链型光响应偶氮聚合物[J].高分子学报,2006,8,977-981.
[61]王瑞东,王晓工.一种主侧链均含偶氮基团的聚合物合成与研究[J].中国科技论文在线,2009,413-417.
[62]江兆建,游毅.含偶氮苯基团的阳离子表面活性剂的合成[J].合成化学,2009,246-248.
[63]宋冰蕾,赵剑曦.光敏季铵盐Gemini表面活性剂a4-6-m在气/液界面的吸附[J].物理化学学报,2009,25(10)：2020-202.
[64]Hassan N, Mohsen A. Synthesis of barbell-like triblock copolymers, dendritic triazine-block-poly(ethylene glycol)-block-dendritic triazine and investigation of their solution behaviors[J]. Polymer,2005,10788-10799.
[65]Lee C-H, Yamamoto T. Synthesis and characterization of a new class of liquid-crystalline, highly luminescent molecules containing a 2,4,6-triphenyl-1,3,5-triazine unit[J]. Tetrahedron Lett,2001,42:3993.
[66]Lupton J M, Hemingway L R, Samuel, etal. Electroluminescence from a new distyrylbenzene based triazine dendrimer[J]. J.Mater.Chem.,2000,10:867.
[67]罗春华,于美娜,赵凌,等.固态反应合成2,4,6-三苯氧基均三嗪-1,3,5-均三嗪衍生物[J].应用化学,2005,22：811.
[68]Takagi K, Hattori T, Kunisada H, et al. Triazine Dendrimers by Divergent and Convergent Methods[J]. Journal of Polymer Science:Part A:Polymer Chemistry, 2000,38:4385-4395.
[69]Anastasios P M, John A M. New crosslinkable polyimides,polyamides and polyureas derived from 2,4,6-tris(4-aminophenoxy)-s-triazine[J]. Eur.Polym.J.,1989,25: 455-460.
[70]吕荣文,张竹霞,高昆玉.芳硝基物的水合肼催化还原研究进展[J].染料与染色,2003,40：160-162.
[71]Schaefer F C, Thurston J T, Dudley J R. Cyanuric chloride derivatives.Ⅳ.Aryloxy-s-triazines[J]. J Am Chem Soc,1951,73:2900.
[72]杨进,刘习奎,汤嘉陵,等.3,5-二氨基苯甲酸-4'-联苯酯的合成[J].四川大学学报,2004,36：53-56.
[73]邢其毅,徐瑞秋,周政,等,基础有机化学[M].第二版.北京：高等教育出版社,1994.
[74]Allen G, De Boos A.G Preparation and properties of the poly(2-chlorocyanurate) of bisphenol A[J]. Polymer,1974,56-59.
[75]U. H. F. Bunz. Breath Figures as a Dynamic Templating Method for Polymers and Nanomaterials[J]. Adv. Mater.2006,18,973-989
[76]O. Pitois, B. Francois. Formation of ordered micro-porous membrance. Eur. Phys. J. B [J],1999,8,225-231
[77]何本桥,李建新,边栋材,有序多孔膜表面微球图案化[J].功能材料,2009,40,1379-1380,1384
[78]徐艳莲,林金火,胡炳环,漆酚醛胺聚合物多孔膜的制备[J].高分子学 报,2008,5,497-499
[79]Cha S W, Choi S H, Jin J I, et al. Synthesis and luminescence properties of four armed conjugated structures containing 1,3,4oxadiazole moieties[J]. J. Mater. Chem., 2003,13,1900-1904.
[80]Bredas J L, Adant C, Tackx P, et al. Third-order nonlinear optical response in organic materials:theoretical and experimental aspects[J]. Chem.Rev.,1994,94:243-278.
[81]Wang Wenjun, Wu Cheng, Gao Xuexi, et al. Studies on spectra and nonlinear optical properties of NMOB in langmuirblodgett films[J]. Chin. J. Lasers(中国激光),2005, 32:1123-1126(in Chinese).
[82]Zhao D X, Andreazza C, Andreazza P, et al. Bufer layer efect on ZnO nanorods growth alignment[J]. Chem Pbys Lett,2005,408:335—338.
[83]刘艳凤,花成文,苟小锋,等.三嗪类氮杂环蕃的合成与表征[J].有机化学,2009,1419-1422.