高等学校化学学报

高等学校化学学报 ›› 2005, Vol. 26 ›› Issue (9): 1743.

• 研究论文 • 上一篇    下一篇

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

陈令武, 成义祥, 宋金峰, 邹小伟   

  1. 南京大学化学化工学院, 南京210093
  • 收稿日期:2004-09-29 出版日期:2005-09-10 发布日期:2005-09-10
  • 基金资助:

    国家自然科学基金(批准号:20474028);江苏省自然科学基金(批准号:BK2004086)资助.

Synthesis and Properties of Chiral Conjugated Polymer Incorporating (R)- and (S)-1,1'-Binaphthyl and Oxadiazole Units

CHEN Ling-Wu, CHENG Yi-Xiang, SONG Jin-Feng, ZOU Xiao-Wei   

  1. College of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
  • Received:2004-09-29 Online:2005-09-10 Published:2005-09-10

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被引次数

9

摘要： 在Pd(PPh3)4催化下,将单体(S)-6,6'-二溴-2,2'-二正丁氧基-1,1'-联萘[(S)-M-1]和(R)-6,6'-二溴-2,2'-二正丁氧基-1,1'-联萘[(R)-M-1]分别与2,5-二(4-三正丁基锡基苯)-1,3,4-噁二唑(M-2)通过Stille交叉耦合反应合成了手性高分子P-1与P-2,并用1HNMR、13CNMR、FTIR、UV、热分析、荧光光谱、GPC和CD等分析方法进行了表征.手性高分子P-1和P-2都能发射较强的蓝色荧光;在高分子侧链上引入丁氧基后使得手性高分子的溶解性能增强,并具有良好的成膜性能;在高分子主链引入亲电子的噁二唑生色团能使其特别适合于作为空穴电子传输层,对氧和热特别稳定,是一类潜在的光电高分子材料.

关键词: (R)/(S)-BINOL, 手性高分子, 荧光光谱, 圆二色谱, Stille反应

Abstract: Chiral conjugated polymers P-1 and P-2 were obtained by the polymerization of (S)-6,6'-dibromo-2,2'-bisbutoxy-1,1'-binaphthyl and (R)-6,6'-dibromo-2,2'-bisbutoxy-1,1'-binaphthyl with 2,5-bis(tri-n-butyltinphenyl)-1,3,4-oxadiazole(M-2) respectively via Stille coupling reaction catalyzed by Pd(PPh3)4. Both monomers and polymers were characterized by NMR, MS, FTIR, UV, DSC-TG, fluorescent spectroscopy, GPC and CD spectra. The butoxy substitutents on binaphthyl rings as a side chain of the polymers can improve the solubility in organic solvents and facile electro-optical sensors. 1,3,4-Oxadiazole unit is a better chromophore, and has good hole-transporting and stability for oxygen and heat. The polymers can emit very strong blue fluorescence. They are expected to have the potential application in the materials of interesting electro-optical molecular sensors.

Key words: (R)/(S)-BINOL, Chiral polymer, Fluorescence spectrum, CD spectrum, Stille reaction

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