含五氟苯的噻吩并吡咯二酮-苯并二噻吩共轭聚合物的合成及其性能  

Synthesis and Properties of Pentafluorobenzene-substituted Thieno[3,4-c] pyrrole-4,6-dione and Benzo[1,2-b∶5,5-b'] dithiophene Conjugated Polymers

作　　者：黄燕春[1] 周铭露[1] 王淑惠[1] 陈惠敏[1] 李萍萍[1] 王文[1] 

机构地区：[1]福建师范大学材料科学与工程学院福建省高分子材料重点实验室,福建福州350007

出　　处：《合成化学》2016年第8期673-677,共5页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21574021;51573026);福建省自然科学基金资助项目(2015J01189)

摘　　要：以3,4-噻吩二甲酸和五氟苯胺为起始原料,经酰化、缩合和NBS溴代反应制得2,5-二溴-5-五氟苯基噻吩[3,4-c]吡咯-4,6-二酮(2);2经两步反应制得2-溴-2,5-二噻吩-5-五氟苯基噻吩[3,4-c]吡咯-4,6-二酮(4);以苯并二噻吩衍生物(BDT1和BDT2)为给体单元,2或4为受体单元,分别经Stille偶联缩聚反应合成了3个含五氟苯的噻吩并吡咯二酮-苯并二噻吩共轭共聚物(5a^5c),其结构和性能经1H NMR,13C NMR,UV-Vis,TGA和循环伏安法表征。结果表明:5a,5b和5c的最大吸收峰分别位于559 nm,559 nm和547 nm,光学带隙分别为1.70 e V,1.73 e V,1.68 e V(薄膜)和1.84 e V,1.83 e V,1.81 e V(甲苯);失重5%的温度为307~325℃;5a^5c的起始氧化电位和起始还原电位分别为1.14 V,1.18 V,1.03 V和-0.67 V,-0.67 V,-0.70 V;HOMO和LUMO能级分别为-5.54 e V,-5.58 e V,-5.43 e V和-3.73 e V,-3.73 e V,-3.70 e V。2,5-Dibromo-5-perfluorophenylthieno[3,4-c]pyrrole-4,6-dione（2） was obtained by the re-action of acylation, condensation and NBS-bromination, using thiophene-3, 4-dicarboxylic acid and pentafluoroaniline as starting materials.2-Bromine-2,5-dithiophene-5-pentafluorphenyl thiophene[3,4-c]pyrrole-4,6-dione（4） was prepared by a two-step reaction from 2.Three pentafluorobenzene-substi-tuted thieno[3,4-c] pyrrole-4,6-dione and benzo[1,2-b ∶5,5-b′] dithiophene conjugated polymers （5a^5c ） were synthesized by Stille coupling condenstation, using dibenzothiophene （ BDT1 and BDT2 ） as donors and 2 or 4 as acceptors, respectively.The structures and properties were character-ized by 1 H NMR, 13 C NMR, UV-Vis, TGA and CV.The results showed that λmax of 5a, 5b and 5c were at 559 nm, 559 nm and 547 nm, respectively.T5 of 5a^5c were 307~325℃.The optical band＆amp;nbsp;gaps of 5a^5c were 1.70 eV, 1.73 eV, 1.68 eV（film） and 1.84 eV, 1.83 eV, 1.81 eV（toluene）, re-spectively.The initial oxidation potentials and initial reduction potentials were 1.14 V, 1.18 V, 1.03 V and -0.67 V, -0.67 V, -0.70 V, respectively.The HOMO and LUMO energy levels of 5a^5c were -5.54 eV, -5.58 eV, -5.43 eV and -3.73 eV, -3.73 eV, -3.70 eV, respectively.

关 键 词：3 4-噻吩二甲酸 苯并二噻吩 Stille偶联缩聚反应 共轭聚合物 合成 性能 

分 类 号：O626.12[理学—有机化学] O621.3[理学—化学]