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首页> 中文期刊> 《合成化学》 >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

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

         
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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 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.%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 eV，1．73 eV，1．68 eV（薄膜）和1．84 eV，1．83 eV，1．81 eV（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 eV，－5．58 eV，－5．43 eV和－3．73 eV，－3．73 eV，－3．70 eV。

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