Lombeck Florian, Matsidik Rukiya, Komber Hartmut, Sommer Michael
Makromolekulare Chemie, Universität Freiburg, Stefan-Meier-Straße 31, 79104, Freiburg, Germany; Optoelectronics Group, Cavendish Laboratory, J J Thomson Avenue, Cambridge, CB3 0HE, UK.
Macromol Rapid Commun. 2015 Jan;36(2):231-7. doi: 10.1002/marc.201400437. Epub 2014 Oct 21.
Direct arylation (DA) of 2-chlorothiophene and 2-chloro-3-hexylthiophene with 4,7-dibromo-2,1,3-benzothiadiazole is used to synthesize 4,7-bis(5-chloro-2-thienyl)-2,1,3-benzothiadiazole (TBTCl2) and 4,7-bis(5-chloro-4-hexyl-2-thienyl)-2,1,3-benzothiadiazole (DH-TBTCl2) in one step. Suitable conditions of the Suzuki polycondensations (SPC) of TBTCl2 and DH-TBTCl2 with the carbazole comonomer CbzPBE2 are established, furnishing PCDTBT and P(Cbz-alt-TBT) with high molecular weight and yield. Compared with control samples made from the corresponding dibromides, high-temperature NMR and UV-vis spectroscopy indicate similar properties for PCDTBT but an increased content of Cbz-Cbz homocouplings for P(Cbz-alt-TBT).
使用2-氯噻吩和2-氯-3-己基噻吩与4,7-二溴-2,1,3-苯并噻二唑进行直接芳基化(DA)反应,一步合成4,7-双(5-氯-2-噻吩基)-2,1,3-苯并噻二唑(TBTCl2)和4,7-双(5-氯-4-己基-2-噻吩基)-2,1,3-苯并噻二唑(DH-TBTCl2)。确定了TBTCl2和DH-TBTCl2与咔唑共聚单体CbzPBE2进行铃木缩聚反应(SPC)的合适条件,得到了高分子量和高产率的聚(咔唑-对苯撑苯并噻二唑)(PCDTBT)和聚(Cbz-alt-TBT)。与由相应二溴化物制成的对照样品相比,高温核磁共振和紫外可见光谱表明PCDTBT具有相似的性质,但聚(Cbz-alt-TBT)中Cbz-Cbz均偶联的含量增加。