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Simple Synthesis of P(Cbz‐ alt ‐TBT) and PCDTBT by Combining Direct Arylation with Suzuki Polycondensation of Heteroaryl Chlorides
Author(s) -
Lombeck Florian,
Matsidik Rukiya,
Komber Hartmut,
Sommer Michael
Publication year - 2015
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.201400437
Subject(s) - comonomer , yield (engineering) , chemistry , nuclear magnetic resonance spectroscopy , condensation polymer , nuclear chemistry , polymer chemistry , materials science , organic chemistry , polymer , polymerization , metallurgy
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 (TBTCl 2 ) and 4,7‐bis(5‐chloro‐4‐hexyl‐2‐thienyl)‐2,1,3‐benzothiadiazole (DH‐TBTCl 2 ) in one step. Suitable conditions of the Suzuki polycondensations (SPC) of TBTCl 2 and DH‐TBTCl 2 with the carbazole comonomer CbzPBE 2 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).