Journal
MACROMOLECULAR RAPID COMMUNICATIONS
Volume 36, Issue 2, Pages 231-237Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/marc.201400437
Keywords
conjugated polymers; direct arylation; heteroaryl chlorides; homocoupling; Suzuki polycondensation
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Funding
- Fonds der Chemischen Industrie (FCI)
- Innovationsfond Forschung of the University of Freiburg
- DFG [SPP 1355, IRTG 1642]
- EPSRC
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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 (DHTBTCl 2) in one step. Suitable conditions of the Suzuki polycondensations (SPC) of TBTCl2 and DH-TBTCl2 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).
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