期刊
ACS MACRO LETTERS
卷 3, 期 8, 页码 819-823出版社
AMER CHEMICAL SOC
DOI: 10.1021/mz5004147
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资金
- Fonds der Chemischen Industrie (FCI)
- Research Innovation Fund of the University of Freiburg
- DFG [SPP1355]
- IRTG Soft Matter Science Graduate Program [1642]
- EPSRC
Homocouplings are identified as major side reactions in direct arylation polycondensation (DAP) of 4,7-bis(4-hexyl-2-thienyl)-2,1,3-benzothiacliazole (TBT) and 2,7-dibromo-9-(1-octylnonyl)-9H-carbazole (CbzBr(2)). Using size exclusion chromatography (SEC) and NMR spectroscopy, we demonstrate that both TBT and Cbz homocouplings occur at a considerable extent. TBT homocoupling preferentially occurs under phosphine-free conditions but can be suppressed in the presence of a phosphine ligand. Cbz homocoupling is temperature-dependent and more prevalent at higher temperatures. By contrast, evidence for chain branching as a result of unselective C-H arylation is not found for this monomer combination. These results emphasize that particular attention has to be paid to homocouplings in direct arylation polycondensations as a major source of main-chain defects, especially under phosphine-free conditions.
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