Abstract
In this study, we have investigated different reaction conditions for defect suppression in polythiophene derivatives synthesized by direct (hetero)arylation polymerization (DHAP). The well-known PQT12 polymer was used as a model due to its simple structure which facilitated analysis. 2-Bromo-3,4′-didodecyl-2:2′,5′:2″,5″:2‴-quaterthiophene and 2-bromo-3″,4‴-didodecyl-2:2′,5′:2″,5″-2‴-quaterthiophene monomers allowed the analysis of both homocoupling defects and β-branching defects due to their asymmetric structure as well as the effect of β-protection. The properties of the resulting polymers were analyzed using size-exclusion chromatography, differential scanning calorimetry, UV–visible absorption spectroscopy, and 1H NMR spectrometry. Some model compounds were synthesized to help with end-groups analysis, revealing debromination as the main obstacle to chain growth. The highest quality polymer was obtained when using toluene as a solvent, Pd2dba3 as a palladium(0) catalyst, neo-decanoic acid (NDA) as a carboxylic acid additive, and a dual-ligand system with diamine TMEDA and phosphine P(o-OMePh)3. This study also revealed the importance of the choice of the monomers for the preparation of well-defined conjugated polymers.
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