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Authors Nübling, F. ; Komber, H. ; Sommer, M.
Title All-conjugated, all-crystalline donor-acceptor block copolymers P3HT-b-PNDIT2 via direct arylation polycondensation
Date 28.02.2017
Number 52782
Abstract The synthesis and characterization of all-conjugated, all-crystalline donor–acceptor block copolymers (BCPs) containing poly(3-hexylthiophene) (P3HT) and poly{[N,N`-bis(2-octyldodecyl)naphthalene-1,4,5,8-bis(dicarboximide)-2,6-diyl]-alt-5,5´- (2,2´-bithiophene)} (PNDIT2) is presented. Direct arylation polycondensation (DAP) of dibromonaphthalenediimide and bithiophene is carried out in the presence of P3HT end-cappers to allow the in situ formation of BCPs P3HT-b-PNDIT2. As-prepared, well-defined H-P3HT-Br with hydrogen and bromine chain termini shows nonoptimal reactivity under the DAP conditions used. Therefore, H-P3HT-Br is converted into either H-P3HT-Th (thiophene) or H-P3HT-Mes (mesitylene), giving a,·-hetero-C–H functionalized P3HT with modulated C–H reactivity. The influence of the different C–H chain termini of P3HT on the ability to act as end-capper and the resulting block structures is investigated in detail using wavelength-dependent size exclusion chromatography (SEC) and NMR spectroscopy. Different C–H reactivities of a,·-hetero-C–H functionalized P3HT cause different contents of multiblocks, which in turn lead to varied degrees of crystallinity. These results show that careful tuning of C–H reactivity is a promising way to obtain well-defined, all-conjugated block copolymers via DAP.
Publisher Macromolecules
Wikidata
Citation Macromolecules 50 (2017) 1909-1918
DOI https://doi.org/10.1021/acs.macromol.7b00251
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