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Direct Arylation Polycondensation of Bithiazole Derivatives with Various Acceptors

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Tsukuba Research Center for Interdisciplinary Materials Science (TIMS), Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba 305-8573, Japan
*E-mail [email protected] (J.K.).
*E-mail [email protected] (T.K.).
Cite this: Macromolecules 2014, 47, 21, 7378–7385
Publication Date (Web):October 24, 2014
https://doi.org/10.1021/ma5014397
Copyright © 2014 American Chemical Society
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Abstract

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Novel π-conjugated polymers with a bithiazole unit and various acceptor units were synthesized by polycondensation via Pd-catalyzed direct arylation. The results of polycondensation reactions depend on chalcogen elements in the monomers. The presence of a Se atom inhibited polymerization, presumably owing to the coordination of the Se moiety to the Pd center; the issue was resolved by increasing the reaction temperature (120 °C). The chalcogen elements also affected the interchain interactions of the obtained polymers. The strong interchain interactions led to low solubility, high crystallinity, and a large red-shift of absorption in the film state compared with that in the solution state. Absorption spectra and DFT calculations revealed that the bithiazole units served as weak donor units in case that the bithiazole units were directly connected to strong acceptor units. The combination of the bithiazole units with the strong acceptor units afforded deep HOMO–LUMO levels.

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Experimental details, characterization data, mass spectra of the compounds, DSC, and TGA curves. This material is available free of charge via the Internet at http://pubs.acs.org.

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