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Bithiazole-based poly(arylenevinylene) is synthesized via the Co-catalyzed hydroarylation polyaddition of N,N,N′,N′-tetrahexyl-(2,2′-bithiazole)-4,4′-dicarboxamide with 2,7-diethynyl-9,9-bis(2-ethylhexyl)fluorene in a regioselective manner. The introduction of the 2,2′-bithiazole unit deepens the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels of the polymer compared to the analogous bithiophene-based poly(arylenevinylene). N-Methylation and N-oxidation of the thiazole moiety further deepen the HOMO and LUMO energy levels of the polymer, which is attributed to the enhanced electron-withdrawing effect. The N-oxidized polymer exhibits a high photoluminescence quantum yield and serves as an emitting material in an organic light-emitting diode, and its deep HOMO energy level efficiently restrains the trapping of holes in the host poly(vinylcarbazole) matrix.

Rights:

• Creative Commons BY-NC-ND Attribution-NonCommercial-NoDerivs 4.0 International
  

Keyword: Poly(arylenevinylene)s, Organic light-emitting diode

Date published: 2025-02-07

Publisher: Wiley

Journal:

• Macromolecular Rapid Communications (ISSN: 10221336) vol. 46 issue. 9

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Manuscript type: Publisher's version (Version of record)

MDR DOI:

First published URL: https://doi.org/10.1002/marc.202401082

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Updated at: 2025-05-07 17:14:54 +0900

Published on MDR: 2025-05-08 08:18:59 +0900