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Indandione‐Terminated Quinoids: Facile Synthesis by Alkoxide‐Mediated Rearrangement Reaction and Semiconducting Properties
Author(s) -
Du Tian,
Gao Ruiheng,
Deng Yunfeng,
Wang Cheng,
Zhou Qian,
Geng Yanhou
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201911530
Subject(s) - delocalized electron , alkene , alkoxide , homo/lumo , chemistry , aryl , molecular orbital , photochemistry , molecule , catalysis , organic chemistry , alkyl
A series of 1,3‐indandione‐terminated π‐conjugated quinoids were synthesized by alkoxide‐mediated rearrangement reaction of the respective alkene precursors, followed by air oxidation. This new protocol allows access to quinoidal compounds with variable termini and cores. The resulting quinoids all show LUMO levels below −4.0 eV and molar extinction coefficients above 10 5 L mol −1 cm −1 . The optoelectronic properties of these compounds can be regulated by tuning the central cores as well as the aryl termini ascribed to the delocalized frontier molecular orbitals over the entire molecular skeleton involving aryl termini. n‐Channel organic thin‐film transistors with electron mobility of up to 0.38 cm 2 V −1 s −1 were fabricated, showing the potential of this new class of quinoids as organic semiconductors.