Indandione‐Terminated Quinoids: Facile Synthesis by Alkoxide‐Mediated Rearrangement Reaction and Semiconducting Properties. Issue 1 (22nd November 2019)

• Record Type: Journal Article
• Authors: Du, Tian; Gao, Ruiheng; Deng, Yunfeng; Wang, Cheng; Zhou, Qian; Geng, Yanhou
• Is Part Of: Angewandte Chemie international edition. Volume 59:Issue 1(2020)
• Page Start: 221
• Page End: 225
• Publication Date: 2019-11-22
• Subjects: aromatic dialdehydes -- electron transport -- indandione -- organic thin-film transistor -- quinoidal compounds; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201911530
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Electronic building blocks : 1, 3‐Indandione‐terminated quinoids with various termini and central cores were synthesized by an alkoxide‐mediated rearrangement reaction. Their properties can be regulated by tuning the central cores and the aryl termini. These compounds display unipolar n‐type semiconductor characteristics with electron mobilities of up to 0.38 cm 2 V −1 s −1 .