High-yield and sustainable synthesis of quinoidal compounds assisted by keto–enol tautomerism
Open Access
- 9 June 2021
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Chemical Science
- Vol. 12 (27), 9366-9371
- https://doi.org/10.1039/d1sc01685g
Abstract
The classical synthesis of quinoids, which involves Takahashi coupling and subsequent oxidation, often gives only low to medium yields. Herein, we disclose the keto–enol-tautomerism-assisted spontaneous air oxidation of the coupling products to quinoids. This allows for the synthesis of various indandione-terminated quinoids in high isolated yields (85–95%). The origin of the high yield and the mechanism of the spontaneous air oxidation were ascertained by experiments and theoretical calculations. All the quinoidal compounds displayed unipolar n-type transport behavior, and single crystal field-effect transistors based on the micro-wires of a representative quinoid delivered an electron mobility of up to 0.53 cm2 V−1 s−1, showing the potential of this type of quinoid as an organic semiconductor.Funding Information
- National Natural Science Foundation of China (21774093, 52073209)
- Natural Science Foundation of Tianjin City (19JCYBJC18100)
- Ministry of Science and Technology of the People's Republic of China (2016YFB0401100)
- Tianjin University
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