High-yield and sustainable synthesis of quinoidal compounds assisted by keto–enol tautomerism |
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| Authors: | Cheng Wang Tian Du Yunfeng Deng Jiarong Yao Riqing Li Xuxia Zhao Yu Jiang Haipeng Wei Yanfeng Dang Rongjin Li Yanhou Geng |
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| Affiliation: | School of Materials Science and Engineering, Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Tianjin University, Tianjin 300072 China.; Tianjin Key Laboratory of Molecular Optoelectronic Sciences, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072 China.; Joint School of National University of Singapore and Tianjin University, International Campus of Tianjin University, Binhai New City, Fuzhou 350207 China |
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| 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.Facilitated by the highly efficient Pd-catalyzed coupling and keto–enol-tautomerism-assisted spontaneous air oxidation, various indandione-terminated quinoidal compounds have been synthesized in isolated yields up to 95%. |
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