Highly selective synthesis of triptycene o-quinone derivatives and their optical and electrochemical properties |
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Authors: | Jian-Min Zhao Hai-Yan Lu Yi Jiang Chuan-Feng Chen |
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Affiliation: | a Beijing National Laboratory for Molecular Sciences, Center for Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China b Graduate School, Chinese Academy of Sciences, Beijing 100049, China |
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Abstract: | A convenient and efficient method for the selective synthesis of a series of triptycene o-quinone derivatives is described. The triptycene o-quinones, especially the ones containing the methoxy group(s) (electron donor) and the o-quinone group(s) (electron acceptor) simultaneously, show interesting intramolecular CT interactions and electrochemical properties. Moreover, DFT calculations display that introducing a strong electron-donor group into triptycene o-quinone results in an increasing of the HOMO energy level, which subsequently decreases the HOMO-LUMO energy gap. |
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Keywords: | Triptycene o-quinone Selective synthesis Intramolecular CT interaction Optical and electrochemical properties DFT calculation |
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