Starburst substituted hexaazatriphenylene compounds: synthesis, photophysical and electrochemical properties |
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Authors: | Baoxiang Gao Yueling Liu Yanxiang Cheng Xiabin Jing |
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Institution: | a Key Laboratory of Medicinal Chemistry and Molecular Diagnosis, Ministry of Education, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, PR China b State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, PR China |
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Abstract: | Starburst-substituted hexaazatriphenylene compounds have been designed and synthesized by introducing various peripheral aryl substituents to the central heterocyclic core. The effects of various substituent groups on the photophysical and electrochemical properties of the substituted hexaazatriphenylene have been investigated. Significant red-shifts of the absorption peak (from 413 nm to 530 nm) and emission peak (from 432 nm to 700 nm) were observed when the electron-donating ability of the aryl substituents was increased, corresponding to a decrease in the band gap from 2.90 eV to 2.05 eV. Introducing bulky substituents with weak electron-donating ability enhances the fluorescence quantum yield from 23% to 87%. In contrast, incorporating aryl substituents with strong electron-donating ability decreases the fluorescence quantum yield. Also, due to the extended conjugation between the aryl substituents and the hexaazatriphenylene core, the reduction potentials of the compounds were reduced and the LUMO levels were thus increased. |
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Keywords: | Hexaazatriphenylene Bandgap Fluorescence Electrochemical |
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