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Issue 34, 2019
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Synthesis and electrochromic behavior of a multi-electron redox-active N-heteroheptacenequinone

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Abstract

We report a novel N-heteroheptacenequinone derivative (C6OAHCQ) as a large π-conjugated framework. C6OAHCQ shows good electron-accepting behaviour owing to eight electron-deficient imino-N atoms and two carbonyl moieties and excellent solubility in common organic solvents. When a potential between 0 and −2.20 V is applied, C6OAHCQ is able to accept four electrons, which is more than fullerene C60 (three electrons) could accept in this voltage range. Moreover, a solution of C6OAHCQ and nBu4NPF6 in CH2Cl2 exhibits a clearly reversible brown-to-green colour change, suggesting that C6OAHCQ has potential as an electrochromic material.

Graphical abstract: Synthesis and electrochromic behavior of a multi-electron redox-active N-heteroheptacenequinone

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Supplementary files

Article information


Submitted
10 Jun 2019
Accepted
02 Jul 2019
First published
03 Jul 2019

Org. Biomol. Chem., 2019,17, 7884-7890
Article type
Paper

Synthesis and electrochromic behavior of a multi-electron redox-active N-heteroheptacenequinone

K. Isoda, M. Matsuzaka, T. Sugaya, T. Yasuda and M. Tadokoro, Org. Biomol. Chem., 2019, 17, 7884
DOI: 10.1039/C9OB01323G

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