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Synthesis 2021; 53(21): 4042-4047
DOI: 10.1055/a-1543-4018
DOI: 10.1055/a-1543-4018
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Anthracene-Based Zwitterion with a Small HOMO–LUMO Energy Gap
This work was financially supported in part by the JSPS KAKENHI Grant Number JP20H02723.
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Abstract
We have designed and synthesized an anthracene-based zwitterion, 2-methyl-2-azoniaanthracene-7-olate. The zwitterion shows amphoteric redox properties and low-energy-light absorption originating from the small HOMO–LUMO energy gap of ca. 1.7 eV. DFT calculations show that the combination of replacing the C–H with N+–Me and introducing O− is necessary to alter the electronic structure and properties of anthracene significantly.
Key words
zwitterion - small HOMO–LUMO energy gap - redox - long-wavelength light absorption - negative solvatochromismSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1543-4018.
- Supporting Information
Publication History
Received: 22 May 2021
Accepted: 02 July 2021
Accepted Manuscript online:
02 July 2021
Article published online:
12 August 2021
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