Anthracene-Based Zwitterion with a Small HOMO–LUMO Energy Gap

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 solvatochromism

Publikationsverlauf

Eingereicht: 22. Mai 2021

Angenommen: 02. Juli 2021

Accepted Manuscript online:
02. Juli 2021

Artikel online veröffentlicht:
12. August 2021

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