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

Ayane Kayama; Akihiro Shimizu; Ryo Shintani

doi:10.1055/a-1543-4018

Synthesis, Table of Contents

Synthesis 2021; 53(21): 4042-4047
DOI: 10.1055/a-1543-4018

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

Ayane Kayama

,

Akihiro Shimizu ∗

,

Ryo Shintani ∗

Abstract

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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 solvatochromism

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References

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