Issue 25, 2023

Substituent effects on paratropicity and diatropicity in π-extended hexapyrrolohexaazacoronene

Abstract

Research into the application of antiaromatic compounds as molecular materials is an attractive strategy in the development of electronic materials. Antiaromatic compounds have traditionally been considered to be unstable, and thus, the creation of stable antiaromatic compounds has been sought in the field of organic chemistry. Recently, some studies have been reported on the synthesis, isolation, and elucidation of the physical properties of compounds with stability and definitive antiaromatic properties. In general, antiaromatic compounds are considered to be more susceptible to substituents due to their inherently narrow HOMO–LUMO gap compared to aromatic compounds. However, there have been no studies examining substituent effects in antiaromatic compounds. In this study, we have developed a synthetic method to introduce various substituents into π-extended hexapyrrolohexaazacoronene (homoHPHAC+), one of the stable and clearly antiaromatic compounds, and investigated the substituent effects on the optical, redox, and geometrical properties and paratropicity of a series of compounds. In addition, the properties of the two-electron oxidized form, homoHPHAC3+, were investigated. Control of electronic properties by introducing substituents into antiaromatic compounds provides a new design guideline for molecular materials.

Graphical abstract: Substituent effects on paratropicity and diatropicity in π-extended hexapyrrolohexaazacoronene

Supplementary files

Article information

Article type
Edge Article
Submitted
23 dez 2022
Accepted
04 jun 2023
First published
06 jun 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 7036-7043

Substituent effects on paratropicity and diatropicity in π-extended hexapyrrolohexaazacoronene

M. Takase, T. Takata, K. Oki, S. Mori and H. Uno, Chem. Sci., 2023, 14, 7036 DOI: 10.1039/D2SC07037E

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