Issue 38, 2022

Conjugation between 3D and 2D aromaticity: does it really exist? The case of carborane-fused heterocycles

Abstract

Although several synthesized icosahedral carborane fused 2D π-ring systems are known, and even considerable conjugation has been noted between them in some cases, the phenomenon itself is not fully understood. Based on the results of our computational study, it can be concluded that the 2D aromatic character of the fused (exo) five-membered ring is low, even in cases where significant conjugation was proposed in previous studies. Moreover, the carborane moiety constricts the bonding properties of the exo ring, thus prohibiting or promoting different Lewis resonance structures. These results will shed further light on the design and electronic modulation of new carborane-based materials.

Graphical abstract: Conjugation between 3D and 2D aromaticity: does it really exist? The case of carborane-fused heterocycles

Supplementary files

Article information

Article type
Edge Article
Submitted
23 jún. 2022
Accepted
02 sep. 2022
First published
06 sep. 2022
This article is Open Access

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

Chem. Sci., 2022,13, 11388-11393

Conjugation between 3D and 2D aromaticity: does it really exist? The case of carborane-fused heterocycles

D. Buzsáki, M. B. Kovács, E. Hümpfner, Z. Harcsa-Pintér and Z. Kelemen, Chem. Sci., 2022, 13, 11388 DOI: 10.1039/D2SC03511A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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