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Issue 60, 2020
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How does excited-state antiaromaticity affect the acidity strengths of photoacids?

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Abstract

Photoacids like substituted naphthalenes (X = OH, NH3+, COOH) are aromatic in the S0 state and antiaromatic in the S1 state. Nucleus independent chemical shifts analyses reveal that deprotonation relieves antiaromaticity in the excited conjugate base, and that the degree of “antiaromaticity relief” explains why some photoacids are stronger than others.

Graphical abstract: How does excited-state antiaromaticity affect the acidity strengths of photoacids?

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Article information


Submitted
23 Apr 2020
Accepted
18 May 2020
First published
27 May 2020

Chem. Commun., 2020,56, 8380-8383
Article type
Communication
Author version available

How does excited-state antiaromaticity affect the acidity strengths of photoacids?

Z. Wen, L. J. Karas, C. Wu and J. I. Wu, Chem. Commun., 2020, 56, 8380 DOI: 10.1039/D0CC02952A

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