Issue 28, 2024

π-Conjugation effects on excited-state intermolecular proton-transfer reactions of anthracene–urea derivatives in the presence of acetate anions

Abstract

This study investigated emissive urea compounds with an anthryl moiety on one side and a substituent group (biphenyl, naphthyl, benzyl, or cyclohexyl) on the other side across from the urea group. This was performed to determine the contribution of π-conjugation on a substituent group to excited-state intermolecular proton-transfer (ESPT) reactions in the presence of acetate anions. Fluorescence lifetime measurements revealed that the rate constant of the ESPT reaction from the normal form to the tautomer form increased with the length of the π-conjugation. Considering that there were a few differences among the wavelengths of the fluorescence maxima for the anthracene–urea derivatives in the presence of acetate anions, we observed that the extension of π-conjugation promoted tautomer formation. This maintained the energy levels of the normal and tautomer forms in the excited state. Furthermore, an anthracene–urea derivative without π-conjugation did not undergo a reverse ESPT reaction, implying that π-conjugation is considerably involved in the reverse ESPT reaction from the tautomer form to the normal form.

Graphical abstract: π-Conjugation effects on excited-state intermolecular proton-transfer reactions of anthracene–urea derivatives in the presence of acetate anions

Supplementary files

Article information

Article type
Paper
Submitted
04 May 2024
Accepted
27 Jun 2024
First published
28 Jun 2024

Phys. Chem. Chem. Phys., 2024,26, 19176-19186

π-Conjugation effects on excited-state intermolecular proton-transfer reactions of anthracene–urea derivatives in the presence of acetate anions

A. Tachibanaki, T. Matsui and Y. Nishimura, Phys. Chem. Chem. Phys., 2024, 26, 19176 DOI: 10.1039/D4CP01869A

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