ArticleRSC advances2020
Impact of benzannulation on ESIPT in 2-(2'-hydroxyphenyl)-oxazoles: a unified perspective in terms of excited-state aromaticity and intramolecular charge transfer.
Article in RSC advances, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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Who cites it
2 citing papers in PubMed, 27 citations in OpenAlex.
- Theoretical Insights Into the Effect of π-Conjugation Extension on Photophysical Properties and ESIPT Behavior of a Novel Benzimidazole-Based Fluorophore.Journal of fluorescence · 2026Article
- Excited-state intramolecular proton transfer with and without the assistance of vibronic-transition-induced skeletal deformation in phenol-quinoline.RSC advances · 2021Article
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Authors and funding
3 authors at 2 institutions in 2 countries.
Funding
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Abstract
Hydroxyphenyl-azoles are among the most popular ESIPT (Excited State Intramolecular Proton Transfer) scaffolds and as such, they have been thoroughly studied. Nevertheless, some aspects regarding the interplay between the emissive properties of these fluorophores and the size of their π-conjugated framework remain controversial. Previous studies have demonstrated that benzannulation of 2'-hydroxyphenyl-oxazole at the phenol group of the molecule can lead to either red- or blue-shifted fluorescence emission, depending on the site where it occurs. In this report, benzannulation at the heterocyclic unit (the oxazole site) is analysed in order to get the whole picture. The extension of π-conjugation does not significantly affect the ESIPT emission wavelength, but it leads instead to higher energy barriers for proton transfer in the first excited singlet state, as a consequence of dramatic changes in the charge transfer character of excitation caused by successive benzannulation. Theoretical calculations revealed an interesting connection between intramolecular charge transfer and excited-state aromaticity in the S
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