Resonance-Enhanced Excited-State Intramolecular Proton Transfer Emission by Base-Mediated Formation of α-Cyano-γ-lactone
This letter describes the synthesis and structural, photophysical, and theoretical properties of novel fluorescent dyes derived from 2-(2'-hydroxyphenyl)benzoxazole, functionalized by tricyanofuran or α-cyano-γ-lactone groups, prone to undergo an excited-state intramolecular proton transfer (ESIPT) process. We serendipitously found that tricyanofuran can induce the formation of the corresponding lactone in basic media, leading to a highly fluorescent derivative, owing to the formation of a merocyanine in the excited state.
Authors
- Gilles Ulrich (ORCID: https://orcid.org/0000-0002-6980-6091)
- Denis Jacquemin (ORCID: https://orcid.org/0000-0002-4217-0708)
- Adèle D. Laurent (ORCID: https://orcid.org/0000-0001-9553-9014)
- Pascal Retailleau (ORCID: https://orcid.org/0000-0003-3995-519X)
- Julien Massue (ORCID: https://orcid.org/0000-0002-0629-4949)
- Timothée Stoerkler
- Théo Andris (ORCID: https://orcid.org/0009-0008-6519-2046)
Institutions
- Centre National de la Recherche Scientifique (FR)
- Institut Universitaire de France (FR)
- Université Paris-Saclay (FR)
- Institut de Chimie (FR)
- Chimie et Interdisciplinarité, Synthèse, Analyse, Modélisation (FR)
- Nantes Université (FR)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-11-24
- DOI
- https://doi.org/10.1021/acs.orglett.5c04134
- Citations
- 2
- Primary Topic
- Photochemistry and Electron Transfer Studies
- Type
- article
- Field-Weighted Citation Impact
- 3.51