3‐Hydroxypyridinyl‐Substituted‐1,2,4‐Triazoles as New ESIPT Based Fluorescent Dyes: Synthesis and Structure–Fluorescence Properties Correlations

Author:

Nina‐Diogo Anthony1,Bertrand Benoît1ORCID,Thorimbert Serge1ORCID,Gontard Geoffrey1,Nassem‐Kahn Sehr2,Echeverri Andrea2,Contreras‐García Julia2ORCID,Allain Clémence3ORCID,Lemercier Gilles4ORCID,Luppi Eleonora2ORCID,Botuha Candice1ORCID

Affiliation:

1. Institut Parisien de Chimie Moléculaire CNRS Sorbonne Université Paris 75252 France

2. Laboratoire de chimie théorique Paris CNRS Sorbonne Université Paris 75252 France

3. PPSM CNRS ENS Paris‐Saclay Université Paris‐Saclay Gif‐sur‐Yvette 91190 France

4. Institut de Chimie Moléculaire de Reims (ICMR) CNRS Université de Reims Champagne‐Ardenne Moulin de la Housse, BP 1039 51687 Reims Cedex 2 France

Abstract

AbstractThis report presents the design, synthesis, and photophysical study of two new series of promising fluorescent trisubstituted triazoles, 3‐hydroxypyridinyl substituted‐1,2,4‐triazoles (PyOHTr) and 2‐pyridonyl substituted‐1,2,4‐triazoles (PyCOTr). An excited state intramolecular proton transfer (ESIPT) fluorescence mechanism is evidenced for PyOHTr molecules by ab initio theoretical calculations. These fluorescent dyes possess unique optical properties such as large Stokes shifts, dual emission, solvatochromism, solid‐state emission and, for one of them, a white light emission, rendering them particularly attractive for future applications in both medicinal chemistry and materials science.

Publisher

Wiley

Subject

Atomic and Molecular Physics, and Optics,Electronic, Optical and Magnetic Materials

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