Blue-Emitting 2-(2′-Hydroxyphenyl)benzazole Fluorophores by Modulation of Excited-State Intramolecular Proton Transfer: Spectroscopic Studies and Theoretical Calculations
| Autor: | Maxime Munch, Erika Colombain, Timothée Stoerkler, Pauline M. Vérité, Denis Jacquemin, Gilles Ulrich, Julien Massue |
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| Přispěvatelé: | Massue, Julien, Institut de chimie et procédés pour l'énergie, l'environnement et la santé (ICPEES), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Matériaux et Nanosciences Grand-Est (MNGE), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS), Ecole européenne de chimie, polymères et matériaux [Strasbourg], Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Nantes université - UFR des Sciences et des Techniques (Nantes univ - UFR ST), Nantes Université - pôle Sciences et technologie, Nantes Université (Nantes Univ)-Nantes Université (Nantes Univ)-Nantes Université - pôle Sciences et technologie, Nantes Université (Nantes Univ)-Nantes Université (Nantes Univ) |
| Rok vydání: | 2022 |
| Předmět: |
Models
Molecular [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry [CHIM.THEO] Chemical Sciences/Theoretical and/or physical chemistry Spectrometry Fluorescence [CHIM.ORGA]Chemical Sciences/Organic chemistry Materials Chemistry Hydrogen Bonding Protons Physical and Theoretical Chemistry [CHIM.ORGA] Chemical Sciences/Organic chemistry Fluorescent Dyes Surfaces Coatings and Films |
| Zdroj: | Journal of Physical Chemistry B Journal of Physical Chemistry B, 2022, 126 (10), pp.2108-2118. ⟨10.1021/acs.jpcb.2c00383⟩ |
| ISSN: | 1520-5207 1520-6106 |
| DOI: | 10.1021/acs.jpcb.2c00383 |
| Popis: | International audience; This article describes the synthesis, spectroscopic studies, and theoretical calculations of nine original fluorophores based on the 2-(2′-hydroxyphenyl)benzazole (HBX) scaffold, functionalized at the 4-position of the phenol ring by ethynyl-extended aniline moieties. HBX dyes are well-known to display an excited-state intramolecular proton transfer (ESIPT) process, owing to a strong six-membered hydrogen bond in their structure that allows for an enol/keto tautomerism after photoexcitation. Appropriate electronic substitution can perturb the ESIPT process, leading to dual fluorescence, both excited tautomers emitting at specific wavelengths. In the examples described herein, it is demonstrated that the proton transfer can be finely frustrated by a modification of the constitutive heteroring, leading to a single emission band from the excited enol or keto tautomer or a dual emission with relative intensities highly dependent on the environment. Moreover, the nature of the functionalization of the N-alkylated aniline moiety also has a significant importance on the relative excited-state stabilities of the two tautomers in solution. To shed more light on these features, quantum chemical calculations by the density functional theory are used to determine the excited-state energies and rationalize the experimental spectroscopic data. |
| Databáze: | OpenAIRE |
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