Impact of Heteroatom Substitution on Dual-State Emissive Rigidified 2-(2’-hydroxyphenyl)benzazole Dyes: Towards Ultra-Bright ESIPT Fluorophores** |
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Authors: | Dr Thibault Pariat Dr Maxime Munch Martyna Durko-Maciag Prof Dr Jaroslaw Mysliwiec Dr Pascal Retailleau Dr Pauline M Vérité Prof Dr Denis Jacquemin Dr Julien Massue Dr Gilles Ulrich |
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Institution: | 1. Institut de Chimie et Procédés pour l'Energie, l'Environnement et la Santé (ICPEES), UMR CNRS 7515, Ecole Européenne de Chimie, Polymères et Matériaux (ECPM), 25 Rue Becquerel, 67087 Strasbourg Cedex 02, France;2. Advanced Materials Engineering and Modeling Group, Wroclaw University of Science and Technology, Wybrzeze Wyspianskiego 27, 50370 Wroclaw, Poland;3. Laboratoire de Cristallochimie, ICSN-CNRS, 1 Avenue de la Terrasse, Bât. 27, 91198 Gif-sur-Yvette Cedex, France;4. CEISAM Lab-UMR 6230-CNRS and University of Nantes, 2 Rue de la Houssinière, 44322 Nantes, France |
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Abstract: | 2-(2’-Hydroxyphenyl)benzazole (HBX) fluorophores are well-known excited-state intramolecular proton transfer (ESIPT) emitters largely studied for their synthetic versatility, photostability, strong solid-state fluorescence and ability to engineer dual emission, thus paving the way to applications as white emitters, ratiometric sensors, and cryptographic dyes. However, they are heavily quenched in solution, due to efficient non-radiative pathways taking place as a consequence of the proton transfer in the excited-state. In this contribution, the nature of the heteroring constitutive of these rigidified HBX dyes was modified and we demonstrate that this simple structural modification triggers major optical changes in terms of emission color, dual emission engineering, and importantly, fluorescent quantum yield. Investigation of the photophysical properties in solution and in the solid state of a series of ethynyl-TIPS extended HBX fluorophores, along with ab initio calculations demonstrate the very promising abilities of these dyes to act as bright dual-state emitters, in both solution (even in protic environments) and solid state. |
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Keywords: | ab initio calculations benzimidazoles ESIPT fluorescence heterocycles |
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