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Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone

Inspired by the distinguished regulated photochemical and photophysical properties of 2-(2′-hydroxyphenyl)benzazole derivatives, in this work, the novel bis(2′-benzothiazolyl)hydroquinone (BBTHQ) fluorophore is explored, looking at its photo-induced behaviors associated with different substituted at...

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Autores principales: Zhao, Jinfeng, Liu, Chang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10458628/
https://www.ncbi.nlm.nih.gov/pubmed/37630203
http://dx.doi.org/10.3390/molecules28165951
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author Zhao, Jinfeng
Liu, Chang
author_facet Zhao, Jinfeng
Liu, Chang
author_sort Zhao, Jinfeng
collection PubMed
description Inspired by the distinguished regulated photochemical and photophysical properties of 2-(2′-hydroxyphenyl)benzazole derivatives, in this work, the novel bis(2′-benzothiazolyl)hydroquinone (BBTHQ) fluorophore is explored, looking at its photo-induced behaviors associated with different substituted atomic electronegativities, i.e., BBTHQ-SO, BBTHQ-SS and BBTHQ-Se compounds. From the structural changes, infrared (IR) vibrational variations and simulated core-valence bifurcation (CVB) indexes for the dual hydrogen bonds for the three BBTHQ derivatives, we see that low atomic electronegativity could be conducive to enhancing hydrogen bonding effects in the S(1) state. Particularly, the O(4)-H(5)⋯N(6) of BBTHQ-SO and the O(1)-H(2)⋯N(3) of BBTHQ-SSe could be strengthened to be more intensive in the S(1) state, respectively. Looking into the charge recombination induced by photoexcitation, we confirm a favorable ESDPT trend deriving from the charge reorganization of the dual hydrogen bonding regions. By constructing the potential energy surfaces (PESs) along with the ESDPT paths for the BBTHQ-SO, BBTHQ-SS and BBTHQ-Se compounds, we not only unveil stepwise ESDPT behaviors, but also present an atomic electronegativity-regulated ESDPT mechanism.
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spelling pubmed-104586282023-08-27 Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone Zhao, Jinfeng Liu, Chang Molecules Article Inspired by the distinguished regulated photochemical and photophysical properties of 2-(2′-hydroxyphenyl)benzazole derivatives, in this work, the novel bis(2′-benzothiazolyl)hydroquinone (BBTHQ) fluorophore is explored, looking at its photo-induced behaviors associated with different substituted atomic electronegativities, i.e., BBTHQ-SO, BBTHQ-SS and BBTHQ-Se compounds. From the structural changes, infrared (IR) vibrational variations and simulated core-valence bifurcation (CVB) indexes for the dual hydrogen bonds for the three BBTHQ derivatives, we see that low atomic electronegativity could be conducive to enhancing hydrogen bonding effects in the S(1) state. Particularly, the O(4)-H(5)⋯N(6) of BBTHQ-SO and the O(1)-H(2)⋯N(3) of BBTHQ-SSe could be strengthened to be more intensive in the S(1) state, respectively. Looking into the charge recombination induced by photoexcitation, we confirm a favorable ESDPT trend deriving from the charge reorganization of the dual hydrogen bonding regions. By constructing the potential energy surfaces (PESs) along with the ESDPT paths for the BBTHQ-SO, BBTHQ-SS and BBTHQ-Se compounds, we not only unveil stepwise ESDPT behaviors, but also present an atomic electronegativity-regulated ESDPT mechanism. MDPI 2023-08-08 /pmc/articles/PMC10458628/ /pubmed/37630203 http://dx.doi.org/10.3390/molecules28165951 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zhao, Jinfeng
Liu, Chang
Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone
title Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone
title_full Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone
title_fullStr Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone
title_full_unstemmed Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone
title_short Computational Insights into Excited State Intramolecular Double Proton Transfer Behavior Associated with Atomic Electronegativity for Bis(2′-benzothiazolyl)hydroquinone
title_sort computational insights into excited state intramolecular double proton transfer behavior associated with atomic electronegativity for bis(2′-benzothiazolyl)hydroquinone
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10458628/
https://www.ncbi.nlm.nih.gov/pubmed/37630203
http://dx.doi.org/10.3390/molecules28165951
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AT liuchang computationalinsightsintoexcitedstateintramoleculardoubleprotontransferbehaviorassociatedwithatomicelectronegativityforbis2benzothiazolylhydroquinone