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Investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both Br-BTN and CN-BTN systems

In the present work, two novel Br-BTN and CN-BTN compounds have been investigated theoretically. We in-depth explore the excited state hydrogen bonding interactions and the excited state intramolecular proton transfer (ESIPT) behaviors for the Br-BTN and CN-BTN system. We firstly verify the formatio...

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Autores principales: Yang, Dapeng, Zhang, Qiaoli, Song, Xiaoyan, Zhang, Tianjie
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9067100/
https://www.ncbi.nlm.nih.gov/pubmed/35514474
http://dx.doi.org/10.1039/c9ra04258j
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author Yang, Dapeng
Zhang, Qiaoli
Song, Xiaoyan
Zhang, Tianjie
author_facet Yang, Dapeng
Zhang, Qiaoli
Song, Xiaoyan
Zhang, Tianjie
author_sort Yang, Dapeng
collection PubMed
description In the present work, two novel Br-BTN and CN-BTN compounds have been investigated theoretically. We in-depth explore the excited state hydrogen bonding interactions and the excited state intramolecular proton transfer (ESIPT) behaviors for the Br-BTN and CN-BTN system. We firstly verify the formation of hydrogen bond effects of O–H⋯N based on reduced density gradient (RDG) versus sign(λ(2))ρ. The simulated primary bond lengths and bond angles as well as infrared (IR) vibrational spectra reveal that the hydrogen bond O–H⋯N should be strengthened in the excited state. Combining the frontier molecular orbital (MO) investigations, we infer that the charge transfer phenomenon (from HOMO to LUMO) around hydrogen bonding moieties reveals the tendency of ESIPT reaction. Particularly, the increased electronic densities around proton acceptor atoms facilitate attracting a hydrogen proton, which plays a decisive role in opening the ESIPT reaction. Via constructing potential energy curves in both S(0) and S(1) states, the ultrafast ESIPT process can be verified which explains previous experimental characteristics. Furthermore, via searching the transition state (TS) structure and constructing the intrinsic reaction coordinate (IRC) reaction path, we check and confirm the ESIPT mechanism for both Br-BTN and CN-BTN systems. We sincerely hope that our theoretical work could guide novel applications based on Br-BTN and CN-BTN compounds in future.
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spelling pubmed-90671002022-05-04 Investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both Br-BTN and CN-BTN systems Yang, Dapeng Zhang, Qiaoli Song, Xiaoyan Zhang, Tianjie RSC Adv Chemistry In the present work, two novel Br-BTN and CN-BTN compounds have been investigated theoretically. We in-depth explore the excited state hydrogen bonding interactions and the excited state intramolecular proton transfer (ESIPT) behaviors for the Br-BTN and CN-BTN system. We firstly verify the formation of hydrogen bond effects of O–H⋯N based on reduced density gradient (RDG) versus sign(λ(2))ρ. The simulated primary bond lengths and bond angles as well as infrared (IR) vibrational spectra reveal that the hydrogen bond O–H⋯N should be strengthened in the excited state. Combining the frontier molecular orbital (MO) investigations, we infer that the charge transfer phenomenon (from HOMO to LUMO) around hydrogen bonding moieties reveals the tendency of ESIPT reaction. Particularly, the increased electronic densities around proton acceptor atoms facilitate attracting a hydrogen proton, which plays a decisive role in opening the ESIPT reaction. Via constructing potential energy curves in both S(0) and S(1) states, the ultrafast ESIPT process can be verified which explains previous experimental characteristics. Furthermore, via searching the transition state (TS) structure and constructing the intrinsic reaction coordinate (IRC) reaction path, we check and confirm the ESIPT mechanism for both Br-BTN and CN-BTN systems. We sincerely hope that our theoretical work could guide novel applications based on Br-BTN and CN-BTN compounds in future. The Royal Society of Chemistry 2019-07-25 /pmc/articles/PMC9067100/ /pubmed/35514474 http://dx.doi.org/10.1039/c9ra04258j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Yang, Dapeng
Zhang, Qiaoli
Song, Xiaoyan
Zhang, Tianjie
Investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both Br-BTN and CN-BTN systems
title Investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both Br-BTN and CN-BTN systems
title_full Investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both Br-BTN and CN-BTN systems
title_fullStr Investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both Br-BTN and CN-BTN systems
title_full_unstemmed Investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both Br-BTN and CN-BTN systems
title_short Investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both Br-BTN and CN-BTN systems
title_sort investigation of the intramolecular hydrogen bonding interactions and excited state proton transfer mechanism for both br-btn and cn-btn systems
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9067100/
https://www.ncbi.nlm.nih.gov/pubmed/35514474
http://dx.doi.org/10.1039/c9ra04258j
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