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Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers

In photosensitizers, long triplet excited state lifetimes are key to their efficient electron transfer or energy transfer processes. Herein, we report a novel class of cyclic trimeric BODIPY arrays which were efficiently generated from easily accessible meso-mesityldipyrrinone and arylboronic acids...

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Autores principales: Zhu, Zhaoyang, Zhang, Xue, Guo, Xing, Wu, Qinghua, Li, Zhongxin, Yu, Changjiang, Hao, Erhong, Jiao, Lijuan, Zhao, Jianzhang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8597848/
https://www.ncbi.nlm.nih.gov/pubmed/34820111
http://dx.doi.org/10.1039/d1sc04893g
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author Zhu, Zhaoyang
Zhang, Xue
Guo, Xing
Wu, Qinghua
Li, Zhongxin
Yu, Changjiang
Hao, Erhong
Jiao, Lijuan
Zhao, Jianzhang
author_facet Zhu, Zhaoyang
Zhang, Xue
Guo, Xing
Wu, Qinghua
Li, Zhongxin
Yu, Changjiang
Hao, Erhong
Jiao, Lijuan
Zhao, Jianzhang
author_sort Zhu, Zhaoyang
collection PubMed
description In photosensitizers, long triplet excited state lifetimes are key to their efficient electron transfer or energy transfer processes. Herein, we report a novel class of cyclic trimeric BODIPY arrays which were efficiently generated from easily accessible meso-mesityldipyrrinone and arylboronic acids in one pot. Arylboronic acid, for the first time, was used to provide a boron source for BODIPY derivatives. Due to the well-defined and orthogonally aligned BODIPY cores as verified by X-ray crystallography, these BODIPY arrays show strong exciton coupling effects and efficient intersystem crossings, and are novel heavy-atom-free photosensitizers with a long-lived triplet excited state (lifetime up to 257.5 μs) and good reactive oxygen species generation efficiency (up to 0.72) contributed by both (1)O(2) and O(2)(−)˙ under light irradiation.
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spelling pubmed-85978482021-11-23 Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers Zhu, Zhaoyang Zhang, Xue Guo, Xing Wu, Qinghua Li, Zhongxin Yu, Changjiang Hao, Erhong Jiao, Lijuan Zhao, Jianzhang Chem Sci Chemistry In photosensitizers, long triplet excited state lifetimes are key to their efficient electron transfer or energy transfer processes. Herein, we report a novel class of cyclic trimeric BODIPY arrays which were efficiently generated from easily accessible meso-mesityldipyrrinone and arylboronic acids in one pot. Arylboronic acid, for the first time, was used to provide a boron source for BODIPY derivatives. Due to the well-defined and orthogonally aligned BODIPY cores as verified by X-ray crystallography, these BODIPY arrays show strong exciton coupling effects and efficient intersystem crossings, and are novel heavy-atom-free photosensitizers with a long-lived triplet excited state (lifetime up to 257.5 μs) and good reactive oxygen species generation efficiency (up to 0.72) contributed by both (1)O(2) and O(2)(−)˙ under light irradiation. The Royal Society of Chemistry 2021-10-29 /pmc/articles/PMC8597848/ /pubmed/34820111 http://dx.doi.org/10.1039/d1sc04893g Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Zhu, Zhaoyang
Zhang, Xue
Guo, Xing
Wu, Qinghua
Li, Zhongxin
Yu, Changjiang
Hao, Erhong
Jiao, Lijuan
Zhao, Jianzhang
Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers
title Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers
title_full Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers
title_fullStr Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers
title_full_unstemmed Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers
title_short Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers
title_sort orthogonally aligned cyclic bodipy arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8597848/
https://www.ncbi.nlm.nih.gov/pubmed/34820111
http://dx.doi.org/10.1039/d1sc04893g
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