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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...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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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. |
format | Online Article Text |
id | pubmed-8597848 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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