Orthogonally aligned cyclic BODIPY arrays with long-lived triplet excited states as efficient heavy-atom-free photosensitizers |
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Authors: | Zhaoyang Zhu Xue Zhang Xing Guo Qinghua Wu Zhongxin Li Changjiang Yu Erhong Hao Lijuan Jiao Jianzhang Zhao |
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Institution: | Laboratory of Functionalized Molecular Solids, Ministry of Education, College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241002 China.; State Key Laboratory of Fine Chemicals, School of Chemical Engineering, Dalian University of Technology, Dalian 116024 China, |
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Abstract: | 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 1O2 and O2−˙ under light irradiation.Cyclic BODIPY trimers showed strong exciton coupling in singlet excited states and long-lived triplet excited states, and generated both singlet oxygen and superoxide radicals under light irradiation, giving good reactive oxygen quantum yields and promising PDT results in vitro. |
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