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Intramolecular Charge Transfer‐Enhanced BODIPY Photosensitizer in Photoinduced Electron Transfer and Its Application to Photoxidation under Mild Condition
Author(s) -
Wang Ruiqin,
Geng Ying,
Zhang Lili,
Wu Wenting,
Fan Weiyu,
Li Zhongtao,
Wang Lizhuo,
Zhan Liying,
Wu Xueyan,
Wu Mingbo
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201500494
Subject(s) - chemistry , bodipy , photoinduced electron transfer , photosensitizer , photochemistry , intramolecular force , electron transfer , conjugated system , redox , organic chemistry , fluorescence , polymer , physics , quantum mechanics
Photoinduced electron transfer process is a crucial step in photooxidation to obtain synthetic chemicals. However, the driving forces of electron transfer as priority in all have been rarely studied in stepwise detail. Herein, we report a series of BODIPY derivatives with an emphasis on the intramolecular charge transfer, enhancing the key step of photoinduced electron transfer process and photooxidation performances. A series of novel BODIPY photosensitizers ( B‐1 – B‐5 ) were prepared, wherein diethylamine amino of B‐3 as charge injection group was conjugated to the 2,6‐diiodo‐styryl‐BODIPY, and the electron transfer impetus was enhanced 1.6 times due to its more negative redox potentials. These results were also confirmed by the DFT/TDDFT calculation. Without pure oxygen, B‐3 still can exhibit an exceptional performance in photoxidative aromatization of 1,4‐DHP under mild condition. After irradiation for 28 min, the conversion rate came to 98.2%.