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Synthesis and Photophysics of BF 2 ‐Rigidified Partially Closed Chain Bromotetrapyrroles: Near Infrared Emitters and Photosensitizers
Author(s) -
Dai En,
Pang Weidong,
Zhang XianFu,
Yang Xudong,
Jiang Ting,
Zhang Ping,
Yu Changjiang,
Hao Erhong,
Wei Yun,
Mu Xiaolong,
Jiao Lijuan
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201500118
Subject(s) - singlet oxygen , photochemistry , chemistry , fluorescence , molar absorptivity , alkyl , infrared , singlet state , phosphorescence , pyrrole , oxygen , excited state , organic chemistry , physics , quantum mechanics , nuclear physics , optics
We report the synthesis, crystallographic, optical, and triplet and singlet oxygen generation properties of a series of BF 2 ‐rigidified partially closed chain bromotetrapyrroles as near infrared emitters and photosensitizers. These novel dyes were efficiently synthesized from a nucleophilic substitution reaction between pyrroles and the 3,5‐bromo‐substituents on the tetra‐ and hexabromoBODIPYs and absorb in the near‐infrared region (681–754 nm) with high molar extinction coefficients. Their fluorescent emission (708–818 nm) and singlet oxygen generation properties are significantly affected by alkyl substitutions on the two uncoordinated pyrrole units of these dyes and the polarity of solvents. Among them, dyes 4 ca and 4 da show good singlet oxygen generation efficiency and good NIR fluorescence emission (fluorescence quantum yields of 0.14–0.43 in different solvents studied).