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A new pH fluorescent molecular switch by modulation of twisted intramolecular charge transfer with protonation
Author(s) -
Shen Ping,
Xiao Shuzhang,
Zhan Xuqin,
Zhang Wei,
Chang Kedi,
Yang Changying
Publication year - 2013
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3185
Subject(s) - protonation , chemistry , deprotonation , fluorescence , intramolecular force , imidazole , photochemistry , molecular switch , aqueous solution , molecule , stereochemistry , organic chemistry , ion , physics , quantum mechanics
A pH fluorescent molecular switch, BOPIM‐dma, a boron 2‐(2′‐pyridyl) imidazole complex derivatives, was investigated in aqueous system. BOPIM‐dma shows weak or no fluorescence in conventional solvents due to twisted intramolecular charge transfer (TICT). Upon protonation of the dimethylamino groups in BOPIM‐dma, its fluorescence was turned on ascribed to the inhibition of TICT. Its emission can be switched ‘on’ or ‘off’ between pH 2.4 and 4.0, and it undergoes a reversible protonation–deprotonation reaction with a p K a of 3.12. Copyright © 2013 John Wiley & Sons, Ltd.