3 years ago

An Azacrown[N,S,O]–Styryl Modified Boron–Phenylpyrrin: Coordination-Mode-Transition-Induced Colorimetric and OFF–ON–OFF Fluorescence Chemosensor for Quantifying Cu2+

An Azacrown[N,S,O]–Styryl Modified Boron–Phenylpyrrin: Coordination-Mode-Transition-Induced Colorimetric and OFF–ON–OFF Fluorescence Chemosensor for Quantifying Cu2+
Dongdong Qi, Houhe Pan, Yuting Chen, Jianzhuang Jiang, Kang Wang
A new p-azacrown[N,S,O]–styryl modified boron–phenylpyrrin compound, synchronously possessing a diethylamino receptor (C-BPP-A), has been designed and synthesized. Systematic optical studies show that C-BPP-A displays a distinct two-step fluorescence response to an increasing quantity of Cu2+, commensurate with the sequential transition from free ligand (L) to 1:1 (ML) and 2:1 (M2L) complexes: added Cu2+ ions (0–1 equiv.) are first coordinated with the p-azacrown[N,S,O] moiety of C-BPP-A, forming the 1:1 Cu2+–C-BPP-A complex and leading to significant enhancement of the fluorescence at 621 nm. Subsequently, the N atom of the diethylamino group from the Cu2+–C-BPP-A complex coordinates with the additional Cu2+ (1–2 equiv.), forming an M2L type of complex, which induces the fluorescence quenching of the 1:1 Cu2+–C-BPP-A complex at 621 nm. Meanwhile, successively increasing the added Cu2+, from 0 to 1 equiv. and from 1 to 2 equiv., also induces a gradual/fast increase, respectively, in the two-absorption-band ratio I530/I603, accompanied by an obvious change in the solution color from blue to violet to purple. These results show C-BPP-A to be the first highly sensitive colorimetric, OFF–ON–OFF fluorescence, and absorption-ratiometric sensor for quantitative Cu2+ detection.A new p-azacrown[N,S,O]–styryl modified boron–phenylpyrrin compound, possessing a diethylamino receptor, acts as a highly sensitive colorimetric and OFF–ON–OFF fluorescence sensor for quantifying Cu2+ associated with the sequential transition from free ligand (L) to 1:1 (ML) and 2:1 (M2L) complexes, due to the different Cu2+ complexing affinities of the p-azacrown[N,S,O] and diethylamino moieties.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/ejic.201700653

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