Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Substituent Effects at the 5-Position of 3-[bis(pyridine-2-ylmethyl)amino]-BODIPY Cation Sensor Used for Ratiometric Quantification of Cu2+
Akira HafukaRyosuke KandoKohei OhyaKoji YamadaSatoshi OkabeHisashi Satoh
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JOURNAL RESTRICTED ACCESS Advance online publication

Article ID: 20140273


In this paper, we investigated the effects of substitution at the 5-position of an asymmetric BODIPY cation sensor to tune its spectroscopic, photophysical, and cation-sensing properties. We introduced substituent groups with differing electron density at the 5-position of 3-[bis(pyridine-2-ylmethyl)amino]-BODIPY, which contains a cation recognition moiety at the 3-position of the BODIPY core, to develop four sensors which all exhibited distinctive ratiometric spectral changes in the presence of Cu2+. Aromatic substitution increased the Stokes shift. Substitution with the electron-withdrawing sulfonylphenyl group resulted in the highest fluorescence quantum yield, largest absorption coefficient, and largest spectral shift in the presence of Cu2+. The sulfonylphenyl-substituted sensor also exhibited excellent selectivity for Cu2+.

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