3-[Bis(pyridin-2-ylmethyl)amino]-5-(4-carboxyphenyl)-BODIPY as Ratiometric Fluorescent Sensor for Cu2

Materials
Akira HafukaSatoshi Okabe

Abstract

We developed an asymmetric fluorescent sensor 1 for Cu2+, based on 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY), by introducing 4-carboxyphenyl and bis(pyridin-2-ylmethyl)amine groups at the 5- and 3-positions, respectively, of the BODIPY core. We then investigated the photophysical and cation-sensing properties of the sensor. BODIPY 1 showed large absorption and fluorescence spectral shifts on binding to Cu2+. The fluorescence peak at 580 nm red-shifted to 620 nm. The binding stoichiometry of BODIPY 1 and Cu2+ was 1:3. The ratio of the fluorescence intensity at 620 nm to that at 580 nm (F620/F580) increased with increasing concentration of Cu2+ (3⁻10 equiv); this enabled ratiometric determination of Cu2+. Although BODIPY 1 showed good selectivity for Cu2+, there was an interfering effect of Fe3+. BODIPY 1 could be used for the naked-eye detection of Cu2+ in a water-containing sample.

References

Jun 25, 2003·Toxicology·Lisa M Gaetke, Ching Kuang Chow
Sep 30, 2005·Journal of the American Chemical Society·Julia L BricksKnut Rurack
Jan 8, 2010·Journal of the American Chemical Society·Dylan W DomailleChristopher J Chang
Jul 29, 2011·Chemical Society Reviews·Noël BoensWim Dehaen
Aug 19, 2011·Dalton Transactions : an International Journal of Inorganic Chemistry·Zeng-chen LiuMi-hui Yan
Mar 5, 2014·Chemical Reviews·Kyle P CarterAmy E Palmer
Jan 25, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Changli ZhangWeijiang He

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Citations

Apr 24, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·İpek ÖmeroğluMahmut Durmuş

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Methods Mentioned

BETA
NMR
column chromatography
Fluorescence

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