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Materials 2018, 11(5), 814; https://doi.org/10.3390/ma11050814

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

1
Department of Integrated Science and Engineering for Sustainable Society, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan
2
Division of Environmental Engineering, Faculty of Engineering, Hokkaido University, North-13, West-8, Sapporo 060-8628, Japan
3
Division of Environmental Materials Science, Graduate School of Environmental Science, Hokkaido University, North-10, West-5, Sapporo 060-0810, Japan
*
Author to whom correspondence should be addressed.
Received: 8 April 2018 / Revised: 7 May 2018 / Accepted: 14 May 2018 / Published: 16 May 2018
(This article belongs to the Special Issue Fluorescent Sensors for Selective Detection)
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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. View Full-Text
Keywords: boron-dipyrromethene; di(2-picolyl)amine; cation; ion; copper; heavy metal; transition metal; dye; fluoroionophore; fluorescence boron-dipyrromethene; di(2-picolyl)amine; cation; ion; copper; heavy metal; transition metal; dye; fluoroionophore; fluorescence
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Hafuka, A.; Satoh, H.; Yamada, K.; Takahashi, M.; Okabe, S. 3-[Bis(pyridin-2-ylmethyl)amino]-5-(4-carboxyphenyl)-BODIPY as Ratiometric Fluorescent Sensor for Cu2+. Materials 2018, 11, 814.

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