3-[Bis(pyridin-2-ylmethyl)amino]-5-(4-carboxyphenyl)-BODIPY as Ratiometric Fluorescent Sensor for Cu2+
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 catio...
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| Online Access: | http://www.mdpi.com/1996-1944/11/5/814 |
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doaj-0f6e916193604490aaafce2c4145bac12020-11-24T23:49:41ZengMDPI AGMaterials1996-19442018-05-0111581410.3390/ma11050814ma110508143-[Bis(pyridin-2-ylmethyl)amino]-5-(4-carboxyphenyl)-BODIPY as Ratiometric Fluorescent Sensor for Cu2+Akira Hafuka0Hisashi Satoh1Koji Yamada2Masahiro Takahashi3Satoshi Okabe4Department of Integrated Science and Engineering for Sustainable Society, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, JapanDivision of Environmental Engineering, Faculty of Engineering, Hokkaido University, North-13, West-8, Sapporo 060-8628, JapanDivision of Environmental Materials Science, Graduate School of Environmental Science, Hokkaido University, North-10, West-5, Sapporo 060-0810, JapanDivision of Environmental Engineering, Faculty of Engineering, Hokkaido University, North-13, West-8, Sapporo 060-8628, JapanDivision of Environmental Engineering, Faculty of Engineering, Hokkaido University, North-13, West-8, Sapporo 060-8628, JapanWe 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.http://www.mdpi.com/1996-1944/11/5/814boron-dipyrromethenedi(2-picolyl)aminecationioncopperheavy metaltransition metaldyefluoroionophorefluorescence |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Akira Hafuka Hisashi Satoh Koji Yamada Masahiro Takahashi Satoshi Okabe |
| spellingShingle |
Akira Hafuka Hisashi Satoh Koji Yamada Masahiro Takahashi Satoshi Okabe 3-[Bis(pyridin-2-ylmethyl)amino]-5-(4-carboxyphenyl)-BODIPY as Ratiometric Fluorescent Sensor for Cu2+ Materials boron-dipyrromethene di(2-picolyl)amine cation ion copper heavy metal transition metal dye fluoroionophore fluorescence |
| author_facet |
Akira Hafuka Hisashi Satoh Koji Yamada Masahiro Takahashi Satoshi Okabe |
| author_sort |
Akira Hafuka |
| title |
3-[Bis(pyridin-2-ylmethyl)amino]-5-(4-carboxyphenyl)-BODIPY as Ratiometric Fluorescent Sensor for Cu2+ |
| title_short |
3-[Bis(pyridin-2-ylmethyl)amino]-5-(4-carboxyphenyl)-BODIPY as Ratiometric Fluorescent Sensor for Cu2+ |
| title_full |
3-[Bis(pyridin-2-ylmethyl)amino]-5-(4-carboxyphenyl)-BODIPY as Ratiometric Fluorescent Sensor for Cu2+ |
| title_fullStr |
3-[Bis(pyridin-2-ylmethyl)amino]-5-(4-carboxyphenyl)-BODIPY as Ratiometric Fluorescent Sensor for Cu2+ |
| title_full_unstemmed |
3-[Bis(pyridin-2-ylmethyl)amino]-5-(4-carboxyphenyl)-BODIPY as Ratiometric Fluorescent Sensor for Cu2+ |
| title_sort |
3-[bis(pyridin-2-ylmethyl)amino]-5-(4-carboxyphenyl)-bodipy as ratiometric fluorescent sensor for cu2+ |
| publisher |
MDPI AG |
| series |
Materials |
| issn |
1996-1944 |
| publishDate |
2018-05-01 |
| description |
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. |
| topic |
boron-dipyrromethene di(2-picolyl)amine cation ion copper heavy metal transition metal dye fluoroionophore fluorescence |
| url |
http://www.mdpi.com/1996-1944/11/5/814 |
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