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Rhodamine based fluorescent chemosensor for Al3+: Is it possible to control metal ion selectivity of rhodamine-6G based chemosensor?

Abstract

A rhodamine derivative, 3',6'-bis(ethylamino)-2-(2-(2-hydroxy-5-methylbenzylideneamino)ethyl)-2',7'-dimethylspiro[isoindoline-1,9'-xanthen]-3-one (HL-Me), has been found to be highly selective and sensitive fluorescent chemosensor for Al3+. It has been synthesized by condensation between N-(rhodamine-6G)lactam-ethylenediamine (L1) and 5-methylsalicaldehyde (1:1) in acetonitrile and characterized by standard methods including single crystal X-ray diffraction analysis. Absorption and emission spectra have been obtained in 10 mM HEPES buffer at pH 7.4 in H2O/MeOH =1:9 (v/v) at 25 °C. In absorption spectra, HL-Me shows bands at 529 nm in the presence of Al3+. This metal ion turns the colorless solution of the probe to pink with Al3+. Other metal ions fail to produce any color change. HL-Me is almost non-fluorescent when it is excited at 500 nm. But, in the presence of Al3+, emission intensity at 552 nm increases massively. No other metal ion is able to cause significant enhancement of the emission intensity. HL-Me is colorless and non fluorescent due to the presence of spirolactam ring. Al3+ induces opening of the ring leading to the pink coloration and high fluorescence. Ring opening and subsequent complex formation with the metal ion have been confirmed by 1H, 13C NMR, IR and other spectral studies. LOD is determined to be 2.8 nM. Quantum yield and life-time of the probe enhance significantly upon complex formation with Al3+. HL-Me has been used for live cell imaging studies with different prokaryotic and eukaryotic cells. Reactions of L1 with salicyaldehyde with varying derivatives produce different rhodamine based probe for different analytes. An attempt has been made to categorize the probe based on the substituent present in it with metal ion selectivity.

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Publication details

The article was received on 08 Mar 2018, accepted on 30 Mar 2018 and first published on 02 Apr 2018


Article type: Paper
DOI: 10.1039/C8NJ01130C
Citation: New J. Chem., 2018, Accepted Manuscript
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    Rhodamine based fluorescent chemosensor for Al3+: Is it possible to control metal ion selectivity of rhodamine-6G based chemosensor?

    A. Roy, R. Mukherjee, B. Dam, S. Dam and P. Roy, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ01130C

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