Selective and swift-responsive “off-on” rhodamine B based chemosensors: Recognition of multi-metal ions, on-site sensing of Fe(III) in water samples and bioimaging in aqueous media

[Display omitted] •Distinct “off–on” rhodamine B based chemosensors for sensing and bioimaging.•High selectivity towards Fe+3 and naked eye detection in 

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Published in:Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2022-04, Vol.426, p.113748, Article 113748
Main Authors: Battula, Himabindu, Muduli, Sunita, Priyanka Bandi, Sony, Kapoor, Shristy, Mishra, Sabyashachi, Aggarwal, Himanshu, Vamsi krishna Venuganti, Venkata, Jayanty, Subbalakshmi
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Language:English
Subjects:
Bio-imaging of AGS cells
Chemosensors
Crystal structure
Rhodamine derivatives
Selective Fe(III) sensing
TD-DFT method
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cited_by cdi_FETCH-LOGICAL-c318t-ff503cddff632f4bdabe606aa8718c17822b1cfb2a967ef0a8028af602ab1abd3
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container_title Journal of photochemistry and photobiology. A, Chemistry.
container_volume 426
creator Battula, Himabindu
Muduli, Sunita
Priyanka Bandi, Sony
Kapoor, Shristy
Mishra, Sabyashachi
Aggarwal, Himanshu
Vamsi krishna Venuganti, Venkata
Jayanty, Subbalakshmi
description [Display omitted] •Distinct “off–on” rhodamine B based chemosensors for sensing and bioimaging.•High selectivity towards Fe+3 and naked eye detection in 
doi_str_mv 10.1016/j.jphotochem.2021.113748
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Distinct “off–on” rhodamine B based chemosensors 3',6'-bis(diethylamino)-2-(2-(diethylamino)ethyl) spiro[isoindoline-1,9′-xanthen]-3-one (2a); 3′,6′-bis(diethylamino)-2-(2-(dimethylamino)ethyl) spiro[isoindole-1,9′-xanthen]- 3-one (2b) are synthesized in a facile single-step reaction and characterized by X-ray crystallography, NMR, Mass, and FT-IR techniques. 2a, 2b; selectively detected Fe+3, Sn+2, and Cr+3, in aqueous media over 17 other environmentally relevant cations. Furthermore, 2a, 2b showed high selectivity towards Fe+3 ion with ∼ 62 fold (2a), ∼21 fold (2b) enhanced emission intensity. A prominent pink color, in &lt; 1 min (∼40 s) was detected under naked eye on sensing Fe+3. Enhanced emission was rationalized by natural transition orbital analysis using DFT and TD-DFT methods. Detection limit and binding constant of Fe+3 for 2a and 2b are estimated as 51.25 ppb (73 nM), 40.3 ppb (59.7 nM), and 0.80 × 103 M−1, 4.59 × 103 M−1, each respectively, indicating their efficiency towards Fe+3 sensing. A test strip method was developed for the on-site qualitative detection of target metal ions, and practical applicability was demonstrated by determining the concentration of Fe+3 ion in real water samples. Probes 2a, 2b further tested in human gastric adenocarcinoma (AGS) cell-lines via in-vitro imaging. 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A, Chemistry.</title><description>[Display omitted] •Distinct “off–on” rhodamine B based chemosensors for sensing and bioimaging.•High selectivity towards Fe+3 and naked eye detection in &lt; 1 min.•Enhanced fluorescence rationalized by DFT and TD-DFT methods for Fe+3 sensing.•2a, 2b possess potential application in real water samples and in-vitro imaging. Distinct “off–on” rhodamine B based chemosensors 3',6'-bis(diethylamino)-2-(2-(diethylamino)ethyl) spiro[isoindoline-1,9′-xanthen]-3-one (2a); 3′,6′-bis(diethylamino)-2-(2-(dimethylamino)ethyl) spiro[isoindole-1,9′-xanthen]- 3-one (2b) are synthesized in a facile single-step reaction and characterized by X-ray crystallography, NMR, Mass, and FT-IR techniques. 2a, 2b; selectively detected Fe+3, Sn+2, and Cr+3, in aqueous media over 17 other environmentally relevant cations. Furthermore, 2a, 2b showed high selectivity towards Fe+3 ion with ∼ 62 fold (2a), ∼21 fold (2b) enhanced emission intensity. A prominent pink color, in &lt; 1 min (∼40 s) was detected under naked eye on sensing Fe+3. Enhanced emission was rationalized by natural transition orbital analysis using DFT and TD-DFT methods. Detection limit and binding constant of Fe+3 for 2a and 2b are estimated as 51.25 ppb (73 nM), 40.3 ppb (59.7 nM), and 0.80 × 103 M−1, 4.59 × 103 M−1, each respectively, indicating their efficiency towards Fe+3 sensing. A test strip method was developed for the on-site qualitative detection of target metal ions, and practical applicability was demonstrated by determining the concentration of Fe+3 ion in real water samples. Probes 2a, 2b further tested in human gastric adenocarcinoma (AGS) cell-lines via in-vitro imaging. 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A, Chemistry.</jtitle><date>2022-04-01</date><risdate>2022</risdate><volume>426</volume><spage>113748</spage><pages>113748-</pages><artnum>113748</artnum><issn>1010-6030</issn><eissn>1873-2666</eissn><abstract>[Display omitted] •Distinct “off–on” rhodamine B based chemosensors for sensing and bioimaging.•High selectivity towards Fe+3 and naked eye detection in &lt; 1 min.•Enhanced fluorescence rationalized by DFT and TD-DFT methods for Fe+3 sensing.•2a, 2b possess potential application in real water samples and in-vitro imaging. Distinct “off–on” rhodamine B based chemosensors 3',6'-bis(diethylamino)-2-(2-(diethylamino)ethyl) spiro[isoindoline-1,9′-xanthen]-3-one (2a); 3′,6′-bis(diethylamino)-2-(2-(dimethylamino)ethyl) spiro[isoindole-1,9′-xanthen]- 3-one (2b) are synthesized in a facile single-step reaction and characterized by X-ray crystallography, NMR, Mass, and FT-IR techniques. 2a, 2b; selectively detected Fe+3, Sn+2, and Cr+3, in aqueous media over 17 other environmentally relevant cations. Furthermore, 2a, 2b showed high selectivity towards Fe+3 ion with ∼ 62 fold (2a), ∼21 fold (2b) enhanced emission intensity. A prominent pink color, in &lt; 1 min (∼40 s) was detected under naked eye on sensing Fe+3. Enhanced emission was rationalized by natural transition orbital analysis using DFT and TD-DFT methods. Detection limit and binding constant of Fe+3 for 2a and 2b are estimated as 51.25 ppb (73 nM), 40.3 ppb (59.7 nM), and 0.80 × 103 M−1, 4.59 × 103 M−1, each respectively, indicating their efficiency towards Fe+3 sensing. A test strip method was developed for the on-site qualitative detection of target metal ions, and practical applicability was demonstrated by determining the concentration of Fe+3 ion in real water samples. Probes 2a, 2b further tested in human gastric adenocarcinoma (AGS) cell-lines via in-vitro imaging. The increased emission intensity in 2a, 2b on binding to Fe+3 in AGS cells indicate their potentiality as small-molecule based biological fluorescent probes.</abstract><pub>Elsevier B.V</pub><doi>10.1016/j.jphotochem.2021.113748</doi></addata></record>
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subjects Bio-imaging of AGS cells
Chemosensors
Crystal structure
Rhodamine derivatives
Selective Fe(III) sensing
TD-DFT method
title Selective and swift-responsive “off-on” rhodamine B based chemosensors: Recognition of multi-metal ions, on-site sensing of Fe(III) in water samples and bioimaging in aqueous media
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