Simultaneous Detection of Cu2+ and Hg2+ via Two Mutually Independent Sensing Pathways of Biimidazole Push-Pull Dye

Dey, N and Kulhánek, J and Bureš, F and Bhattacharya, S (2019) Simultaneous Detection of Cu2+ and Hg2+ via Two Mutually Independent Sensing Pathways of Biimidazole Push-Pull Dye. In: Journal of Organic Chemistry, 84 (4). pp. 1787-1796.

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Abstract

An easy-to-synthesize, biimidazole push-pull dye has been designed, comprising two mutually independent analyte binding sites. It has been found that Hg2+ coordinates with the compound via thiophene residue and inhibits the charge-transfer (CT) process, which transforms the yellow-colored solution colorless. On the other hand, an unusually large bathochromic shift is observed in CT band upon addition of Cu2+, accompanied by a change in the color from yellow to red. A rather surprising observation is made from mechanistic studies, where it indicates that Cu2+ catalyzes the formation of 6-imino-5,6-dihydropyrrolo3,4-dimidazole-4(3H)-one (IPIMO) derivative. This strongly affects the charge-transfer state of the compound as well as its polarizability. Most importantly, this is the first report where IPIMO formation reaction has been exploited for sensing of a metal ion. Further, the system was employed for screening of both of these metal ions in wastewater samples. Recovery values ranging from 93.3 to 105.0% confirm the suitability of the present method for estimating trace level of metal ions in complex matrices. In addition, inexpensive on-site detection systems were developed using paper strips. © 2018 American Chemical Society.

Item Type:	Journal Article
Publication:	Journal of Organic Chemistry
Publisher:	American Chemical Society
Additional Information:	The copyright for this article belongs to American Chemical Society
Keywords:	Binding sites; Charge transfer; Metal ions; Metals; Screening; Trace elements, Bathochromic shift; Charge transfer state; Formation reaction; Mechanistic studies; Mutually independents; On-site detection; Simultaneous detection; Wastewater samples, Metal recovery, 6 imino 5,6 dihydropyrrolo3,4 dimidazole 4(3h) one derivative; biimidazole push pull dye; cupric ion; dye; imidazole derivative; mercury; pyrrole derivative; thiophene; unclassified drug, Article; binding site; catalysis; charge transfer; chemical interaction; chemical parameters; chemical reaction; color; conjugate; controlled study; polarization; reaction analysis; stoichiometry; synthesis
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	13 Dec 2022 05:01
Last Modified:	13 Dec 2022 05:01
URI:	https://eprints.iisc.ac.in/id/eprint/78331

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