Strong intramolecular charge-transfer effect strengthening naphthoquinone-based chemosensor: Experimental and theoretical evaluation.

Spectrochim Acta A Mol Biomol Spectrosc

Department of Life Science, Jeonbuk National University, Jeonju, Jeollabuk-do 54896, Republic of Korea; Department of Energy Storage/Conversion Engineering of Graduate School (BK21 FOUR), Hydrogen and Fuel Cell Research Center, Jeonbuk National University, Jeonju, Jeollabuk-do 54896, Republic of Kor

Published: April 2024


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Article Abstract

An aminophenol-linked naphthoquinone-based fluorometric and colorimetric chemosensor 2-chloro-3-((3-hydroxyphenyl) amino) naphthalene-1,4-dione (2CAN-Dione) was synthesized for selective detection of Sn ion in aqueous solution. The amine and conversion of carbonyl into carboxyl groups play a vital role in the sensing mechanism when Sn is added to 2CAN-Dione. Comprehensive characterization of the sensor was carried out using standard spectral and analytical approaches. Because of the intramolecular charge transfer (ICT) effect and the turn-on sensing mode, the strong fluorometric emission towards Sn was observed at about 435 nm. The chemosensor exhibited good selectivity for Sn in the presence of coexisting metal ions. An improved linear connection was established with a low limit of detection (0.167 μM). FT-IR, H NMR, C NMR, and quantum chemistry methods were performed to verify the binding coordination mechanism. The chemosensing probe 2CAN-Dione was successfully employed in bioimaging investigations, demonstrating that it is a reliable fluorescent marker for Sn in human cancer cells.

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http://dx.doi.org/10.1016/j.saa.2024.123908DOI Listing

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