Strong intramolecular charge-transfer effect strengthening naphthoquinone-based chemosensor: Experimental and theoretical evaluation.
Spectrochim Acta A Mol Biomol Spectrosc
; 311: 123908, 2024 Apr 15.
Article
em En
| MEDLINE
| ID: mdl-38330753
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 Sn2+ ion in aqueous solution. The amine and conversion of carbonyl into carboxyl groups play a vital role in the sensing mechanism when Sn2+ 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 Sn2+ was observed at about 435 nm. The chemosensor exhibited good selectivity for Sn2+ in the presence of coexisting metal ions. An improved linear connection was established with a low limit of detection (0.167 µM). FT-IR, 1H NMR, 13C 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 Sn2+ in human cancer cells.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Spectrochim Acta A Mol Biomol Spectrosc
Assunto da revista:
BIOLOGIA MOLECULAR
Ano de publicação:
2024
Tipo de documento:
Article
País de publicação:
Reino Unido