Synthesis of an optically switchable salicylaldimine substituted naphthopyran for selective and reversible Cu2+ recognition in aqueous solution

Priya Ranjan Sahoo; Satish Kumar

doi:10.1039/C5RA24857D

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Synthesis of an optically switchable salicylaldimine substituted naphthopyran for selective and reversible Cu²⁺ recognition in aqueous solution†

Priya Ranjan Sahoo^a and Satish Kumar*^a

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* Corresponding authors

^a Department of Chemistry, St. Stephen’s College, University Enclave, Delhi – 110007, India
E-mail: satish@ststephens.edu

Abstract

A light controlled reversible switch for copper ion was synthesized by substituting photochromic naphthopyran with a salicylaldimine moiety. The naphthopyran based photoreversible receptor was characterized using IR, NMR, HRMS and single crystal X-ray crystallographic techniques. The photochromic properties of the receptor under light irradiation were investigated by UV-visible spectroscopy. The affinity towards transition metal ions in both closed and open forms were determined. The open form of the receptor displayed an increased affinity towards copper ions. A 3.25 × 10⁴ fold difference in binding affinity for copper ions between the closed and open forms in aqueous methanol solution suggested that the receptor can act as a selective photoswitch for copper ions. Theoretical investigations at the molecular level supported the experimental observations.

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DOI: https://doi.org/10.1039/C5RA24857D
Article type: Paper
Submitted: 23 Nov 2015
Accepted: 31 Jan 2016
First published: 01 Feb 2016

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RSC Adv., 2016,6, 20145-20154

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Synthesis of an optically switchable salicylaldimine substituted naphthopyran for selective and reversible Cu²⁺ recognition in aqueous solution

P. R. Sahoo and S. Kumar, RSC Adv., 2016, 6, 20145 DOI: 10.1039/C5RA24857D

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