Selective chromo-fluorogenic molecular sensor for dual channel recognition of Cu2+ and F−: effect of functional group on selectivity

Soumen Ghosh; Aniruddha Ganguly; Arghyadeep Bhattacharyya; Md. Akhtarul Alam; Nikhil Guchhait

doi:10.1039/C6RA09877K

Selective chromo-fluorogenic molecular sensor for dual channel recognition of Cu²⁺ and F⁻: effect of functional group on selectivity†

Soumen Ghosh,^a Aniruddha Ganguly,^a Arghyadeep Bhattacharyya,^a Md. Akhtarul Alam*^b and Nikhil Guchhait*^a

* Corresponding authors

^a Department of Chemistry, University of Calcutta, 92, A.P.C. Road, Kolkata 700 009, India
E-mail: nguchhait@yahoo.com
Fax: +91-33-23519755
Tel: +91-33-23508386

^b Department of Chemistry, Aliah University, IIA/27, New Town, Kolkata-700 156, West Bengal, India
E-mail: alam_iitg@yahoo.com

Abstract

The sensor HNHCB (3-hydroxy-naphthalene-2-carboxylic acid (4-cyano-benzylidene)-hydrazide) comprises a –CONH– group, –OH group, –CH [double bond, length as m-dash] N– linkage and an electron withdrawing –CN group that can act as both an anion (fluoride) and a cation (copper) sensor by two distinct output modes. It can detect fluoride by naked eye color change and copper by fluorescence enhancement. Interestingly, the nature of the substituent in HNHCB has an effect on the selectivity. The detection limit can be as low as 160 nM for Cu²⁺ and 1.3 μM for F⁻. DFT calculations have been performed to demonstrate the structure of HNHCB and its copper complex. Biological applications of HNHCB have been evaluated in HEK 293 and it was found to exhibit membrane permeability for the detection of Cu²⁺. The sensor HNHCB is also sensitive towards fluoride in commercially available toothpaste.

This article is part of the themed collection: Editors Collection for RSC Advances - India

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Article information

DOI: https://doi.org/10.1039/C6RA09877K
Article type: Paper
Submitted: 16 Apr 2016
Accepted: 27 Jun 2016
First published: 29 Jun 2016

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RSC Adv., 2016,6, 67693-67700

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Selective chromo-fluorogenic molecular sensor for dual channel recognition of Cu²⁺ and F⁻: effect of functional group on selectivity

S. Ghosh, A. Ganguly, A. Bhattacharyya, Md. A. Alam and N. Guchhait, RSC Adv., 2016, 6, 67693 DOI: 10.1039/C6RA09877K

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