Issue 3, 2010
From the journal:

Organic & Biomolecular Chemistry

Simple 1-dicyanomethylene-2-chloro-3-aminoindene push–pull chromophores: applications in cation and anion sensing†

Sara Basurto,a   Daniel Miguel,b   Daniel Moreno,a   Ana G. Neo,c   Roberto Quesadaa  and  Tomás Torroba*a  

* Corresponding authors

a Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Plaza Misael Bañuelos s/n, Burgos, Spain
E-mail: ttorroba@ubu.es
Fax: +34 947 258831
Tel: +34 947 258088

b Departamento de Química Física y Química Inorgánica, Facultad de Ciencias, Universidad de Valladolid, Valladolid, Spain
E-mail: dmsj@qi.uva.es
Fax: +34 983 423234
Tel: +34 983 184096

c Departamento de Química Orgánica, Facultad de Veterinaria, Universidad de Extremadura, Avenida de la Universidad s/n, Cáceres, Spain
E-mail: aneo@unex.es
Fax: +34 927 257110
Tel: +34 927 257158

Abstract

Push–pull chromophores based on 1-dicyanomethylene-2-chloro-3-aminoindene are readily synthesized. These compounds undergo dramatic colour changes in the presence of metal cations as a result of the interaction of the amino substituent with the analytes. One of these compounds is a selective copper(II) colorimetric probe in acetonitrile solution, displaying a dramatic colour change upon coordination of the amine group to the metal centre. These compounds are also selective cyanide sensors in acetonitrile solution because of the disruption of the intramolecular charge transfer process as the result of the nucleophilic addition of the anion to the indene moiety.

Graphical abstract: Simple 1-dicyanomethylene-2-chloro-3-aminoindene push–pull chromophores: applications in cation and anion sensing

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Article information

DOI
https://doi.org/10.1039/B916700E
Article type
Paper
Submitted
13 Aug 2009
Accepted
23 Oct 2009
First published
27 Nov 2009

Org. Biomol. Chem., 2010,8, 552-558

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Simple 1-dicyanomethylene-2-chloro-3-aminoindene push–pull chromophores: applications in cation and anion sensing

S. Basurto, D. Miguel, D. Moreno, A. G. Neo, R. Quesada and T. Torroba, Org. Biomol. Chem., 2010, 8, 552 DOI: 10.1039/B916700E

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