Issue 17, 2019

Facile synthesis of mixed O, S or Se bearing hexasubstituted benzenes and their potential as Cu(ii) ion probe

Abstract

The present study offers a facile route for the synthesis of unsymmetrical hexasubstituted benzenes bearing alternate heteroatoms (O, S and Se) with the formula [1,3,5-(RSeCH2)3-2,4,6-(R′ECH2)3C6] (E = O, S or Se). The synthetic protocol involves the use of an in situ generated tris(selenonium) ion followed by treatment with another nucleophile affording the targeted species in >70% yields. The unsymmetrical hexasubstituted derivatives were characterized on the basis of physicochemical and spectroscopic data and in a representative case with single crystal X-ray study. The current work assumes great significance as the potential of these species as “turn-off” chemical sensors for Cu2+, which is a biologically and environmentally crucial metal ion, was also successfully demonstrated by 5a which bears alternate oxygen and selenium centres.

Graphical abstract: Facile synthesis of mixed O, S or Se bearing hexasubstituted benzenes and their potential as Cu(ii) ion probe

Supplementary files

Article information

Article type
Paper
Submitted
31 yan 2019
Accepted
26 mar 2019
First published
27 mar 2019

Dalton Trans., 2019,48, 5627-5636

Facile synthesis of mixed O, S or Se bearing hexasubstituted benzenes and their potential as Cu(II) ion probe

A. Kumar, M. K. Yadav, J. Singh, J. D. Singh and R. J. Butcher, Dalton Trans., 2019, 48, 5627 DOI: 10.1039/C9DT00465C

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