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Original Articles

Synthesis and anion binding of 2-arylazo-meso-octamethylcalix[4]pyrroles

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Pages 394-400 | Received 28 Jan 2008, Accepted 11 Mar 2008, Published online: 30 Jun 2009
 

Abstract

2-Arylazo-5,5,10,10,15,15,20,20-octamethylcalix[4]pyrroles (azo-OMCPs) have been synthesised by the reaction of calix[4]pyrrole with aryldiazonium chloride in 15–45% yields. The solution-state binding studies of the synthesised hosts were investigated by absorption spectroscopy and 1H NMR in DMSO and CDCl3, respectively. These receptors, appended with electron-donating and electron-withdrawing groups, displayed enhanced affinity and selectivity for fluoride anion. Well-defined colour change in the visible region of the spectrum was observed upon addition of fluoride ion in DMSO solution of azo-OMCPs. Detailed NMR studies in CDCl3 revealed that azo-OMCPs with nitro and chloro groups have higher binding affinity for fluoride ion.

Acknowledgements

The authors are thankful to the Department of Science and Technology (DST) for project no. SR/S1/OC-54/2003, Council of Scientific and Industrial Research (CSIR) and University of Delhi, New Delhi, for their financial assistance.

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