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Issue 9, 2015
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meso-Salicylaldehyde substituted BODIPY as a chemodosimetric sensor for cyanide anions

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Abstract

The meso-salicylaldehyde substituted BODIPY was synthesized over a sequence of steps and characterized by X-ray crystallography, mass, NMR, absorption, fluorescence and electrochemical techniques. The crystal structure showed the presence of strong intramolecular hydrogen bonding between hydroxyl and formyl groups, which induces rigidity in the BODIPY core and makes the BODIPY relatively more fluorescent than the meso-phenyl BODIPY. Our studies showed that the meso-salicylaldehyde BODIPY can be used as a specific chemidosimetric sensor for CN ions. The presence of a hydroxyl group adjacent to a formyl group helps in activating the formyl group for a nucleophilic attack. Upon addition of the CN ion to the meso-salicylaldehyde BODIPY, the CN ion attacks the formyl group and converts it to the cyanohydrin group. This irreversible reaction was monitored by following the changes in absorption, fluorescence and electrochemical properties and the results support the view that the meso-salicylaldehyde substituted BODIPY can be used as a specific chemodosimetric sensor for CN ions. To substantiate the role of the hydroxyl group, we also prepared the meso(m-formylphenyl) BODIPY which contains only the formyl group on meso-phenyl, and our studies indicated that the meso(m-formylphenyl) BODIPY cannot be used as a chemodosimetric sensor for CN ions, as verified by absorption and emission studies.

Graphical abstract: meso-Salicylaldehyde substituted BODIPY as a chemodosimetric sensor for cyanide anions

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Supplementary files

Article information


Submitted
20 Nov 2014
Accepted
13 Jan 2015
First published
14 Jan 2015

Dalton Trans., 2015,44, 4054-4062
Article type
Paper

meso-Salicylaldehyde substituted BODIPY as a chemodosimetric sensor for cyanide anions

A. Dvivedi, P. Rajakannu and M. Ravikanth, Dalton Trans., 2015, 44, 4054
DOI: 10.1039/C4DT03568B

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