Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/xmlui/handle/100/17976
Title: meso-Salicylaldehyde substituted BODIPY as a chemodosimetric sensor for cyanide anions
Authors: DVIVEDI, A
RAJAKANNU, P
RAVIKANTH, M
Keywords: Selective Detection
Crystal-Structure
Aqueous-Media
Complexes
Water
Dyad
Ion
Issue Date: 2015
Publisher: ROYAL SOC CHEMISTRY
Citation: DALTON TRANSACTIONS, 44(9)4054-4062
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.
URI: http://dx.doi.org/10.1039/c4dt03568b
http://dspace.library.iitb.ac.in/jspui/handle/100/17976
ISSN: 1477-9226
1477-9234
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