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Issue 28, 2014
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Boron-dipyrromethene based multi-anionic sensor and a specific cationic sensor for Fe3+

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Abstract

Symmetrical and unsymmetrical phenylhydrazone substituted boron-dipyrromethenes were synthesized by treating 3,5-diformyl boron-dipyrromethene with phenylhydrazine/2,4-dinitrophenylhydrazine in ethanol at reflux temperature. The X-ray structure of the unsymmetrical boron-dipyrromethene (BODIPY) was shown to have an almost extended planar orientation of BODIPY with 2,4-dinitrophenylhydrozone unit at the 3-position and ethyl acetal at the 5-position with small torsional angles. A strong absorption band at ∼600 to 700 nm and a weak emission band at ∼620 to 710 nm were observed for the phenylhydrazone substituted BODIPYs. The compounds showed interesting absorption properties in DMSO and DMF solvents compared to other solvents by shifting ∼150 nm towards the red region. Anion binding studies indicated that the unsymmetrical phenylhydrazone substituted BODIPY could be applied as a sensor for F, CH3COO and H2PO4 ions as confirmed by various spectroscopic studies. Furthermore, the unsymmetrical phenylhydrazone substituted BODIPY had the unique ability of acting as a two step fluorescence enhanced chemodosimetric sensor for Fe3+ ion.

Graphical abstract: Boron-dipyrromethene based multi-anionic sensor and a specific cationic sensor for Fe3+

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Supplementary files

Article information


Submitted
17 Feb 2014
Accepted
14 Mar 2014
First published
14 Mar 2014

J. Mater. Chem. C, 2014,2, 5576-5586
Article type
Paper

Boron-dipyrromethene based multi-anionic sensor and a specific cationic sensor for Fe3+

V. Lakshmi and M. Ravikanth, J. Mater. Chem. C, 2014, 2, 5576
DOI: 10.1039/C4TC00317A

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