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Synthesis and electronic properties of meso-furyl boron dipyrromethenes

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Title Synthesis and electronic properties of meso-furyl boron dipyrromethenes
 
Creator KHAN, TK
JANA, SK
RAO, MR
SHAIKH, MS
RAVIKANTH, M
 
Subject Meso-furyl boron dipyrromethene
Hydrogen bonding
Dihedral angle
Stoke's shift
Easier reductions
FLUORESCENT BODIPY DYES
CHARGE-TRANSFER
ELECTROGENERATED CHEMILUMINESCENCE
CRYSTAL-STRUCTURE
PHOTOPHYSICS
SYSTEMS
ELECTROCHEMISTRY
SUBSTITUTION
SPECTROSCOPY
CHEMOSENSOR
 
Description Four meso-furyl boron-dipyrromethenes (BODIPYs) were synthesized and characterized. The X-ray structures solved for three meso-furyl BODIPYs indicated the presence of an intramolecular hydrogen bond between meso-furyl 'O' and 'H' of boron-dipyrromethene core resulting in decrease of dihedral angle between the meso-furyl group and boron-dipyrromethene core leading to better electronic interaction. However, the hydrogen bonding is absent in solution as confirmed by NMR studies in different solvents. The presence of meso-furyl group alters the electronic properties of BODIPY which reflected in the down-field shifts in H-1 NMR, bathochromic shifts in absorption and emission bands compared to the meso-tolyl BODIPY. The electrochemical studies indicated that the meso-furyl BODIPYs are easier to reduce compared to meso-tolyl BODIPYs. DFT studies showed that the HOMO-LUMO energy gap is decreased in meso-furyl BODIPYs compared to meso-tolyl BODIPY which is in agreement with the experimental observations. (C) 2011 Elsevier B. V. All rights reserved.
 
Publisher ELSEVIER SCIENCE SA
 
Date 2014-10-16T06:39:39Z
2014-10-16T06:39:39Z
2012
 
Type Article
 
Identifier INORGANICA CHIMICA ACTA, 383257-266
http://dx.doi.org/10.1016/j.ica.2011.11.017
http://dspace.library.iitb.ac.in/jspui/handle/100/15456
 
Language en