Journal
INORGANICA CHIMICA ACTA
Volume 383, Issue -, Pages 257-266Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.ica.2011.11.017
Keywords
Meso-furyl boron dipyrromethene; Hydrogen bonding; Dihedral angle; Stoke's shift; Easier reductions
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Funding
- CSIR
- DST
- Indian Institute of Technology
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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.
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