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Synthesis and Photophysical Properties of 3,5-Bis(oxopyridinyl)- and 3,5-Bis(pyridinyloxy)-Substituted Boron-Dipyrromethenes

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Title Synthesis and Photophysical Properties of 3,5-Bis(oxopyridinyl)- and 3,5-Bis(pyridinyloxy)-Substituted Boron-Dipyrromethenes
 
Creator KHAN, TK
RAO, MR
RAVIKANTH, M
 
Subject quantum-chemical calculations
fluorescent bodipy dyes
spectral properties
crystal-structure
lasing properties
charge-transfer
ph probes
derivatives
electrochemistry
solvent
boron
nitrogen heterocycles
dyes/pigments
fluorescence
fluorescent probes
photophysics
nucleophilic substitution
 
Description Nucleophilic substitution reactions of 2-, 3- and 4-hydroxy-pyridines with 3,5-dibromo meso-aryl and meso-furyl boron-dipyrromethenes (BODIPYs) resulted in the formation of the corresponding 3,5-bis(oxopyridinyl)-BODIPYs and 3,5-bis(pyridinyloxy)-BODIPYs in decent yields. The effect of a pyridone versus an oxypyridine at the 3- and 5-positions on the spectral, electrochemical and photophysical properties were studied as a function of solvent. The 3,5-bis(oxopyridinyl)- BODIPYs exhibit broad, red-shifted absorption and emission bands, decreased quantum yields and lifetimes, displayed large Stokes shifts and easier reductions than did the 3,5-bis(pyridinyloxy)-BODIPYs. The differences in the properties of these two classes of BODIPY dyes are attributed to the extension of pi-delocalization associated with the electron-deficient nature of the pyridone groups.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2011-09-01T21:08:57Z
2011-12-26T12:59:47Z
2011-12-27T05:52:41Z
2011-09-01T21:08:57Z
2011-12-26T12:59:47Z
2011-12-27T05:52:41Z
2010
 
Type Article
 
Identifier EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (12), 2314-2323
1434-193X
http://dx.doi.org/10.1002/ejoc.200901460
http://dspace.library.iitb.ac.in/xmlui/handle/10054/12868
http://hdl.handle.net/10054/12868
 
Language en