Synthesis and Photophysical Properties of 3,5-Bis(oxopyridinyl)- and 3,5-Bis(pyridinyloxy)-Substituted Boron-Dipyrromethenes
DSpace at IIT Bombay
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Title |
Synthesis and Photophysical Properties of 3,5-Bis(oxopyridinyl)- and 3,5-Bis(pyridinyloxy)-Substituted Boron-Dipyrromethenes
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Creator |
KHAN, TK
RAO, MR RAVIKANTH, M |
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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 |
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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.
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Publisher |
WILEY-V C H VERLAG GMBH
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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 |
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Type |
Article
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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 |
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Language |
en
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