Synthesis and Properties of Meso-unsubstituted 3-Pyrrolyl Boron Dipyrromethene
DSpace at IIT Bombay
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Title |
Synthesis and Properties of Meso-unsubstituted 3-Pyrrolyl Boron Dipyrromethene
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Creator |
LAKSHMI, V
SHAIKH, MS RAVIKANTH, M |
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Subject |
meso-free BODIPY
mes-free 3-pyrrolyl BODIPY Bright fluorescence High quantum yields Red shifted absorption and emission bands Large singlet-state lifetime BODIPY DYES CRYSTAL-STRUCTURE DERIVATIVES COMPLEXES ELECTROCHEMISTRY CHEMISTRY |
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Description |
We report the synthesis of meso-free 3-pyrrolyl boron dipyrrin (3-pyrrolyl BODIPY) and fully unsubstituted meso-free boron dipyrrin (parent BODIPY) in one pot under simple reaction conditions by treating meso-free dipyrromethane with pyrrole in CHCl3 followed by oxidation with DDQ, neutralization with triethylamine and complexation with BF3.OEt2. The compounds were separated by column chromatography on silica and isolated in 6-10 % yields. The compounds are characterized by HR-MS mass, NMR, absorption, electrochemical and fluorescence techniques. The meso-free 3-pyrrolyl BODIPY exhibit red shifted absorption and emission bands compared to meso-free BODIPY. The meso-free BODIPY exhibit green fluorescence and meso-free 3-pyrrolyl BODIPY exhibit orange fluorescence in solution. Furthermore, compared to meso-phenyl 3-pyrrolyl BODIPY, the meso-free 3-pyrrolyl BODIPY is more strongly fluorescent with nearly 41 % increase in quantum yield. Electrochemical studies showed that meso-free 3-pyrrolyl BODIPY exhibit one irreversible reduction and one ill-defined oxidation indicating that the compound is not stable under redox conditions. Computational studies revealed that meso-free pyrrolyl BODIPY has reduced HOMO-LUMO gap compared to parent meso-free BODIPY. Furthermore, the meso-free 3-pyrrolyl BODIPY exhibit much higher quantum yield compared to meso-aryl analogue of 3-pyrrolyl BODIPY.
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Publisher |
SPRINGER/PLENUM PUBLISHERS
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Date |
2014-10-15T17:21:47Z
2014-10-15T17:21:47Z 2013 |
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Type |
Article
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Identifier |
JOURNAL OF FLUORESCENCE, 23(3)519-525
http://dx.doi.org/10.1007/s10895-013-1165-2 http://dspace.library.iitb.ac.in/jspui/handle/100/15316 |
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Language |
en
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