Record Details

Synthesis and Properties of Meso-unsubstituted 3-Pyrrolyl Boron Dipyrromethene

DSpace at IIT Bombay

View Archive Info
 
 
Field Value
 
Title Synthesis and Properties of Meso-unsubstituted 3-Pyrrolyl Boron Dipyrromethene
 
Creator LAKSHMI, V
SHAIKH, MS
RAVIKANTH, M
 
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
 
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.
 
Publisher SPRINGER/PLENUM PUBLISHERS
 
Date 2014-10-15T17:21:47Z
2014-10-15T17:21:47Z
2013
 
Type Article
 
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
 
Language en