Record Details

Synthesis, structure, and spectral, electrochemical and fluoride sensing properties of meso-pyrrolyl boron dipyrromethene

DSpace at IIT Bombay

View Archive Info
 
 
Field Value
 
Title Synthesis, structure, and spectral, electrochemical and fluoride sensing properties of meso-pyrrolyl boron dipyrromethene
 
Creator UMASEKHAR, B
GANAPATHI, E
CHATTERJEE, T
RAVIKANTH, M
 
Subject FLUORESCENT BODIPY DYES
NEAR-INFRARED NIR
SPECTROSCOPIC PROPERTIES
ENERGY-TRANSFER
FUNCTIONALIZED BORON
EFFICIENT SYNTHESIS
CHARGE-TRANSFER
SENSOR
PH
COMPLEXES
 
Description meso-Pyrrolyl boron dipyrromethene (BODIPY) was prepared under simple reaction conditions by using commercially available chemicals. Prior to this work, the BODIPY compound was prepared in multiple steps by using precursors which were not readily available. The X-ray structure of BODIPY revealed that the meso-pyrrole ring is tilted towards the BF2-dipyrrin moiety with a dihedral angle of 33.94 degrees. The reactivity of the meso-pyrrole ring of BODIPY was tested by subjecting it to bromination and formylation reactions, which afforded (alpha-bromopyrrolyl) BODIPY and (alpha-formylpyrrolyl) BODIPY in decent yields. The (alpha-formylpyrrolyl) BODIPY was used to prepare the pyrrole bridged BODIPY dyad. The pyrrole bridged BODIPY dyad exhibited a 15-20 nm bathochromic shift in the absorption band and was weakly fluorescent compared to meso-pyrrolyl BODIPY. Furthermore, our studies show that the meso-pyrrolyl BODIPY can be used as a specific sensor for F- ions because of the presence of meso-pyrrole NH which is involved in interactions with F- ions. To prove that meso-pyrrole NH is involved in sensing F- ions, we also prepared meso-(N-methylpyrrolyl)-BODIPY and characterized it by various spectroscopic techniques and crystallography. Our studies reveal that meso-(N-methylpyrrolyl)-BODIPY does not sense F- ions, supporting the involvement of meso-pyrrole NH in sensing F- ions.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2016-01-15T07:10:24Z
2016-01-15T07:10:24Z
2015
 
Type Article
 
Identifier DALTON TRANSACTIONS, 44(37)16516-16527
1477-9226
1477-9234
http://dx.doi.org/10.1039/c5dt02634b
http://dspace.library.iitb.ac.in/jspui/handle/100/18015
 
Language en