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Synthesis, Spectral, Electrochemical, and Anion Binding Properties of 3,5-Bis(Dipyrromethanyl) Boron-Dipyrromethenes

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Title Synthesis, Spectral, Electrochemical, and Anion Binding Properties of 3,5-Bis(Dipyrromethanyl) Boron-Dipyrromethenes
 
Creator MADHU, S
RAVIKANTH, M
 
Subject QUANTUM-CHEMICAL CALCULATIONS
FLUORESCENT BODIPY DYES
ENERGY-TRANSFER
SPECTROSCOPIC PROPERTIES
FUNCTIONALIZED BORON
CRYSTAL-STRUCTURE
FLUORIDE IONS
RECEPTOR
SENSORS
RECOGNITION
 
Description Four new boron-dipyrromethenes (BODIPYs) containing dipyrromethanyl substituents at 3,5-positions, bis(3,5-dipyrromethanyl) BODIPYs 5-8, were synthesized by treating their corresponding 3,5-diformyl BODIPYs 1-4 with excess pyrrole under mild acid catalyzed reaction conditions. The compounds 5-8 are stable and freely soluble in common organic solvents. One-dimensional, two-dimensional NMR, high resolution mass spectrometry (HRMS), absorption, fluorescence, and electrochemical techniques were used to characterize the compounds. The spectral and electrochemical studies indicated that dipyrromethanyl groups at 3,5-positions of BODIPY are less electron deficient compared to formyl groups at the same positions. The anion binding studies indicated that bis(3,5-dipyrromethanyl) BODIPY compounds containing four pyrrole NH groups showed preferential binding with F ion over other anions, as confirmed by using NMR, fluorescence, and electrochemical studies.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-10-15T17:09:15Z
2014-10-15T17:09:15Z
2012
 
Type Article
 
Identifier INORGANIC CHEMISTRY, 51(7)4285-4292
http://dx.doi.org/10.1021/ic202758r
http://dspace.library.iitb.ac.in/jspui/handle/100/15291
 
Language en