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Synthesis of Conjugated BODIPYs via the Wittig Reaction

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Title Synthesis of Conjugated BODIPYs via the Wittig Reaction
 
Creator LAKSHMI, V
RAVIKANTH, M
 
Subject QUANTUM-CHEMICAL CALCULATIONS
SOLID POLYMERIC MATRICES
SENSITIZED SOLAR-CELLS
NEAR-INFRARED NIR
BORON DIPYRROMETHENE
ENERGY-TRANSFER
CRYSTAL-STRUCTURE
NUCLEOPHILIC-SUBSTITUTION
SPECTROSCOPIC PROPERTIES
PHOTODYNAMIC THERAPY
 
Description A Wittig reaction was employed to synthesize conjugated BODIPYs in high yields by treating formylated BODIPYs with alkyl/aryl ylides under simple room temperature conditions. Treatment of 3,5-diformyl BODIPYs or a-formyl 3-pyrrolyl BODIPY with different alkyl/aryl ylides in CH2Cl2 at room temperature for 2 h followed by straightforward column chromatographic purification on silica afforded conjugated BODIPYs in similar to 65-90% yields. This is an alternate method to Knoevenagel and Heck reactions which have been used to synthesize such conjugated BODIPYs. The method works very efficiently, and we prepared 12 substituted BODIPYs including cholesterol-substituted BODIPYs to demonstrate the versatility of the reaction. The spectral, electrochemical, and fluorescence properties of these conjugated BODIPYs are also described.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-10-15T17:23:17Z
2014-10-15T17:23:17Z
2013
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 78(10)4993-5000
http://dx.doi.org/10.1021/jo4006969
http://dspace.library.iitb.ac.in/jspui/handle/100/15319
 
Language en