Synthesis of Conjugated BODIPYs via the Wittig Reaction
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Title |
Synthesis of Conjugated BODIPYs via the Wittig Reaction
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Creator |
LAKSHMI, V
RAVIKANTH, M |
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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 |
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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.
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Publisher |
AMER CHEMICAL SOC
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Date |
2014-10-15T17:23:17Z
2014-10-15T17:23:17Z 2013 |
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Type |
Article
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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 |
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Language |
en
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