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Synthesis and Studies of Thiacorroles

DSpace at IIT Bombay

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Title Synthesis and Studies of Thiacorroles
 
Creator SHETTI, VS
PRABHU, UR
RAVIKANTH, M
 
Subject core-modified corroles
free-base corroles
photophysical properties
porphyrin arrays
1st examples
complexes
electrochemistry
spectroelectrochemistry
cyclopropanation
dipyrromethanes
 
Description The first examples of stable 22-thiacorroles containing a direct pyrrole pyrrole bond were synthesized using thiophene monocarbinols as key precursors. Condensation of 1 equiv of thiophene monocarbinol with 1 equiv of substituted aldehyde and 1.5 equiv of pyrrole under refluxing propionic acid conditions followed by alumina column chromatographic purification yielded the desired 22-thiacorroles. Although the corrole formation had been observed with variety of substituted aldehydes, the stable thiacorroles were isolated in 2-3% yields only with 4- and 3-nitrobenzaldehydes. The stable thiacorroles were obtained only under harsh propionic acid conditions and any other mild reaction conditions did not yield 22-thiacorroles. The structure of thiacorroles were unambiguously established using mass, and ID and 2D NMR spectroscopy. The NMR study indicated diminished ring current and distortion of 22-thiacorroles. DFT studies also supported the distortion of thiacorroles. The absorption spectra showed reduction in number of absorption bands and fluorescence study indicated that 22-thiacorroles are weakly fluorescent. The electrochemical studies indicated that 22-thiacorroles undergo easier reductions compared to thiaporphyrins.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-15T00:13:35Z
2011-12-26T12:49:08Z
2011-12-27T05:34:53Z
2011-07-15T00:13:35Z
2011-12-26T12:49:08Z
2011-12-27T05:34:53Z
2010
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 75(12), 4172-4182
0022-3263
http://dx.doi.org/10.1021/jo100607t
http://dspace.library.iitb.ac.in/xmlui/handle/10054/4102
http://hdl.handle.net/10054/4102
 
Language en