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One-flask synthesis of mono- and trifunctionalized 21-thia and 21-oxaporphyrin building blocks and their application in the synthesis of covalent and noncovalent unsymmetrical porphyrin arrays.
MedLine Citation:
PMID:  15387605     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
A rapid synthetic route has been developed to synthesize mono- and trifunctionalized 21-thia and 21-oxaporphyrin systems using simple precursors such as 2[alpha-(aryl)-alpha-hydroxymethyl] thiophene (thiophene mono-ol) and 2[alpha-(aryl)-alpha-hydroxymethyl] furan (furan mono-ol), respectively. Condensation of one equivalent of thiophene or furan mono-ol with two equivalents of aryl aldehyde and three equivalents of pyrrole under porphyrin forming conditions followed by column chromatography resulted in functionalized 21-thia or 21-oxaporphyrins. To synthesize monofunctionalized porphyrins, the mono-ol containing the functionalized aryl group was used. The functionalized aldehydes were used to synthesize trifunctionalized porphyrins. The mono-ol method is versatile and applicable to synthesize mono- and trifunctionalized 21-thia and 21-oxaporphyrins containing functional groups such as iodophenyl, ethynylphenyl, hydroxyphenyl, bromophenyl, and pyridyl groups. The monofunctionalized porphyrin building blocks containing iodophenyl and ethynylphenyl groups were used further to synthesize four unsymmetrical covalent porphyrin dimers containing two different porphyrin cores such as N3S-N4, N3O-N4, and N3S-N3O bridged via diaryl ethyne group and one symmetrical phenylethyne bridged dimer containing two N3S cores. A preliminary photophysical study on these dimers indicated a possibility of energy transfer from one subunit to another. We also demonstrated the use of trifunctionalized porphyrins in the synthesis of two noncovalent unsymmetrical porphyrin tetramers containing one N3S and three N4 porphyrin subunits.
Authors:
Iti Gupta; Mangalampalli Ravikanth
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Oct 
Date Detail:
Created Date:  2004-09-24     Completed Date:  2005-05-11     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6796-811     Citation Subset:  -    
Copyright Information:
Copyright 2004 American Chemical Society
Affiliation:
Department of Chemistry, Indian Institute of Technology, Bomay, Powai, Mumbai 400 076, India.
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