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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

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Title 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
 
Creator GUPTA, I
RAVIKANTH, M
 
Subject light-harvesting arrays
energy-transfer processes
core-modified porphyrins
excited-state dynamics
electron-transfer
multiporphyrin arrays
coupling reactions
conjugated groups
appended systems
rational design
 
Description 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-N-4, 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 N-4 porphyrin subunits.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-14T14:23:33Z
2011-12-26T12:48:26Z
2011-12-27T05:38:08Z
2011-07-14T14:23:33Z
2011-12-26T12:48:26Z
2011-12-27T05:38:08Z
2004
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY, 69(20), 6796-6811
0022-3263
http://dx.doi.org/10.1021/jo040178u
http://dspace.library.iitb.ac.in/xmlui/handle/10054/3981
http://hdl.handle.net/10054/3981
 
Language en