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Synthesis, Structure, and Properties of Core-modified Pentaphyrins Containing Six meso Carbons

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Title Synthesis, Structure, and Properties of Core-modified Pentaphyrins Containing Six meso Carbons
 
Creator GANAPATHI, E
CHATTERJEE, T
LEE, WZ
RAVIKANTH, M
 
Subject EXPANDED PORPHYRIN
HEXAPYRROLE MACROCYCLES
ENHANCED TRANSPORT
ANION-BINDING
SAPPHYRIN
SMARAGDYRINS
PENTAPYRROLE
RECOGNITION
CARRIER
heterocycles
macrocycles
pentaphyrins
chemosensors
tripyrromethanes
 
Description Our successful synthesis of nonaromatic 24 core-modified pentaphyrins containing six meso carbons is reported. The pentaphyrins were prepared by [3+2] condensation of butane-2,3-diyl-bisthiophene-2,5-diyl-bis(p-methoxyphenylmethanol) with different meso-aryl tripyrromethanes under mild acid-catalyzed conditions. By using this method, we obtained two stable, core-modified pentaphyrins containing six meso carbons in acceptable yields. The pentaphyrins were characterized by HR-MS, 1D, 2D NMR, absorption and electrochemical techniques, and also by X-ray crystallography for one of the pentaphyrin macrocycles. The crystal structure revealed that the macrocycle is almost planar and one of the thiophene rings, which is positioned opposite to the ethene bridged meso-carbons, is inverted. Our studies revealed that the macrocycles in their protonated form have specific sensing ability for CH3COO- ions.
 
Publisher WILEY-V C H VERLAG GMBH
 
Date 2016-01-14T10:21:51Z
2016-01-14T10:21:51Z
2015
 
Type Article
 
Identifier ASIAN JOURNAL OF ORGANIC CHEMISTRY, 4(7)638-645
2193-5807
2193-5815
http://dx.doi.org/10.1002/ajoc.201500072
http://dspace.library.iitb.ac.in/jspui/handle/100/17358
 
Language en