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Stable core-modified calixsmaragdyrins: synthesis, structure and specific sensing of the hydrogen sulfate ion

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Title Stable core-modified calixsmaragdyrins: synthesis, structure and specific sensing of the hydrogen sulfate ion
 
Creator CHATTERJEE, T
GHOSH, A
MADHU, S
RAVIKANTH, M
 
Subject X-RAY-STRUCTURE
ANION-BINDING
MESO-ARYL
EXPANDED PORPHYRIN
CALIXPYRROLES
CALIXPHYRINS
SMARAGDYRINS
MACROCYCLES
RECEPTOR
COMPLEXES
 
Description Stable calixoxa- and calixthiasmaragdyrins containing three methine bridges and two direct bonds connecting the five pyrrole/heterocycle rings were synthesized by [3 + 2] condensation of dipyrromethane with 16-oxatripyrrane and 16-thiatripyrrane respectively under mild acid-catalyzed conditions. The compounds were characterized by HR-MS, 1D & 2D NMR, absorption and electrochemical techniques and the structure of calixoxasmaragdyrin was solved by X-ray crystallography. The crystal structure analysis indicated that the calixoxasmaragdyrin macrocycle was highly distorted due to the flexibility introduced by one sp(3) meso-carbon. The compounds show ill-defined absorption bands and irreversible oxidation and reduction waves which were attributed to the disruption of conjugation of the macrocycle by incorporation of one sp(3) meso-carbon. The anion binding studies indicated that the calixoxasmaragdyrin exhibited specific sensing ability for the HSO4- ion over other anions whereas calixthiasmaragdyrins did not even show an ability to bind anions.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-12-28T12:12:47Z
2014-12-28T12:12:47Z
2014
 
Type Article
 
Identifier DALTON TRANSACTIONS, 43(16)6050-6058
1477-9226
1477-9234
http://dx.doi.org/10.1039/c3dt53134a
http://dspace.library.iitb.ac.in/jspui/handle/100/16463
 
Language English