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Synthesis, Structure, and Hg2+-Ion-Sensing Properties of Stable Calixazasmaragdyrins

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Title Synthesis, Structure, and Hg2+-Ion-Sensing Properties of Stable Calixazasmaragdyrins
 
Creator CHATTERJEE, T
ARETI, S
RAVIKANTH, M
 
Subject EXPANDED PORPHYRIN
SAPPHYRIN
COMPLEXES
SMARAGDYRINS
TRANSPORT
BINDING
 
Description The first stable calixazasmaragdyrins containing two meso-sp(2) and one meso-sp(3) carbon atoms were synthesized by [3 + 2] condensation of 2,2'-(1-methylethylidene)bis-(pyrrole) and 5,10-diaryltripyrromethane under trifluoroacetic acid catalyzed conditions. The macrocycles were confirmed by high-resolution mass spectrometry, and the Molecular structures were deduced by detailed 1D and 2D NMR spectroscopy. The single-crystal structural analysis showed the highly strained and distorted nature of a calixazasmaragdyrin macrocycle. The presence of the one meso-sp(3) carbon center induces sufficient flexibility into the macro cycle, which, in turn, helps with the stability of the calixazasmaragdyrin macrocycle. The calixazasmargdyrins showed one broad absorption band at similar to 425 nm and an ill-defined band at similar to 685 nm. The electrochemical studies revealed that the calixazasmaragdyrins are not stable under redox conditions. Because the calixazasmargdyrin macrocyde possesses five pyrrole rings with three ionizable inner NH protons, we investigated anion and cation sensing properties of calixazasmargdyrins. Our studies revealed that the calixazasmaragdyrins do not show any sensing behavior toward anions but exhibited specific sensing behavior toward Hg2+ ions as verified by spectral and electrochemical studies.
 
Publisher AMER CHEMICAL SOC
 
Date 2016-01-15T06:25:06Z
2016-01-15T06:25:06Z
2015
 
Type Article
 
Identifier INORGANIC CHEMISTRY, 54(6)2885-2892
0020-1669
1520-510X
http://dx.doi.org/10.1021/ic503028k
http://dspace.library.iitb.ac.in/jspui/handle/100/17926
 
Language en