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Issue 16, 2014
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Stable core-modified calixsmaragdyrins: synthesis, structure and specific sensing of the hydrogen sulfate ion

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Abstract

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 sp3meso-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 sp3meso-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.

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

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Publication details

The article was received on 06 Nov 2013, accepted on 24 Dec 2013 and first published on 03 Jan 2014


Article type: Paper
DOI: 10.1039/C3DT53134A
Citation: Dalton Trans., 2014,43, 6050-6058
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    Stable core-modified calixsmaragdyrins: synthesis, structure and specific sensing of the hydrogen sulfate ion

    T. Chatterjee, A. Ghosh, S. Madhu and M. Ravikanth, Dalton Trans., 2014, 43, 6050
    DOI: 10.1039/C3DT53134A

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