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Meso-functional calix[4]pyrrole: a solution phase study of anion directed self-assembly

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Abstract

The 5,10,10,15,15,20,20-heptamethyl-5(4′-phenylcarboxylate) calix[4]pyrrole allocates dimer formation in solution. The pattern of dimeric self-assembly was recognized by a combination of 1H NMR and mass spectrometry. The addition of F− perturbed this assembly pattern, owing to the selective formation of calixpyrrole–F− complex. Moreover, the spectroscopic findings revealed that calixpyrrole–F− complex further chelates to the pyrrolic core of other OMCP through carboxylate hook, serving as a secondary binding site.

Graphical Abstract

The 5,10,10,15,15,20,20-heptamethyl-5(4′-phenylcarboxylate) calix[4]pyrrole allocates dimer formation in solution. The pattern of dimeric self-assembly was recognized by a combination of 1H NMR and mass spectrometry. The addition of F− perturbed this assembly pattern, owing to the selective formation of calixpyrrole–F− complex. Moreover, the spectroscopic findings revealed that calixpyrrole–F− complex further chelates to the pyrrolic core of other OMCP through carboxylate hook, serving as a secondary binding site.

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Acknowledgments

The authors are thankful to the Department of Science and Technology (DST) for project number SR/S1/OC-54/2003, Council of Scientific and Industrial Research (CSIR) and University of Delhi, New Delhi for financial assistance.

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  1. Bhaskar Garg

    Present address: Department of Chemistry, National Tsing Hua University, Hsinchu, Taiwan, ROC

Authors and Affiliations

  1. Department of Chemistry, Bioorganic Research Laboratory, University of Delhi, Delhi, 110007, India

    Bhaskar Garg, Tanuja Bisht & Shive Murat Singh Chauhan

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  1. Bhaskar Garg
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  2. Tanuja Bisht
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Correspondence to Shive Murat Singh Chauhan.

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Garg, B., Bisht, T. & Chauhan, S.M.S. Meso-functional calix[4]pyrrole: a solution phase study of anion directed self-assembly. J Incl Phenom Macrocycl Chem 70, 249–255 (2011). https://doi.org/10.1007/s10847-010-9849-6

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