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Influence of structure on electrochemical reduction of isomeric mono- and di-, nitro- or nitrosocalix[4]arenes

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Abstract

A newly synthesized series of mono- and di-, nitro- or nitrosocalix[4]arenes has been investigated electrochemically. It was shown that besides the fundamental redox characterization, the electrochemical data contain also information about the space arrangement of the molecule as well as about dynamic 3D changes. The interpretation is based on the comparison of observed electrochemical behavior of homologous couples or triads taken from the studied series of compounds. Using the nitro and nitroso group as a redox probe, it was found that unsubstituted or para-nitro-substituted cone-calixarenes are flexible, exhibiting in solution a periodic pinched cone–pinched cone interconversion, whereas the 1,3-alt conformation or any meta-substitution causes rigidity of the whole skeleton. All aromatic nitro and nitroso groups in calixarenes appeared to be reducible at the same potential showing their electronic independency on the rest of the molecule.

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Acknowledgments

This work was supported by the GACR grant No. 13-21704S, institutional support RVO: 61388955 and GAUK project No. 798214. The authors thank Kateřina Vítková for technical assistance in the frame of the project ASCR Otevřená věda (Open Science).

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Authors and Affiliations

  1. Department of Molecular Electrochemistry, J. Heyrovský Institute of Physical Chemistry AS CR, Dolejškova 2155/3, 182 23, Prague 8, Czech Republic

    Alan Liška & Jiří Ludvík

  2. Department of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Albertov 6, 128 43, Prague 2, Czech Republic

    Alan Liška

  3. Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28, Prague 6, Czech Republic

    Karolína Flídrová & Pavel Lhoták

Authors
  1. Alan Liška
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  2. Karolína Flídrová
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  3. Pavel Lhoták
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  4. Jiří Ludvík
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Correspondence to Jiří Ludvík.

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Liška, A., Flídrová, K., Lhoták, P. et al. Influence of structure on electrochemical reduction of isomeric mono- and di-, nitro- or nitrosocalix[4]arenes. Monatsh Chem 146, 857–862 (2015). https://doi.org/10.1007/s00706-015-1441-8

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  • DOI: https://doi.org/10.1007/s00706-015-1441-8

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