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Para-acylcalix[6]arenes: their synthesis, per-O-functionalisation, solid-state structures and interfacial assembly properties

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Abstract

The para-acylcalix[6]arenes bearing butanoyl, hexanoyl and octanoyl chains have been synthesized by Friedel–Crafts acylation of the parent calixarene. Persubstitution at the phenolic face was achieved to yield the methoxy-diethoxy, ethoxycarbonylmethoxy, methoxycarboxylic acid and butoxysulphonate derivatives. In the case of the derivatives, 5,11,17,23,29,35-hexa-octanoyl-37,38,39,40,41,42-hexa-methoxy-diethoxy-calix[6]arene, 5,11,17,23,29,35-hexa-butanoyl-37,38,39,40,41,42-hexaethoxycarbonyl methoxy-calix[6]arene and 5,11,17,23,29,35-hexa-octanoyl-37,38,39,40,41,42-hexaethoxycarbonyl methoxy-calix[6]arene the solid state structures were determined and show inclusion of two ester groups in the cavity. While for the para-acylcalix[6]arenes no stable monolayers can be formed at the air–water interface, stable monolayers are formed with the methoxy-diethoxy, ethoxycarbonylmethoxy, methoxycarboxylato compounds which show apparent molecular areas in the range 150–200 Å2 depending on the length of the acyl chains.

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Acknowledgements

This research was partially supported by the Polish Ministry of Science and Higher Education (Grant 401/ERA-NET/2009), and the DGA and CNRS.

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Authors and Affiliations

  1. Institut de Biologie et Chimie des Protéines, UMR 5086, CNRS, Université Lyon 1, 7 passage du Vercors, 69367, Lyon, France

    Said Jebors & Anthony W. Coleman

  2. Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka, 44/52, 01224, Warszawa, Poland

    Barbara Leśniewska, Oleksandr Shkurenko & Kinga Suwińska

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  1. Said Jebors
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  2. Barbara Leśniewska
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  3. Oleksandr Shkurenko
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  4. Kinga Suwińska
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  5. Anthony W. Coleman
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Correspondence to Anthony W. Coleman.

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Jebors, S., Leśniewska, B., Shkurenko, O. et al. Para-acylcalix[6]arenes: their synthesis, per-O-functionalisation, solid-state structures and interfacial assembly properties. J Incl Phenom Macrocycl Chem 68, 207–217 (2010). https://doi.org/10.1007/s10847-010-9769-5

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  • DOI: https://doi.org/10.1007/s10847-010-9769-5

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