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Functionalization and Application of Calixarenes

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Molecular Engineering for Advanced Materials

Part of the book series: NATO ASI Series ((ASIC,volume 456))

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Abstract

Selectively functionalized calix[4]arenes are used to build effective receptors for cations, anions and neutral molecules or for a combination of a cation and an anion. This was done by combination with a terphenyl unit (cation receptor), a uranyl-containing salen moiety (for anionic and neutral guests) or by introduction of sulfonamide groups (anion receptor). Conformational control is effected using the appropriate conditions for the lower rim alkylation, but the conformation can also be influenced by hydrogen bonding. New routes for the synthesis of selectively functionalized calix[4]arenes bearing a combination of functional groups at the upper rim were developed together with a simple method for the direct introduction of meta substituents. Nitrated calix[4]arenes have very good non-linear optical characteristics. Selective methylation and phosphorylation of p-tert-butylcalix[6]arene is shown to be possible when specific conditions are used. The conformational properties of selectively functionalized calix[6]arenes were studied by 1H NMR spectroscopy. The controlled conformation of 1,3,5-trimethoxy-p-tert-butylcalix[6]arene was used to synthesize a cryptocalix[6]arene.

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Authors and Affiliations

  1. Laboratory of Organic Chemistry, University of Twente, P.O. Box 217, 7500 AE, Enschede, The Netherlands

    W. Verboom, R. H. Vreekamp, D. M. Rudkevich & D. N. Reinhoudt

Authors
  1. W. Verboom
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  2. R. H. Vreekamp
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  3. D. M. Rudkevich
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  4. D. N. Reinhoudt
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Editors and Affiliations

  1. Department of Chemistry, University of Odense, Campusvej 55, DK-5230, Odense M, Denmark

    Jan Becher

  2. CISMI, Department of Chemistry, University of Copenhagen, Fruebjergvej 3, DK-2100, Copenhagen, Denmark

    Kjeld Schaumburg

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© 1995 Springer Science+Business Media Dordrecht

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Verboom, W., Vreekamp, R.H., Rudkevich, D.M., Reinhoudt, D.N. (1995). Functionalization and Application of Calixarenes. In: Becher, J., Schaumburg, K. (eds) Molecular Engineering for Advanced Materials. NATO ASI Series, vol 456. Springer, Dordrecht. https://doi.org/10.1007/978-94-015-8575-0_7

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  • DOI: https://doi.org/10.1007/978-94-015-8575-0_7

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-90-481-4521-8

  • Online ISBN: 978-94-015-8575-0

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