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Calix[4]arenes bearing a tropylium substituent as hosts for organic cations

  • M. Fehlinger
  • W. Abraham
Original Research Article

Abstract

Four novel calix[4]arenes bearing one cycloheptatrienyl substituent and two calix[4]arenes with one tropylium substituent at the wider rim were synthesized. Cycloheptatrienyl- and tropylium-calixarenes represent two states of a potentially photoswitchable calixarene host. The complexation of selected hosts with organic cations such as quinolinium, ammonium and tropylium ions was studied. It was found that the complexation of organic cations by the tropylium-substituted host was much stronger in CDCl3 solution than by the related cycloheptatrienyl-host. Aryltropylium ions are bound by tropylium hosts. Accordingly, dimers of the host itself are formed both in CDCl3 solution and in the gas phase. Because of the intramolecular charge transfer tropyliumcalix[4]arenes are qualified as chromogenic hosts. These undergo two acid-base equilibriums depending on the concentration and the solvent.

Keywords

Calix[4]arenes Cycloheptatriene Tropylium Complexation NMR-titration Isomeric complexes 

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Notes

Acknowledgements

Financial support by Deutsche Forschungsgemeinschaft is gratefully acknowledged. We thank Dr. B. Ziemer, HU Berlin, for the determination of the crystal structures.

Supplementary material

10847_2006_9153_MOESM1_ESM.doc (1.3 mb)
Supplementary material

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  1. 1.Institut für ChemieHumboldt-UniversitätBerlinGermany

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