Para-acyl-calix[9]arenes: synthesis and interfacial assembly

  • Bernard Bertino Ghera
  • Qiongzhi Wu
  • Antoine Leydier
  • Anthony W. Coleman


The synthesis of a series of five para-acyl-calix[9]arenes has been achieved with total substitution as shown by MALDI-TOF mass spectrometry. All compounds form stable monolayers at the air–water interface, with apparent molecular areas between 200 and 330 Å2.


Calix[n]arene Calix[9]arene acylation Langmuir Monolayer Supramolecular assembly 



The research was supported by the Centre National de la Recherche Scientifique (CNRS), ANR (PCV) program and the Université Claude Bernard Lyon 1 (UCBL).


  1. 1.
    Gutsche, C.D.: Calixarenes Revisited. Royal Society of Chemistry, Cambridge, UK (1998)Google Scholar
  2. 2.
    Asfari, Z., Bohmer, V., Harrowfield, J., Vicens, J.: Calixarenes 2001, Chap. 4. Kluwer Academic Publishers, Dordrecht (2001)Google Scholar
  3. 3.
    Shinkai, S., Nagasaki, T., Iwamoto, K., Ikeda, A., He, G.X., Matsuda, T., Iwamoto, M.: New syntheses and physical properties of p-alkylcalix[n]arenes. Bull. Chem. Soc. Jpn. 64, 381–386 (1991). doi: 10.1246/bcsj.64.381 CrossRefGoogle Scholar
  4. 4.
    Shahgaldian, P., Coleman, A.W., Kalchenko, V.I.: Synthesis and properties of novel amphiphilic calix-[4]-arene derivatives. Tetrehedron Lett 42, 577–579 (2001). doi: 10.1016/S0040-4039(00)02003-7 CrossRefGoogle Scholar
  5. 5.
    Ananchenko, G.S., Moudrakovski, I.L., Coleman, A.W., Ripmeester, J.A.: A channel-free soft-walled capsular calixarene solid for gas adsorption. Angew. Chem. Int. Ed. 47, 5616–5618 (2008). doi: 10.1002/anie.200800071 CrossRefGoogle Scholar
  6. 6.
    Coleman, A.W., Jebors, S., Shahgaldian, P., Ananchenko, G.S., Ripmeester, J.A.: para-acylcalix[n]arenes: from molecular to macroscopic assemblies. Chem. Commun. 20, 2291–2303 (2008). doi: 10.1039/b717495k CrossRefGoogle Scholar
  7. 7.
    Shahgaldian, P., Da Silva, E., Coleman, A.W., Rather, B., Zaworotko, M.J.: Para-acyl-calix-arene based solid lipid nanoparticles (SLNs): a detailed study of preparation and stability parameters. Int. J. Pharm. 253, 23–38 (2003). doi: 10.1016/S0378-5173(02)00639-7 CrossRefGoogle Scholar
  8. 8.
    Jebors, S., Ananchenko, G.S., Coleman, A.W., Ripmeester, J.A.: Synthesis and self-assembly properties of para-acyl-calix[8]arenes. Tetrahedron Lett. 48, 5503–5506 (2007). doi: 10.1016/j.tetlet.2007.05.169 CrossRefGoogle Scholar
  9. 9.
    Jebors, S., Fache, F., Balme, S., Devoge, F., Monachino, M., Cecillon, S., Coleman, A.W.: Designer amphiphiles based on para-acyl-calix[8]arenes. Org. Biomol. Chem. 6, 319–329 (2008). doi: 10.1039/b713883k CrossRefGoogle Scholar
  10. 10.
    da Silva, E., Lazar, A.N., Coleman, A.W.: Biopharmaceutical applications of calixarenes. J. Drug Deliv. Sci. Technol. 14, 3–20 (2004)Google Scholar
  11. 11.
    Perret, F., Lazar, A.N., Coleman, A.W.: Biochemistry of the para-sulfonato-calix[n]arenes. Chem. Commun. 23, 2425–2438 (2006). doi: 10.1039/b600720c CrossRefGoogle Scholar
  12. 12.
    Dumazet, I., Regnouf-De-Vains, J.-B., Lamartine, R.: Synthesis and characterization of p-tert-butyl-calix[9, 10, 11 and 12]arenes. Synth. Commun. 27, 2547–2555 (1997). doi: 10.1080/00397919708004122 CrossRefGoogle Scholar
  13. 13.
    Stewart, D.R., Gutsche, C.D.: Isolation, characterization, and conformational characteristics of p-tert-butylcalix[9–20]arenes. J. Am. Chem. Soc. 121, 4136–4146 (1999). doi: 10.1021/ja983964n CrossRefGoogle Scholar
  14. 14.
    Bouoit-Montesinos, S., Vocanson, F., Bassus, J., Lamartine, R.: Synthesis of new calix[9]arenes. Synth. Commun. 30, 911–915 (2000). doi: 10.1080/00397910008087104 CrossRefGoogle Scholar
  15. 15.
    Gloede, J., Ozegowski, S., Costisella, B., Gutsche, C.D.: Threefold bridged p-tert-butylcalix[9]arene triphosphate. Eur. J. Org. Chem. 24, 4870–4873 (2003). doi: 10.1002/ejoc.200300208 CrossRefGoogle Scholar
  16. 16.
    Fleming, S., Gutsche, C.D., Harrowfield, J.M., Ogden, M.I., Skelton, B.W., Stewart, D.F., White, A.H.: Calixarenes as aryloxides: oligonuclear europium(III) derivatives. Dalton Trans. 17, 3319–3327 (2003). doi: 10.1039/b305041f CrossRefGoogle Scholar
  17. 17.
    Mlika, R., Dumazet, I., Ouada, H.B., Jaffrezic-Renault, N., Lamartine, R., Gamoudi, M., Guillaud, G.: Cu2+-ISFET type microsensors based on thermally evaporated p-tert-butylcalix[9 and 11]arene thin films. Sens. Actuators B Chem. B62, 8–12 (2000). doi: 10.1016/S0925-4005(99)00355-X CrossRefGoogle Scholar
  18. 18.
    Bew, S.P., Sharma, S.V.: An expedient one-pot synthesis of para-tert-butylcalix[8]- and [9]arene. Chem. Commun. 9, 975–977 (2007). doi: 10.1039/b608482f CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2009

Authors and Affiliations

  • Bernard Bertino Ghera
    • 1
  • Qiongzhi Wu
    • 1
  • Antoine Leydier
    • 1
  • Anthony W. Coleman
    • 1
  1. 1.Institut de Biologie et Chimie des Protéines, CNRS-UMR 5086Université Lyon 1Lyon Cedex 07France

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