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

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 64, Issue 3-4, 2009, Pages 367-371

  Ghera, Bernard Bertino ^a   Wu, Qiongzhi ^a   Leydier, Antoine ^a   Coleman, Anthony W ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

Calix 9 arene acylation; Calix n arene; Langmuir; Monolayer; Supramolecular assembly

Indexed keywords

EID: 70349682727     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-009-9561-6     Document Type: Article

References (18)

1. Gutsche, C.D.: Calixarenes Revisited. Royal Society of Chemistry, Cambridge, UK (1998).
2. Asfari, Z., Bohmer, V., Harrowfield, J., Vicens, J.: Calixarenes 2001, Chap. 4. Kluwer Academic Publishers, Dordrecht (2001).
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.
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.
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.
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.
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.
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.
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.
10. da Silva, E., Lazar, A.N., Coleman, A.W.: Biopharmaceutical applications of calixarenes. J. Drug Deliv. Sci. Technol. 14, 3-20 (2004).
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.
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.
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.
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.
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.
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.
17. 2+-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.
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.