Insights into the structure of the supramolecular amphiphile formed by a sulfonated calix[6]arene and alkyltrimethylammonium surfactants

Langmuir

Volumn 28, Issue 16, 2012, Pages 6561-6568

  Basilio, Nuno ^a   Martiin Pastor M ^a   García Río, Luis ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CALIX[6]ARENES; CROSS RELAXATION; DODECYLTRIMETHYLAMMONIUM BROMIDES; MACROCYCLES; SATURATION-TRANSFER DIFFERENCES; SUPRAMOLECULAR AMPHIPHILES;

AMMONIUM COMPOUNDS; BROMINE COMPOUNDS; CATIONIC SURFACTANTS; DYES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

SUPRAMOLECULAR CHEMISTRY;

EID: 84860174212     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la3006794     Document Type: Article

References (38)

1. Asfari, Z., Bohmer, V., Harrowfield, J., Vicens, J., Eds. Calixarenes 2001; Kluwer Academic Publishers: Dordrecht, The Netherlands, 2001.
2. Böhmer, V. Calixarenes, macrocycles with (almost) unlimited possibilities Angew. Chem., Int. Ed. Engl. 1995, 34, 713-745
3. Rebek, J. Host-guest chemistry of calixarene capsules Chem. Commun. 2000, 637-643 (Pubitemid 30225479)
4. Bogdan, A.; Rudzevich, Y.; Vysotsky, M. O.; Böhmer, V. Topologically novel multiple rotaxanes and catenanes based on tetraurea calix[4]arenes Chem. Commun. 2006, 2941-2952 (Pubitemid 44036417)
5. Shinkai, S.; Mori, S.; Koreishi, H.; Tsubaki, T.; Manabe, O. Hexasulfonated calix[6]arene derivatives: a new class of catalysts, surfactants, and host molecules J. Am. Chem. Soc. 1986, 108, 2409-2416
6. Strobel, M.; Kita-Tokarczyk, K.; Taubert, A.; Vebert, C.; Heiney, P. A.; Chami, M.; Meier, W. Self-assembly of amphiphilic calix[4]arenes in aqueous solution Adv. Funct. Mater. 2006, 16, 252-259 (Pubitemid 43112702)
7. Kellermann, M.; Bauer, W.; Hirsch, A.; Schade, B.; Ludwig, K.; Bottcher, C. The first account of a structurally persistent micelle Angew. Chem., Int. Ed. 2004, 43, 2959-2962 (Pubitemid 39257655)
8. Lee, M.; Lee, S. J.; Jiang, L. H. Stimuli-responsive supramolecular nanocapsules from amphiphilic calixarene assembly J. Am. Chem. Soc. 2004, 126, 12724-12725 (Pubitemid 39372272)
9. Houmadi, S.; Coquière, D.; Legrand, L.; Fauré, M. C.; Goldmann, M.; Reinaud, O.; Rémita, S. Architecture-controlled "SMART"? calix[6]arene self-assemblies in aqueous solution Langmuir 2007, 23, 4849-4855 (Pubitemid 46731964)
10. Basí?lio, N.; Garcí?a-Rí?o, L.; Martií?n- Pastor, M. NMR evidence of slow monomer-micelle exchange in a calixarene-based surfactant J. Phys. Chem. B 2010, 114, 4816-4820
11. Basí?lio, N.; Garcí?a-Rí?o, L.; Martí?n- Pastor, M. Calixarene-based surfactants: Evidence of structural reorganization upon micellization Langmuir 2012, 28, 2404-2414
12. Helttunena, K.; Shahgaldian, P. Self-assembly of amphiphilic calixarenes and resorcinarenes in water New J. Chem. 2010, 34, 2704-2714
13. Zhang, X.; Wang, C. Supramolecular amphiphiles Chem. Soc. Rev. 2011, 40, 94-101
14. Basí?lio, N.; Garcí?a-Rí?o, L. Sulfonated calix[6]arene host-guest complexes induce surfactant self-assembly Chem.-Eur. J. 2009, 15, 9315-9319
15. Francisco, V.; Basí?lio, N.; Garcia-Rio, L.; Leis, J. R.; Marques, E. F.; Vázquez-Vázquez, C. Novel catanionic vesicles from calixarene and single-chain surfactant Chem. Commun. 2010, 46, 6551-6553
16. Wang, K.; Guo, D.-S.; Liu, Y. Temperature-controlled supramolecular vesicles modulated by p-sulfonatocalix[5]arene with pyrene Chem.-Eur. J. 2010, 16, 8006-8011
17. Wang, K.; Guo, D.-S.; Wang, X.; Liu, Y. Multistimuli responsive supramolecular vesicles based on the recognition of p-sulfonatocalixarene and its controllable release of doxorubicin ACS Nano 2011, 5, 2880-2894
18. Mayer, M.; Meyer, B. Characterization of ligand binding by saturation transfer difference NMR spectroscopy Angew. Chem., Int. Ed. 1999, 38, 1784-1788 (Pubitemid 29290947)
19. Meyer, B.; Peters, T. NMR spectroscopy techniques for screening and identifying ligand binding to protein receptors Angew. Chem., Int. Ed. 2003, 42, 864-890 (Pubitemid 36314024)
20. Neuhaus, D.; Williamson, M. The Nuclear Overhauser Effect in Structural and Conformational Analysis; VCH: New York, 2000.
21. Hu, H.; Krishnamurthy, K. Revisiting the initial rate approximation in kinetic NOE measurements J. Magn. Reson. 2006, 182, 173-177 (Pubitemid 44293442)
22. Yan, J.; Kline, A. D.; Mo, H.; Shapiro, M. J.; Zartler, E. R. The effect of relaxation on the epitope mapping by saturation transfer difference NMR J. Magn. Reson. 2003, 163, 270-276
23. Mayer, M.; James, T. L. NMR-based characterization of phenothiazines as a RNA binding scaffold J. Am. Chem. Soc. 2004, 126, 4453-4460 (Pubitemid 38453903)
24. Fritzinger, B.; Moreels, I.; Lommens, P.; Koole, R.; Hens, Z.; Martins, J. C. In situ observation of rapid ligand exchange in colloidal nanocrystal suspensions using transfer NOE nuclear magnetic resonance spectroscopy J. Am. Chem. Soc. 2009, 131, 3024-3032
25. Castro, R.; Godinez, L. A.; Crissm, C. M.; Bott, S. G.; Kaifer, A. E. Solid-state and solution complexation of cobalt(iii) sepulchrate by a water-soluble calix[6]arene host Chem. Commun. 1997, 935-936 (Pubitemid 127696172)
26. Alvarez, J.; Wang, Y.; Gó?mez-Kaifer, M.; Kaifer, A. E. Importance of intramolecular hydrogen bonding for preorganization and binding of molecular guests by water-soluble calix[6]arene hosts Chem. Commun. 1998, 1455-1456 (Pubitemid 128675643)
27. Castro, R.; Godí?nez, L. A.; Criss, C. M.; Kaifer, A. E. Host properties of α-cyclodextrin and a water-soluble calix[6]arene probed with dimeric bipyridinium guests J. Org. Chem. 1997, 62, 4928-4935
28. Casnati, A.; Jacopozzi, P.; Pochini, A.; Ugozzoli, F.; Cacciapaglia, R.; Mandolini, L.; Ungaro, R. Bridged calix[6]arenes in the cone conformation: New receptors for quaternary ammonium cations Tetrahedron 1995, 51, 591-598
29. Shinkai, S.; Araki, K.; Matsuda, T.; Nishiyama, N.; Ikeda, H.; Takasu, L.; Iwamoto, M. NMR and crystallographic studies of a p-sulfonatocalix[4]arene- guest complex J. Am. Chem. Soc. 1990, 112, 9053-9058
30. Arena, G.; Casnati, A.; Contino, A.; Lombardo, G. G.; Sciotto, D.; Ungaro, R. Water-soluble calixarene hosts that specifically recognize the trimethylammonium group or the benzene ring of aromatic ammonium cations: A combined 1H NMR, Ccalorimetric, and molecular mechanics investigation Chem.-Eur. J. 1999, 5, 738-744 (Pubitemid 129504180)
31. Arena, G.; Gentile, S.; Gulino, F. G.; Sciotto, D.; Sgarlata, C. Water-soluble pentasulfonatocalix[5]arene: selective recognition of ditopic trimethylammonium cations by a triple non-covalent interaction Tetrahedron Lett. 2004, 45, 7091-7094 (Pubitemid 39178571)
32. Guo, D.-S.; Wang, L.-H.; Liu, Y. Highly effective binding of methyl viologen dication and its radical cation by p-sulfonatocalix[4,5]arenes J. Org. Chem. 2007, 72, 7775-7778 (Pubitemid 47501650)
33. Beshara, C. S.; Jones, C. E.; Daze, K. D.; Lilgert, B. J.; Hof, F. A simple calixarene recognizes post-translationally methylated lysine ChemBioChem 2010, 11, 63-66
34. Bakirci, H.; Koner, A. L.; Nau, W. M. Spherical shape complementarity as an overriding motif in the molecular recognition of noncharged organic guests by p-sulfonatocalix[4]arene: Complexation of bicyclic azoalkanes J. Org. Chem. 2005, 70, 9960-9966 (Pubitemid 41689161)
35. Guo, D.-G.; Wang, K.; Liu, Y. Selective binding behaviors of p-sulfonatocalixarenes in aqueous solution J. Inclusion Phenom. Macrocyclic Chem. 2008, 62, 1-21
36. -1 in the bibliography, but care should be taken when comparisons are made, because some of them were obtained in the presence of an appreciable concentration of buffer, and sodium cations are known to compete with the guest for the complexation with SC n, resulting in observed binding constant significantly lower than that measured in the absence of added cations in solution. For detailed information, please see: Bakirci, H.; Koner, A. L.; Nau, W. M. Binding of inorganic cations by p-sulfonatocalix[4]arene monitored through competitive fluorophore displacement in aqueous solution Chem. Commun. 2005, 5411-5413 (Pubitemid 41689373)
37. Cui, J.; Uzunova, V. D.; Guo, D.-S.; Wang, K.; Nau, W. M.; Liu, Y. Effect of lower-rim alkylation of p-sulfonatocalix[4]arene on the thermodynamics of host-guest complexation Eur. J. Org. Chem. 2010, 1704-1710
38. Angulo, J.; Dí?az, I.; Reina, J. J.; Tabarani, G.; Fieschi, F.; Rojo, J.; Nieto, P. M. Saturation transfer difference (STD) NMR spectroscopy characterization of dual binding mode of a mannose disaccharide to DC-SIGN ChemBioChem 2008, 9, 2225-2227