A supramolecular amphiphile from a new water-soluble calix[5]arene and n-dodecylammonium chloride

Tetrahedron Letters

Volumn 54, Issue 2, 2013, Pages 188-191

  Gattuso, Giuseppe ^a   Notti, Anna ^a   Pappalardo, Andrea ^b   Pappalardo, Sebastiano ^b   Parisi, Melchiorre F ^a   Puntoriero, Fausto ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

Calixarene; DOSY; Micelle; Sulfonato group; Supramolecular amphiphile

Indexed keywords

AMPHOPHILE; CALIX[5]ARENE; CALIXARENE; CHLORIDE; DODECYLAMMONIUM CHLORIDE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG; WATER;

ARTICLE; CRITICAL MICELLE CONCENTRATION; FLUORESCENCE SPECTROSCOPY; HYDRODYNAMICS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 84870404597     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.10.125     Document Type: Article

References (61)

1. L.L. Schramm, E.N. Stasiuk, and D.G. Marangoni Annu. Rep. Prog. Chem., Sect. C 99 2003 3 48
2. For some recent examples see: N. Basílio, and L. Garcia-Rio ChemPhysChem 13 2012 2368 2376
3. N.O. Mchedlov-Petrossyan, N.A. Vodolazkaya, R.V. Rodik, L.N. Bogdanova, T.A. Cheipesh, O.Yu. Soboleva, A.P. Kryshtal, L.V. Kutuzova, and V.I. Kalchenko J. Phys. Chem. C 116 2012 10245 10259
4. S. Fujii, Y. Sanada, T. Nishimura, I. Akiba, and K. Sakurai Langmuir 28 2012 3092 3101
5. V.V. Syakaev, E.Kh. Kazakova, J.E. Morozova, Y.V. Shalaeva, K.L. Shamil, and A.I. Konovalov J. Colloid Interface Sci. 370 2012 19 26
6. H. Huang, D.-M. Li, W. Wang, Y.-C. Chen, K. Khan, S. Song, and Y.-S. Zheng Org. Biomol. Chem. 10 2012 729 735
7. F. Perret, and A.W. Coleman Chem. Commun. 47 2011 7303 7319
8. A.D. Martin, and C.L. Raston Chem. Commun. 47 2011 9764 9772
9. Q. Liang, G. Chen, B. Guan, and M. Jiang J. Mater. Chem. 21 2011 13262 13267
10. G. Gattuso, G. Grasso, N. Marino, A. Notti, A. Pappalardo, S. Pappalardo, and M.F. Parisi Eur. J. Org. Chem. 2011 5696 5703
11. E.V. Ukhatskaya, S.V. Kurkov, S.E. Matthews, A. El Fagui, C. Amiel, F. Dalmas, and T. Loftsson Int. J. Pharm. 402 2010 10 19
12. K. Helttunen, and P. Shahgaldian New J. Chem. 34 2010 2704 2714
13. M. Rehm, M. Frank, and J. Schatz Tetrahedron Lett. 50 2009 93 96
14. M. Strobel, K. Kita-Tokarczyk, A. Taubert, C. Vebert, P.A. Heiney, M. Chami, and W. Meier Adv. Funct. Mater. 16 2006 252 259
15. N. Basílio, L. Garcia-Rio, and M. Martín-Pastor Langmuir 28 2012 2404 2414
16. D.-S. Guo, K. Wang, and Y. Liu J. Inclusion Phenom. Macrocyclic Chem. 62 2008 1 21
17. C. Gaeta, T. Caruso, M. Mincolelli, F. Troisi, E. Vasca, and P. Neri Tetrahedron 64 2008 5370 5378
18. J.L. Atwood, L.J. Barbour, M.J. Hardie, and C.L. Raston Coord. Chem. Rev. 222 2001 3 32
19. D.-S. Guo, K. Wang, Y.-X. Wang, and Y. Liu J. Am. Chem. Soc. 134 2012 10244 10250
20. K. Wang, D.-S. Guo, X. Wang, and Y. Liu ACS Nano 2011 2880 2894
21. K. Wang, D.-S. Guo, and Y. Liu Chem. Eur. J. 16 2010 8006 8011
22. S. Shinkai, H. Kawabata, T. Arimura, T. Matsuda, H. Satoh, and O. Manabe J. Chem. Soc., Perkin Trans. 1 1989 1073 1074
23. S. Shinkai, T. Arimura, K. Araki, H. Kawabata, H. Satoh, T. Tsubaki, O. Manabe, and J. Sunamoto J. Chem. Soc., Perkin Trans. 1 1989 2039 2045
24. Y. Tauran, A. Brioude, P. Shahgaldian, A. Cumbo, B. Kim, F. Perret, A.W. Coleman, and I. Montasserf Chem. Commun. 48 2012 9483 9485
25. S. Jebors, F. Fache, S. Balme, F. Devoge, M. Monachino, S. Cecillon, and A.W. Coleman Org. Biomol. Chem. 6 2008 319 329
26. C. Wang, Z. Wang, and X. Zhang Acc. Chem. Res. 45 2012 608 618
27. For references on calixarene-based supra-amphiphiles see: N. Basílio, M. Martín-Pastor, and L. Garcia-Rio Langmuir 28 2012 6561 6568
28. R.R. Kashapov, T.N. Pashirova, S.V. Kharlamov, A.Yu. Ziganshina, E.P. Ziltsova, S.S. Lukashenko, L.Ya. Zakharova, W.D. Habicher, S.K. Latypov, and A.I. Konovalov Phys. Chem. Chem. Phys. 13 2011 15891 15898
29. C. Tu, L. Zhu, P. Li, Y. Chen, Y. Su, D. Yan, X. Zhu, and G. Zhou Chem. Commun. 47 2011 6063 6065
30. V. Francisco, N. Basilio, L. Garcia-Rio, J.R. Leis, E.F. Marques, and C. Vázquez-Vázquez Chem. Commun. 46 2010 6551 6553
31. D.R. Stewart, M. Krawiec, R.P. Kashyap, W.H. Watson, and C.D. Gutsche J. Am. Chem. Soc. 117 1995 586 601
32. N. Basilio, L. Garcia-Rio, and M. Martín-Pastor J. Phys. Chem. B 114 2010 4816 4820
33. G.M.L. Consoli, G. Granata, R. Lo Nigro, G. Malandrino, and C. Geraci Langmuir 24 2008 6194 6200
34. F. Sansone, M. Dudic, G. Donofrio, C. Rivetti, L. Baldini, A. Casnati, S. Cellai, and R. Ungaro J. Am. Chem. Soc. 128 2006 14528 14536
35. Y. Cohen, L. Avram, and L. Frish Angew. Chem., Int. Ed. 44 2005 520 554
36. P.S. Denkova, L. Van Lokeren, I. Verbruggen, and R. Willem J. Phys. Chem. B 112 2008 10935 10941
37. K. Kalyanasundaram, and J.K. Thomas J. Am. Chem. Soc. 99 1977 2039 2044
38. N.J. Chang, and E.W. Kaler J. Phys. Chem. 89 1985 2996 3000
39. F. Arnaud-Neu, S. Fuangswasdi, A. Notti, S. Pappalardo, and M.F. Parisi Angew. Chem., Int. Ed. 37 1998 112 114
40. G. Ferguson, A. Notti, S. Pappalardo, M.F. Parisi, and A.L. Spek Tetrahedron Lett. 39 1998 1965 1968
41. S. Pappalardo, and M.F. Parisi J. Org. Chem. 61 1996 8724 8725
42. G. Gattuso, A. Notti, S. Pappalardo, M.F. Parisi, T. Pilati, and G. Terraneo CrystEngComm 14 2012 2621 2625
43. G. Gattuso, A. Notti, S. Pappalardo, M.F. Parisi, T. Pilati, G. Resnati, and G. Terraneo CrystEngComm. 11 2009 1204 1206
44. D. Garozzo, G. Gattuso, F.H. Kohnke, P. Malvagna, A. Notti, S. Occhipinti, S. Pappalardo, M.F. Parisi, and I. Pisagatti Tetrahedron Lett. 43 2002 7663 7667
45. A. Pappalardo, F.P. Ballistreri, G. Li Destri, P.G. Mineo, G.A. Tomaselli, R.M. Toscano, and G. Trusso Sfrazzetto Macromolecules 45 2012 7549 7556
46. V. Villari, G. Gattuso, A. Notti, A. Pappalardo, and N. Micali J. Phys. Chem. B 116 2012 5537 5541
47. A.K. Sharma, M. Caricato, E. Quartarone, S. Edizer, A. Giacometti Schieroni, R. Mendichi, and D. Pasini Polym. Bull. 69 2012 911 923
48. C. Capici, Y. Cohen, A. D'Urso, G. Gattuso, A. Notti, A. Pappalardo, S. Pappalardo, M.F. Parisi, R. Purrello, S. Slovak, and V. Villari Angew. Chem., Int. Ed. 50 2011 11956 11961
49. G. Gattuso, A. Notti, A. Pappalardo, M.F. Parisi, I. Pisagatti, S. Pappalardo, D. Garozzo, A. Messina, Y. Cohen, and S. Slovak J. Org. Chem. 73 2008 7280 7289
50. S. Pappalardo, V. Villari, S. Slovak, Y. Cohen, G. Gattuso, A. Notti, A. Pappalardo, I. Pisagatti, and M.F. Parisi Chem. Eur. J. 13 2007 8164 8173
51. C. Capici, R. De Zorzi, C. Gargiulli, G. Gattuso, S. Geremia, A. Notti, S. Pappalardo, M.F. Parisi, and F. Puntoriero Tetrahedron 66 2010 4987 4993
52. C. Gargiulli, G. Gattuso, C. Liotta, A. Notti, M.F. Parisi, I. Pisagatti, and S. Pappalardo J. Org. Chem. 74 2009 4350 4353
53. D. Garozzo, G. Gattuso, A. Notti, A. Pappalardo, S. Pappalardo, M.F. Parisi, M. Perez, and I. Pisagatti Angew. Chem., Int. Ed. 44 2005 4892 4896
54. D.A. Cristaldi, I. Fragalà, A. Pappalardo, R.M. Toscano, F.P. Ballistreri, G.A. Tomaselli, and A. Gulino J. Mater. Chem. 22 2012 675 683
55. F. Lupo, C. Capici, G. Gattuso, A. Notti, M.F. Parisi, A. Pappalardo, S. Pappalardo, and A. Gulino Chem. Mater. 22 2010 2829 2834
56. M. Giannetto, G. Mori, A. Notti, S. Pappalardo, and M.F. Parisi Anal. Chem. 70 1998 4631 4635
57. G.V. Oshovsky, D.N. Reinhoudt, and W. Verboom Angew. Chem., Int. Ed. 46 2007 2366 2393
58. O. Bistri, B. Colasson, and O. Reinaud Chem. Sci. 3 2012 811 818
59. S. Mahiuddin, O. Zech, S. Raith, D. Tourand, and W. Kunz Langmuir 25 2009 12516 12521
60. H. Chakraborty, and M. Sarkar Langmuir 20 2004 3551 3558
61. aq forcefield of the Spartan'10 suite (Wavefunction, Inc., Irvine, CA). See: Y. Shao, L.F. Molnar, Y. Jung, J. Kussmann, C. Ochsenfeld, S.T. Brown, A.T.B. Gilbert, L.V. Slipchenko, S.V. Levchenko, D.P. O'Neill, R.A. DiStasio Jr., R.C. Lochan, T. Wang, G.J.O. Beran, N.A. Besley, J.M. Herbert, C.Y. Lin, T. Van Voorhis, S.H. Chien, A. Sodt, R.P. Steele, V.A. Rassolov, P.E. Maslen, P.P. Korambath, R.D. Adamson, B. Austin, J. Baker, E.F.C. Byrd, H. Dachsel, R.J. Doerksen, A. Dreuw, B.D. Dunietz, A.D. Dutoi, T.R. Furlani, S.R. Gwaltney, A. Heyden, S. Hirata, C.-P. Hsu, G. Kedziora, R.Z. Khalliulin, P. Klunzinger, A.M. Lee, M.S. Lee, W.Z. Liang, I. Lotan, N. Nair, B. Peters, E.I. Proynov, P.A. Pieniazek, Y.M. Rhee, J. Ritchie, E. Rosta, C.D. Sherrill, A.C. Simmonett, J.E. Subotnik, H.L. Woodcock III, W. Zhang, A.T. Bell, A.K. Chakraborty, D.M. Chipman, F.J. Keil, A. Warshel, W.J. Hehre, H.F. Schaefer III, J. Kong, A.I. Krylov, P.M.W. Gilla, and M. Head-Gordon Phys. Chem. Chem. Phys. 8 2006 3172 3191