Pyrogallol[4]arenes show highly variable amphiphilic behavior at the air-water interface dependent upon side chain length and branching

Chemistry - A European Journal

Volumn 17, Issue 32, 2011, Pages 8913-8921

  Daschbach, Megan M ^a   Kulikov, Oleg V ^a   Long, Elizabeth F ^a   Gokel, George W ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

amphiphiles; Brewster angle microscopy; Langmuir trough; pyrogallol 4 arenes; self assembly

Indexed keywords

AIR WATER INTERFACES; ALKYL CHAIN; ALKYL SIDE CHAINS; AMPHIPHILIC BEHAVIOR; AMPHIPHILIC SYSTEMS; AMPHIPHILICS; BRANCHED SIDE CHAINS; BREWSTER ANGLE MICROSCOPY; CALIXARENES; CARBON ATOMS; DIFFERENT MECHANISMS; LANGMUIR TROUGH; N-PROPYL; PYROGALLOL[4]ARENES; SIDE CHAIN LENGTHS; SIDE-CHAINS;

AIR; MONOLAYERS; PHENOLS;

PHASE INTERFACES;

CALIXARENE; DRUG DERIVATIVE; PYROGALLOL; PYROGALLOL(4)ARENE; SURFACTANT; WATER;

AIR; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STRUCTURE ACTIVITY RELATION; SURFACE PROPERTY;

AIR; CALIXARENES; MODELS, MOLECULAR; PYROGALLOL; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE PROPERTIES; SURFACE-ACTIVE AGENTS; WATER;

EID: 79960805576     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201100221     Document Type: Article

References (78)

1. C. D. Gutsche, Calixarenes, Vol. 1, RSC, Cambridge, 1989
2. Calixarenes: A Versatile Class of Macrocyclic Compounds (Topics in Inclusion Science) (Eds.:, J. Vicens, V. Böhmer,), Springer, Berlin, 1990, p. 280
3. Calixarenes in Action (Eds.:, L. Mandolini, R. Ungaro,), Imperial College Press, London, 2000, p. 271
4. C. D. Gutsche, Calixarenes Revisited, Vol. 6, RSC, Cambridge, 1998, p. 233
5. C. D. Gutsche, Calixarenes: An Introduction (Monographs in Supramolecular Chemistry), 2 nd ed., RSC, Cambridge, 2008; p. 248.
6. W. Sliwa, C. Kozlowski, Calixarenes and Resorcinarenes: Synthesis, Properties, and Applications, Wiley-VCH, Weinheim, 2009.
7. M. A. Markowitz, R. Bielski, S. L. Regen, J. Am. Chem. Soc. 1988, 110, 7545-7546.
8. R. A. Hendel, L.-H. Zhang, V. Janout, M. D. Conner, J. T. Hsu, S. L. Regen, Langmuir 1998, 14, 6545.
9. L.-H. E. Zhang, A. R. No, K. Yu, Langmuir 1999, 15, 1725-1730.
10. A. R. L.-H. Z. Esker, L.-H. Olsen, C. E. No, K. Yu, Langmuir 1999, 15, 1716-1724.
11. S. Jebors, F. Fache, S. Balme, F. Devoge, M. Monachino, S. Cecillon, A. W. Coleman, Org. Biomol. Chem. 2008, 6, 319-329
12. B. B. W. Ghera, A. Leydier, A. W. Coleman, J. Inclusion Phenom. Macrocyclic Chem. 2009, 64, 367-371
13. S. L. Jebors, O. Shkurenko, K. Kinga Suwinska, A. W. Coleman, J. Inclusion Phenom. Macrocyclic Chem. 2010, 68, 207-217.
14. L. Dei, P. C. LoNostro, P. Baglioni, Langmuir 1998, 14, 4143-4147.
15. G. de Miguel, J. M. Pedrosa, M. T. Martin-Romero, E. Munoz, T. H. Richardson, L. Camacho, J. Phys. Chem. B 2005, 109, 3998-4006.
16. A. R. Van der Heyden, P. Warszyriski, J.-O. Dalbavie, A. Zywocinski, E. Rogalska, Langmuir 2002, 18, 8854-8861.
17. J. C. Tyson, J. L. Moore, K. D. Hughes, D. M. Collard, Langmuir 1997, 13, 2068-2073.
18. M. K.-T. Strobel, A. Taubert, C. Vebert, P. A. Heiney, M. Chami, W. Meier, Adv. Funct. Mater. 2006, 16, 252-259.
19. D. Vollhardt, J. Gloede, G. Weidemann, R. Rudert, Langmuir 2003, 19, 4228-4234.
20. P. Shahgaldian, A. W. Coleman, S. S. Kuduva, M. J. Zaworotko, Chem. Commun. 2005, 1968-1970.
21. W. V. He, R. Rudert, L. Zhu, J. Li, Langmuir 2003, 19, 385-392.
22. W. C. D. Moreira, P. J. R. Aroca, Langmuir 1994, 10, 4148-4152
23. P. P. Prus, R. Bilewicz, Materials Sci. Eng.: C 2001, 18, 157-159.
24. Y. Ishikawa, T. Kunitake, T. Matsuda, T. Otsuka, S. Shinkai, J. Chem. Soc. Chem. Commun. 1989, 736-738.
25. D. Volkmer, M. Frieke, C. Agena, J. Mattay, CrystEngComm 2002, 4, 288-295
26. D. Volkmer, M. Frieke, C. Agena, J. Mattay, J. Mater. Chem. 2004, 14, 2249-2259.
27. M. Weis, R. Janicek, J. Cirak, T. Hianik, J. Phys. Chem. B 2007, 111, 10626-10631
28. P. Vitovic, D. P. Nikolelis, T. Hianik, Biochim. Biophys. Acta Biomembr. 2006, 1758, 1852-1861.
29. P. Shahgaldian, U. Pieles, M. Hegner, Langmuir 2005, 21, 6503-6507.
30. P. Shahgaldian, M. A. Sciotti, U. Pieles, Langmuir 2008, 24, 8522-8526.
31. N. B. Mel'nikova, E. Kh. Kazakova, I. V. Guljaev, A. A. Volkov, M. S. Gusikhina, L. Ya. Zakharova, M. A. Voronin, N. A. Markarova, L. A. Muslikina, A. I. Konovalov, Supramol. Chem. 2009, 21, 532-528.
32. M. W. R. Sugdena, F. Davis, S. P. J. Higson, C. F. J. Faul, Colloids Surf. A 2008, 321, 43-46.
33. P. Shahgaldian, M. Cesario, P. Goreloff, A. W. Coleman, Chem. Commun 2002, 326-327.
34. G. M. Merhi, M. Munoz, A. W. Coleman, G. Barrat, Supramol. Chem. 1995, 5, 173-177
35. L. Zhang, L. A. Godínez, T. Lu, G. W. Gokel, A. E. Kaifer, Angew. Chem. 1995, 107, 236-239
36. Angew. Chem. Int. Ed. Engl. 1995, 34, 235-237
37. O. R. Omar, A. K. Ray, A. K. Hassan F. Davis, Supramol. Sci. 1997, 4, 417-421
38. A. K. Hassan, A. V. Nabok, A. K. Ray, F. Davis, C. J. M. Stirling, Thin Solid Films 1998, 327, 686-689.
39. A. W. Coleman, S. Jebors, P. Shahgaldian, G. S. Ananchenko, J. A. Ripmeester, Chem. Commun. 2008, 2291-2303.
40. R. O. Çapan, H. Goktas, S. Sen, F. G. Ince, M. E. Ozel, G. A. Stanciu, F. Davis, Sens. Actuators B 2010, 148, 358-365.
41. T. Gerkensmeier, W. Iwanek, C. Agena, R. Fröhlich, S. Kotila, C. Näther, J. Mattay, Eur. J. Org. Chem. 1999, 2257-2262
42. T. Gerkensmeier, C. Agena, W. Iwanek, R. Fröhlich, S. Kotilad, C. Näther, J. Mattay, Z. Naturforsch. B 2001, 56, 1063-1073.
43. L. R. MacGillivray, J. L. Atwood, Nature 1997, 389, 469-472
44. J. Antesberger, G. W. V. Cave, M. C. Ferrarelli, M. W. Heaven, C. L. Raston, J. L. Atwood, Chem. Commun. 2005, 892-894
45. G. W. V. Cave, M. C. Ferrarelli, J. L. Atwood, Chem. Commun. 2005, 2787-2789
46. S. J. Dalgarno, G. W. Cave, J. L. Atwood, Angew. Chem. 2006, 118, 584-588
47. Angew. Chem. Int. Ed. 2006, 45, 570-4
48. S. J. Dalgarno, N. P. Power, J. L. Atwood, Coord. Chem. Rev. 2008, 252, 825-841
49. J. L. Atwood, L. J. Barbour, A. Jerga, Chem. Commun. 2001, 2376-2377.
50. A. Shivanyuk, J. C. Friese, S. Doring, J. Rebek, Jr. , J. Org. Chem. 2003, 68, 6489-6496
51. T. Evan-Salem, I. Baruch, L. Avram, Y. Cohen, L. C. Palmer, J. Rebek, Jr. , Proc. Nat. Acad. Sci. USA 2006, 103, 12296-12300.
52. G. W. Cave, J. Antesberger, L. J. Barbour, R. M. McKinlay, J. L. Atwood, Angew. Chem. 2004, 116, 5375-5378
53. Angew. Chem. Int. Ed. 2004, 43, 5263-5266.
54. S. J. Dalgarno, J. Antesberger, R. M. McKinlay, J. L. Atwood, Chem. Eur. J. 2007, 13, 8248-8255.
55. S. J. Dalgarno, N. P. Power, J. Antesberger, R. M. McKinlay, J. L. Atwood, Chem. Commun. 2006, 3803-3805.
56. O. V. Kulikov, M. M. Daschbach, C. R. Yamnitz, N. Rath, G. W. Gokel, Chem. Commun. 2009, 7497-7499.
57. A. Shivanyuk, E. F. Paulus, K. Rissanen, E. Kolehmainen, V. Bohmer, Chem. Eur. J. 2001, 7, 1944-51
58. H. Mansikkamäki, M. Nissinen, K. Rissanen, Angew. Chem. 2004, 116, 1263-1266
59. Angew. Chem. Int. Ed. 2004, 43, 1243-6
60. H. Mansikkamäki, S. Busi, M. Nissinen, A. Ahman, K. Rissanen, Chem. Eur. J. 2006, 12, 4289-96
61. K. Raatikainen, J. Huuskonen, M. Lahtinen, P. Metrangolo, K. Rissanen, Chem. Commun. 2009, 2160-2162.
62. Y. Tanaka, M. Miyachi, Y. Kobuke, Angew. Chem. 1999, 111, 565-567
63. Angew. Chem. Int. Ed. 1999, 38, 504-506
64. L. Avram, Y. Cohen, J. Am. Chem. Soc. 2003, 125, 16180-16181
65. L. Avram, Y. Cohen, J. Am. Chem. Soc. 2004, 126, 11556-11563
66. L. C. Palmer, J. Rebek Jr. , Org. Lett. 2005, 7, 787-789
67. S. J. Dalgarno, S. A. Tucker, D. B. Bassil, J. L. Atwood, Science 2005, 309, 2037-2039
68. D. B. Bassil, S. J. Dalgarno, G. W. Cave, J. L. Atwood, S. A. Tucker, J. Phys. Chem. B 2007, 111, 9088-9092.
69. R. Li, O. V. Kulikov, G. W. Gokel, Chem. Commun. 2009, 6092-6094.
70. E. E. Dueno, A. D. Hunter, M. Zeller, T. A. Ray, R. N. Salvatore, C. H. Zambrano, J. Chem. Crystallogr. 2007, 38, 181-187.
71. G. W. V. Cave, S. J. Dalgarno, J. Antesberger, M. C. Farrarelli, R. M. McKinlay, J. L. Atwood, Supramol. Chem. 2008, 20, 157-159.
72. R. M. McKinlay, P. K. Thallapally, G. W. Cave, J. L. Atwood, Angew. Chem. 2005, 117, 5879-5882
73. Angew. Chem. Int. Ed. 2005, 44, 5733-5736.
74. S. J. Dalgarno, N. P. Power, J. E. Warren, J. L. Atwood, Chem. Commun. 2008, 1539-1541.
75. B. Hille, Ionic Channels of Excitable Membranes, 3 rd ed., Sinauer, Sunderland, 2001, p. 814.
76. M. C. Petty, Langmuir-Blodgett Films: An Introduction, Cambridge University Press, Cambridge, 1996, p. 234.
77. Langmuir-Blodgett Films (Ed.:, G. G. Roberts,), Springer, New York, 1990, p. 444.
78. http://www.gimp.org/.