Effect of hydrogen bonding on the physicochemical properties and bilayer self-assembly formation of N-(2-hydroxydodecyl)-L-alanine in aqueous solution

Langmuir

Volumn 24, Issue 12, 2008, Pages 6018-6026

  Ghosh, Arjun ^a   Dey, Joykrishna ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; SELF ASSEMBLY; SOLUTIONS;

AGGREGATION BEHAVIORS; AQUEOUS SOLUTIONS; BI LAYERS; EFFECT OF HYDROGEN; L-ALANINE; PHYSICO-CHEMICAL PROPERTIES; SELF-ASSEMBLY;

HYDROGEN BONDS;

EID: 46949109016     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la800232x     Document Type: Article

References (101)

1. (a) Roy, S.; Dey, J. Langmuir 2003, 19, 9625-9629.
2. (b) Khatua, D.; Dey, J. J. Phys. Chem. B 2007, 111, 124-130.
3. Ohta, A.; Tani-I, K.; Hoshiba, A.; Asakawa, T.; Miyagishi, S. Chem. Lett. 2005, 34, 560-561.
4. Sakamoto, K.; Hatano, M. Bull. Chem. Soc. Jpn. 1980, 53, 339-343.
5. Shinitzky, M.; Haimovitz, R. J. Am. Chem. Soc. 1993, 115, 12545-12549.
6. (a) Du, X.; Hlady, V. J. Phys. Chem. B 2002, 106, 7295-7299.
7. (b) Bhattacharya, S.; Krishnan-Ghosh, Y. Chem. Commun. (Cambridge, U.K.) 2001, 185-186.
8. Luo, X.; Liu, B.; Liang, Y. Chem. Commun. (Cambridge, U.K.) 2001, 1556-1557.
9. Boetcher, C.; Schade, B.; Fuhrhop, J.-H. Langmuir 2001, 17, 873-877.
10. Imae, T.; Takahasshi, Y.; Muramatsu, H. J. Am. Chem. Soc. 1992, 114, 3414-3419.
11. Roy, S.; Khatua, D.; Dey, J. J. Colloid Interface Sci. 2005, 292, 255-264.
12. Pires, P. A. R.; El Seoud, O. A. Prog. Colloid Polym. Sci. 2006, 133, 131-141.
13. Shimizu, S.; Pires, P. A. R.; Fish, H. K.; Halstead, T. K.; El Seoud, O. A. Phys. Chem. Chem. Phys. 2003, 5, 3489-3497.
14. Shimizu, S.; Pires, P. A. R.; El Seoud, O. A. Langmuir 2003, 19, 9645-9652.
15. Shimizu, S.; El Seoud, O. A. Langmuir 2003, 19, 238-243.
16. (a) Du, X.; Liang, Y. J. Phys. Chem. B 2001, 105, 6092-6060.
17. (b) Du, X.; Liang, Y. J. Phys. Chem. B 2000, 104, 10047-10100.
18. Du, X.; Liang, Y. Langmuir 2000, 16, 3422-3434.
19. Du, X.; Hlady, V. J. Phys. Chem. B 2002, 106, 7295-7299, and references therein.
20. Roy, S.; Dey, J. Langmuir 2005, 21, 10362-10369.
21. Roy, S.; Dey, J. Bull. Chem. Soc. Jpn. 2006, 79, 59-66.
22. Roy, S.; Dey, J. J. Colloid Interface Sci. 2007, 307, 229-234.
23. Mohanty, A.; Dey, J. Langmuir 2004, 20, 8452-8459.
24. Mohanty, A.; Dey, J. Langmuir 2007, 23, 1033-1040.
25. Mohanty, A.; Patra, T.; Dey, J. J. Phys. Chem. B 2007, 111, 7155-7159.
26. Jeffy, G. A. An Introduction to Hydrogen Bonding; Oxford University Press: New York, 1997; pp 253-256.
27. MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420.
28. Kato, T.; Frechet, J. M. J. Macromolecules 1989, 22, 3818-3819.
29. Peleos, C. M.; Tsiourvas, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1696-1711.
30. Lange, R. F. M.; van Gurp, M.; Meijer, E. W. J. Polym. Sci., Part A: Polym. Chem. 1999, 37, 3657-3670.
31. (a) Bladon, P.; Griffin, A. C. Macromolecules 1993, 26, 6604-6410.
32. (b) Lutz, J.-F.; Pfeifer, S.; Chanana, M.; Thünemann, A. F.; Bienert, R. Langmuir 2006, 22, 7411-7415.
33. (a) Estoff, L. A.; Hamilton, A. D. Chem. Rev. 2004, 104, 1201-1217.
34. (b) Khatua, D.; Maity, R.; Dey, J. Chem. Commun. (Cambridge, U.K.) 2006, 4903-4905, and references therein.
35. Hidaka, H.; Murata, M.; Onai, T. Chem. Commun. (Cambridge, U.K.) 1984, 562-564.
36. Ueda, T.; Hidaka, H.; Harada, H.; Yamashita, Y.; Ohkura, A. Mol. Cryst. Liq. Cryst. 1982, 84, 231-243.
37. Siegel, S.; Vollhardt, D.; Cadenhead, D. A. Colloids Surf., A 2005, 256, 9-15, and references therein.
38. (a) Tachibana, T.; Yoshizumi, T.; Hori, K. Bull. Chem. Soc. Jpn. 1979, 52, 34-41.
39. (b) Tachibana, T.; Kambara, H. Bull. Chem. Soc. Jpn. 1969, 42, 3422-3424.
40. Zhang, L.; Lu, Q.; Liu, M. J. Phys. Chem. B 2003, 107, 2565-2569.
41. Yuan, J.; Liu, M. J. Am. Chem. Soc. 2003, 125, 5051-5056.
42. Blanzat, M.; Massip, S.; Spéziale, V.; Perez, E.; Rico-Lattes, I. Langmuir 2001, 17, 3512-3514.
43. Fuhrhop, J.-H.; Helfrich, W. Chem. Rev. 1993, 1565-1582.
44. Sylvain, V.; Santoso, S.; Gong, H.; Watson, N.; Zhang, S. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5355-5360.
45. Paramonov, S. E.; Jun, H. W.; Hartgerink, J. D. J. Am. Chem. Soc. 2006, 128, 7291-7298.
46. (a) Bong, D. T.; Clark, T. D.; Granja, J. R.; Ghadiri, M. R. Angew. Chem., Int. Ed. 2001, 40, 988-1011.
47. (b) Fernandez-Lopez, S.; Kim, H. S.; Choi, E. C.; Delgado, M.; Granja, J. R.; Khasanov, A.; Kraehenbuehl, K.; Long, G.; Weinberger, D. A.; Wilcoxen, K. M.; Gghadiri, M. R. Nature (London, U.K.) 2001, 41, 452-455.
48. Matsui, H.; Gologan, B. J. Phys. Chem. B 2000, 104, 3383-3386.
49. Matsui, H.; Douberly, G. E. Langmuir 2001, 17, 7918-7922.
50. Kogiso, M.; Ohnishi, S.; Yase, K.; Masuda, M.; Shimizu, T. Langmuir 1998, 14, 4978-4986.
51. Matsui, H.; Pan, S.; Gologan, B.; Jonas, S. J. Phys. Chem. B 2000, 104, 9576-9579.
52. Matsui, H.; Pan, S.; Douberly, G. E. J. Phys. Chem. B 2001, 105, 1683-1686.
53. Douberly, G. E.; Pan, S.; Walters, D.; Matsui, H. J. Phys. Chem. B 2001, 105, 7612-7618.
54. Matsui, H.; Gologan, B.; Pan, S.; Douberly, G. E. J. Eur. Phys. D 2001, 16, 403-406.
55. Matsui, H.; Porrata, P.; Douberly, G. E. Nano Lett. 2001, 461-464.
56. Ghosh, A.; Dey, J. J. Phys. Chem. B, submitted for publication.
57. Yoshimura, T.; Visihara, K.; Esumi, K. Langmuir 2005, 27, 10409-10415.
58. Pegiadou, S.; Perez, L.; Infante, M. R. J. Surfactants Deterg. 2000, 3, 517-524.
59. Ono, D.; Masuyama, A.; Nakatsuji, Y.; Okahara, M.; Yamamara, S.; Takeda, T. J. Am. Oil Chem. Soc. 1993, 70, 29-36.
60. Rosen, M. J. Surfactants and Interfacial Phenomena, 4th ed.; Wiley-Interscience: New York, 2004.
61. George, A.; Jain, N.; Desai, A.; Bahadur, P. Tenside Surfactants Deterg. 1998, 35, 368-374.
62. Varka, E. M.; Coutouli-Argyropoulou, E.; Infante, M. R.; Pegiadou, S. J. Surfactants Deterg. 2004, 7, 409-414.
63. Huang, J-B.; Mao, M.; Zhu, B-Y. Colloid Surf., A 1999, 155, 339-348.
64. (a) Félix, M.; Goñi, A. A. Biochim. Biophys. Acta 2000, 7508, 51-68.
65. (b) Saitoh, T.; Matsushima, S.; Hiraide, M. Colloids Surf., A 2007, 299, 88-92.
66. Nemkovich, N. A.; Baumann, W.; Kruchenok, Y. V.; Reis, H.; Rubinov, A. N. J. Fluoresc. 1997, 7, 363-370.
67. (a) Nayak, R. R.; Roy, S.; Dey, J. Colloid Polym. Sci. 2006, 285, 219-224.
68. (b) Roy, S.; Nayak, R. R.; Dey, J. Colloids Surf., A 2006, 290, 62-69.
69. An extensive compilation of spectral data of 1,8-ANS can be found in a review by Slavic et al. (Biochim. Biophys Acta 1982, 694, 1-25). Since the first excited (S 1) ICT state of the molecule is more stable in water, the gap between S 1 and T 1 states is reduced, thus enhancing the rate of intersystem crossing. Consequently, the molecule is weakly fluorescent in water at longer wavelengths. However, in nonpolar environments, the ICT state is destabilized, thus widening the gap between S 1 and T 1 states. As a result, the fluorescence intensity is enhanced, and the emission band shifts to shorter wavelengths.
70. (a) Bhattacharya, S.; Haldar, J. Langmuir 2004, 20, 7940-7947.
71. (b) Won, Y.-Y.; Brannan, A. K.; Davis, H. T.; Bates, F. S. J. Phys. Chem. B 2002, 106, 3354-3364.
72. Miyagishi, S.; Nishida, M. J. Colloid Interface Sci. 1978, 65, 380-386.
73. Kalyanasundaram, K.; Thomas, J. K. J. Am. Chem. Soc. 1977, 99, 2039-2044.
74. (a) Kalyansundaram, K. Photophysics of Microheterogeneous Systems; Academic Press: New York, 1988.
75. (b) Thomas, J. K. The Chemistry of Excitation at Interfaces: ACS Monograph 181; American Chemical Society: Washington, DC, 1984.
76. Winnik, F. M.; Regismond, S. T. A. Colloids Surf., A 1996, 118, 1-39.
77. Shinitzky, M.; Barenholz, Y. J. Biol. Chem. 1974, 249, 2652-2657.
78. Shinitzky, M.; Dianoux, A. C.; Itler, C.; Weber, G. Biochemistry 1971, 10, 2106-2113.
79. Shinitzky, M.; Yuli, I. Chem. Phys. Lipids 1982, 30, 261-282.
80. Debye, P. Polar Molecules; Dover: New York, 1929.
81. Roy, S.; Mohanty, A.; Dey, J. Chem. Phys. Lett. 2005. 414, 23-27.
82. Edward, J. T. J. Chem. Educ. 1970, 47, 261-270.
83. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Plenum Press: New York, 1983; p 132.
84. Shinitzky, M.; Barenholz, Y. J. Biol. Chem. 1974, 249, 2652-2657.
85. Singh, M.;Trivedi, M. K.; Bellare, J. J. Mater. Sci. 1999, 34, 5315-5323.
86. Hassan, P. A.; Raghavan, S. R.; Kaler, E. W. Langmuir 2002, 18, 2543-2548.
87. Bernheim-Groswasser, A.; Wachtel, E.; Talmon, Y. Langmuir 2000, 16, 4131-4140.
88. Gonzalez, Y. I.; Kaler, E. W. Curr. Opin. Colloid Interface Sci. 2005, 10, 256-260.
89. Shashkina, J. A.; Philoppova, O. E.; Zaroslov, Y. D.; Khokhlov, A. R.; Pryikhina, T. A.; Blagodatskikh, I. V. Langmuir 2005, 27, 1524-1530.
90. Flood, C.; Dreiss, C. A.; Croce, V.; Cosgrove, T.; Karlsson, G. Langmuir 2005, 27, 7646-7652.
91. Schubert, B. A.; Kaler, E. W.; Wagner, N. J. Langmuir 2003, 19, 4079-4089.
92. Raghavan, S. R.; Edlund, H.; Kaler, E. W. Langmuir 2002, 18, 1056-1064.
93. Bernheim-Groswasser, A.; Zana, R.; Talmon, Y. J. Phys. Chem. B 2000, 104, 4005-4009.
94. Bernheim-Groswasser, A.; Zana, R.; Talmon, Y. J. Phys. Chem. B 2000, 104, 12192-12201.
95. Koehler, R. D.; Raghavan, S. R.; Kaler, E. W. J. Phys. Chem. B 2000, 104, 11035-11044.
96. Kwon, S. Y.; Kim, M. W. Phys. Rev. Lett. 2002, 89, 258302-258304.
97. Porte, G.; Gomati, R.; El Haitami, O.; Appell, J.; Malignan, J. J. Phys. Chem. 1986, 90, 5746-5751.
98. Horbaschek, K.; Hoffmann, H.; Thunig, C. J. Colloid Interface Sci. 1998, 206, 439-456.
99. Shankar, B. V.; Patanaik, A. Langmuir 2007, 23, 3523-3529.
100. Israelachvili, J. N. Intermodular and Surface Forces, 2nd ed.; Academic Press: New York, 1991.
101. Yan, Y.;Xiong, W.; Li, X.; Lu, T.; Huang, J.; Li, Z.; Fu, H. J. Phys. Chem. B 2007, 111, 2225-2230.