Self-assembly of a triangle-shaped, hexaplatinum-incorporated, supramolecular amphiphile in solution and at interfaces

Chemistry - A European Journal

Volumn 15, Issue 34, 2009, Pages 8566-8577

  Maran, Umamageswaran ^a   Britt, David ^b   Fox, Christopher B ^c   Harris, Joel M ^a,c   Orendt, Anita M ^a   Conley, Hiram ^d   Davis, Robert ^d   Hlady, Vladamir ^c   Stang, Peter J ^a  

^a UNIVERSITY OF UTAH   (United States)

^b UTAH STATE UNIVERSITY   (United States)

^c Department of Electrical and Computer Engineering   (United States)

^d BRIGHAM YOUNG UNIVERSITY   (United States)

Author keywords

Aggregates; Metallacycles; Self assembly; Supramolecular amphiphiles; Surface micelles

Indexed keywords

AFM IMAGE; AIR WATER INTERFACES; AMPHIPHILIC MACROCYCLE; AMPHIPHILICS; COACERVATE; FLAT TOPOLOGY; IN-SITU RAMAN SPECTROSCOPY; LIQUID-LIQUID INTERFACES; METALLACYCLES; MOLECULAR AREAS; MOLECULAR MODELS; MOLECULAR ORGANIZATION; MULTINUCLEAR NMR SPECTROSCOPY; PRECURSOR COMPOUNDS; SUPRAMOLECULAR AMPHIPHILES; SURFACE AGGREGATE; SURFACE MICELLES;

AGGLOMERATION; AGGREGATES; AMPHIPHILES; LIQUIDS; MICELLES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL MICROSCOPY; PLATINUM; RAMAN SPECTROSCOPY; SELF ASSEMBLY; SUPRAMOLECULAR CHEMISTRY;

PHASE INTERFACES;

3,6 DIBROMOPHENANTHRENE 9,10 QUINONE; 3,6-DIBROMOPHENANTHRENE-9,10-QUINONE; PHENANTHRENE DERIVATIVE; PLATINUM COMPLEX; QUINONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICELLE; NANOTECHNOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SURFACE PROPERTY;

MAGNETIC RESONANCE SPECTROSCOPY; MICELLES; MODELS, MOLECULAR; NANOTECHNOLOGY; ORGANOPLATINUM COMPOUNDS; PHENANTHRENES; QUINONES; SURFACE PROPERTIES;

EID: 69249128335     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200900595     Document Type: Article

References (88)

1. a) J.-M. Lehn, Supramolecular Chemistry Concepts and Perspectives, VCH, Weinheim, 1995, pp. 139-160;
2. b) M. Fujita, K. Umemoto, M. Yoshizawa, N. Fujita, T. Kusukawa, K. Biradha, Chem. Commun. 2001, 509-518;
3. c)B. Holliday, C. A. Mirkin, Angew. Chem. 2001, 113, 2076-2097;
4. Angew. Chem. Int. Ed. 2001, 40, 2022-2043;
5. d)D. L. Caulder, K. N. Raymond, Acc. Chem. Res. 1999, 32, 975-982;
6. e) S. Leininger, B. Olenyuk, P. J. Stang, Chem. Rev. 2000, 100, 853-908;
7. f) S. R. Seidel, P. J. Stang, Acc. Chem. Res. 2002, 35, 972-983.
8. a) B. Olenyuk, J. A. Whiteford, A. Fechtenkotter, P. J. Stang, Nature 1999, 398, 796-799;
9. b) D. L. Caulder, K. N. Raymond, J. Chem. Soc. Dalton Trans. 1999, 1185-1200;
10. c)S. Leininger, J. Fan, M. Schmitz, P. J. Stang, Proc. Natl. Acad. Sci. USA 2000, 97, 1380-1384;
11. d)M. Fujita, M. Tominaga, A. Hori, B. Therrien, Acc. Chem. Res. 2005, 38, 369-378;
12. e) Y. K. Kryschenko, S. R. Seidel, A. M. Arif, P. J. Stang, J. Am. Chem. Soc. 2003, 125, 5193-5198;
13. f) J. Stahl, W. Mohr, L. de Quadras, T. B. Peters, J. C. Bohling, J. M. Martin-Alvarez, G. R. Owen, F. Hampel, A. Gladysz, J. Am. Chem. Soc. 2007, 129, 8282-8295;
14. g) T. D. Hamilton, D. K. Bucar, L. R. MacGillivray, Chem. Commun. 2007, 16, 1603-1604;
15. h) L. R. MacGillivray, G. S. Papaefstathiou, T. Friscic, T. D. Hamilton, D. K. Bucar, Q. Chu, D. B. Varshney, I. G. Georgiev, Acc. Chem. Res. 2008, 41, 280-291.
16. a) N. Voyer, J. Roby, D. Deschênes, J. Bernier, Supramol. Chem. 1995, 5, 61-69;
17. b) Z. B. Huang, S. H. Chang, Synlett 2005, 2257-2259;
18. c)M. Sathiyendiran, R.-T. Liao, P. Thanasekaran, T.-T. Luo, N. S. Venkataramanan, G.-H. Lee, S.-M. Peng, K.-L. Lu, Inorg. Chem. 2006, 45, 10052-10054;
19. d)F. Huang, H.-B. Yang, N. Das, U. Maran, A. M. Arif, H. W. Gibson, P. J. Stang, J. Org. Chem. 2006, 71, 6623-6625;
20. e) K. Ghosh, H.-B. Yang, B. H. Northrop, M. M. Lyndon, Y.-R. Zheng, D. C. Muddiman, P. J. Stang, J. Am. Chem. Soc. 2008, 130, 5320-5334;
21. f) H. Jude, H. Disteldorf, S. Fischer, T. Wedge, A. M. Hawkridge, A. M. Arif, M. F. Hawthorne, D. C. Muddiman, P. J. Stang, J. Am. Chem. Soc. 2005, 127, 12131-12139;
22. g) H.-B. Yang, K. Ghosh, B. H. Northrop, Y.-R. Zheng, M. M. Lyndon, D. C. Muddiman, P. J. Stang, J. Am. Chem. Soc. 2007, 129, 14187-14189;
23. h) B. H. Northrop, H.-B. Yang, P. J. Stang, Chem. Commun. 2008, 45, 5896-5908;
24. i)N. C. Gianneschi, M. S. Masar, C. A. Mirkin, Acc. Chem. Res. 2005, 38, 825-837;
25. j) D. Fiedler, D. H. Leung, R. G. Bergman, K. N. Raymond, Acc. Chem. Res. 2005, 38, 349-358;
26. k) F. Würthner, C-C. You, C. R. Saha-Möller, Chem. Soc. Rev. 2004, 33, 133-146.
27. a) K. S. Birdi, Lipid and Biopolymer Monolayers at Liquid Interfaces, Plenum, New York, 1989, Section 4.7.1, pp. 87-91;
28. b) I. A. Aksay, M. Trau, S. Manne, I. Honma, N. Yao, L. Zhou, P. Fenter, P. M. Eisenberg, S. M. Gruner, Science 1996, 273, 892-898;
29. c)S. Manne, J. P. Cleveland, H. E. Gaub, G. D. Stucky, P. K. Hansma, Langmuir 1994, 10, 4409-4413;
30. d)M. Jaschke, H.-J. Butt, H. E. Gaub, S. Manne, Langmuir 1997, 13, 1381-1384;
31. e) E. J. Wanless, W. A. Ducker, J. Phys. Chem. 1996, 100, 3207-3214;
32. f) W. A. Ducker, E. J. Wanless, Langmuir 1996, 12, 5915-5920.
33. a) J. Zhu, A. Eisenberg, R. B. Lennox, J. Am. Chem. Soc. 1991, 113, 5583-5588;
34. b) L. F. Chi, M. Anders, H. Fuchs, R. R. Johnston, H. Ringsdorf, Science 1993, 259, 213-216;
35. c)T. Kato, M. Kameyama, M. Ehara, K.-i. Iimura, Langmuir 1998, 14, 1786-1798;
36. d)M. Maaloum, R Muller, M. R Krafft, Angew. Chem. 2002, 114, 4507-4510;
37. Angew. Chem. Int. Ed. 2002, 41, 4331-4334;
38. e) C. Qibin, L. Xiaodong, W. Shaolei, X. Shouhong, L. Honglai, H. Ying, J. Colloid Interface Sci. 2007, 314, 651-658.
39. a) B. Porta, J. Khamsi, J. C. Noveron, Curr. Org. Chem., 2008, 12, 1298-1321;
40. b) N. Kimizuka, N. Oda, T. Kunitake, Inorg. Chem. 2000, 39, 2684-2689;
41. c)B. W.-K. Chu, V. W-W Yam, Inorg. Chem. 2001, 40, 3324-3329.
42. a) M. Castriciano, A. Romeo, R. Romeo, L. Monsu 'Scolaro, Eur. J. Inorg. Chem. 2002, 531-534;
43. b) J. Bowers, K. E. Amos, D. W. Bruce, R. K. Heenan, Langmuir 2005, 21, 5696-5706;
44. c)J. Bowers, K. E. Amos, D. W. Bruce, J. R. R Webster, Langmuir 2005, 21, 1346-1353;
45. d)D. Dominguez-Gutierrez, M. Surtchev, E. Eiser, C. J. Elsevier, Nano Lett. 2006, 6, 145-147;
46. e) P. Thanasekaran, J.-Y. Wu, B. Mani- maran, T. Rajendran, I.-J. Chang, S. Rajagopal, G.-H. Lee, S.-M. Peng, K.-L. Lu, J. Phys. Chem. A 2007, 111, 10953-10960;
47. f) N. Sakai, S. Matile, Angew. Chem. 2008, 120, 2-2;
48. Angew. Chem. Int. Ed. 2008, 47, 2-7;
49. g) M. Jung, H. Kim, K. Baek, K. Kim, Angew. Chem. 2008, 120, 5839-5841;
50. Angew. Chem. Int. Ed. 2008, 47, 5755-5757;
51. h) P. C. Wilson, S. J. Webb, Chem. Commun. 2008, 4007-4009;
52. i)T. M. Fyles, C. C. Tong, New J. Chem. 2007, 31, 655-661;
53. j) B. H. Northrop, A. Glöckner, P. J. Stang, J. Org. Chem. 2008, 73, 1787-1794.
54. a) J. M. Fox, N. R. Goldberg, T. J. Katz, J. Org. Chem. 1998, 63, 7456-7462;
55. b) M. V. Bhatt, Tetrahedron 1964, 20, 803-821;
56. c)J. Schmidt, M. Eitel, J. Prakt. Chem. 1932, 134, 167-176;
57. d)T. Yoshi- da, T. Matsuda, S. Otsuka, G. W. Parshall, W. G. Peet, R Binger, A. Brinkmann, R Wedemann, Inorg. Synth. 2007, 19, 107-110.
58. a) K. Paruch, T. J. Katz, C. Incarvito, K.-C. Lam, B. Rhatigan, A. L. Rheingold, J. Org. Chem. 2000, 65, 7902-7908;
59. b) U. Maran, H. Conley, M. Frank, A. M. Arif, A. M. Orendt, D. Britt, V. Hlady, R. Davis, R J. Stang, Langmuir 2008, 24, 5400-5410;
60. c)M. Wang, K. M. Liechti, Q. Wang, J. M. White, Langmuir 2005, 21, 1848-1857.
61. R. Narayanan, M. A. El-Sayed, J. Am. Chem. Soc. 2004, 126, 7194-7195.
62. L. J. W. Shimon, M. Vaida, L. Addadi, M. Lahav, L. Leiserowitz, J. Am. Chem. Soc. 1990, 112, 6215-6220.
63. a) J. Vacek, D. C. Caskey, D. Horinek, R. K. Shoemaker, R J. Stang, J. Michl, J. Am. Chem. Soc. 2008, 130, 7629-7638;
64. b) D. C. Caskey, T. Yamamoto, C. Addicott, R. K. Shoemaker, J. Vacek, A. M. Hawk- ridge, D. C. Muddiman, G. S. Kottas, J. Michl, R J. Stang, J. Am. Chem. Soc. 2008, 130, 7620-7638;
65. c)C. J. Kuehl, S. D. Huang, P. J. Stang, J. Am. Chem. Soc. 2001, 123, 9634-9641, and references [20a-a] therein;
66. d)J. R. Hall, S. J. Loeb, G. K. H. Shimizu, G. R A. Yap, Angew. Chem. 1998, 110, 130-133;
67. Angew. Chem. Int. Ed. 1998, 37, 121-123.
68. a) Gaussian 03, Revision D.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, R Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Wallingford CT, 2004;
69. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652;
70. c)C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
71. d)P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 270-310.
72. a) F. M. Menger, A. V. Peresypkin, K. L. Caran, R. P. Apkarian, Langmuir 2000, 16, 9113-9116;
73. b) R. Zana, M. In in Gemini Surfactants: Synthesis Interfacial and Solution-Phase Behavior, and Applications, Surfactant Science Series, Vol.117 (Eds.: R. Zana, J. Xia), Marcel Dekker, New York, 2004, pp. 211-232.
74. a) M. E. Cates, P. S. Clegg, Soft Matter 2008, 4, 2132-2138, and references therein;
75. b) R S. Clegg, J. Phys. Condens. Matter 2008, 20, 1-18.
76. a) M. Suzuki, Y. Niidome, S. Yamada, Thin Solid Films 2006, 496, 140-141;
77. b) Benzene Product Information, FTIR Raman Spectrum, Sigma-Aldrich, 2008;
78. c)C. J. Orendorff, M. W. Ducey, J. E. Pemberton, J. Phys. Chem. A 2002, 106, 6991-6998;
79. d)C. B. Fox, R. H. Uibel, J. M. Harris, J. Phys. Chem. B 2007, 4, 11428-11436;
80. e) R. Faggiani, B. Lippert, C. J. L. Lock, Inorg. Chem. 1982, 21, 3210-3216.
81. a) H. Matsumura, K. Furusawa in Electrical Phenomena at Interfaces: Fundamentals: Measurements, and Applications, Surfactant Science Series, Vol.76, 2nd ed. (Eds.: H. Ohshima, K. Furusawa), Marcel Dekker, New York, 2004, Chapter 11, pp. 253-264;
82. b) R. Aveyard, D. A. Haydon, An Introduction to the Principles of Surface Chemistry, University Press, Cambridge, 1973, Chapter 2, pp. 31-57.
83. a) H. Grüniger, D. Möbius, H. Meyer, J. Chem. Phys. 1983, 79, 3701-3710;
84. b) D. Möbius in Langmuir-Blodgett Films (Ed.: G. Roberts), Plenum Press, New York, 1990, pp. 223-271.
85. S. May, A. Ben-Shaul in Giant Micelles, Surfactant Science Series, Vol.140 (Eds.: R. Zana, E. Kaier), CRC, Florida, 2007, Chapter2, pp. 41-79.
86. a) W. P. Ozimin'skia, R Gamuszeka, E. Bednareka, J. C. Dobrowolskia, Inorg. Chim. Acta 2007, 360, 1902-1914;
87. b) D. Karhánek, P. Kačer, M. Kuzma, J. Šplí chalová, L. Červený, J. Mol. Model. 2007, 13, 1009-1016.
88. D. R Cherney, J. C. Conboy, J. M. Harris, Anal. Chem. 2003, 75, 6621-6628.