Synthesis and self-assembly of thio derivatives of calix[4]arene on noble metal surfaces

Langmuir

Volumn 24, Issue 20, 2008, Pages 11523-11532

  Genorio, Boštjan ^a,b   He, Tao ^a   Meden, Anton ^c   Polanc, Slovenko ^c   Jamnik, Janko ^b   Tour, James M ^a  

^a RICE UNIVERSITY   (United States)

^b NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^c UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

ANCHORING GROUPS; CALCULATED VALUES; CALIX[4]ARENE; CALIX[4]ARENES; CAVITY DIMENSIONS; CONE CONFORMATIONS; CORE LEVELS; ELECTRODE SURFACES; FUEL CELL APPLICATIONS; LOW CONCENTRATIONS; METAL SURFACES; MONOMOLECULAR LAYERS; NOBLE METALS; ORGANIC MOLECULES; SELF-ASSEMBLY; SINGLE CRYSTAL X-RAY DIFFRACTIONS; SURFACE CHARACTERIZATIONS; TETRAKIS; X-RAY PHOTOELECTRON SPECTROSCOPIES;

AROMATIC COMPOUNDS; BINDING ENERGY; CONCENTRATION (PROCESS); CONFORMATIONS; CYCLIC VOLTAMMETRY; ELECTRIC BATTERIES; ELECTRON TRANSITIONS; ELLIPSOMETRY; FUEL CELLS; METALS; MISSILE BASES; MOLECULAR SIEVES; MOLECULAR SPECTROSCOPY; MOLECULES; MONOLAYERS; PALLADIUM; PASSIVATION; PHOTOELECTRON SPECTROSCOPY; PLATINUM; PLATINUM METALS; PRECIOUS METALS; SELF ASSEMBLED MONOLAYERS; SEMICONDUCTING SILICON COMPOUNDS; SIEVES; SILICON; SILICON WAFERS; SINGLE CRYSTALS;

X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 55549134646     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la802197u     Document Type: Article

References (84)

1. Encyclopedia of Electrochemistry: Modified Electrodes; Bard, A. J., Stratmann, M., Fujihira, M., Rubinstein, I., Rusling, J. F., Eds.; Wiley-VCH Verlag GmbH and Co. KGaA: Weinheim, Germany, 2007.
2. (a) Belanger, S.; Hupp, J. T. Angew. Chem., Int. Ed. 1999, 38, 2222-2224.
3. (b) Belanger, S.; Stevenson, K. J.; Mudakha, S. A.; Hupp, J. T. Langmuir 1999, 15, 837-343.
4. (c) Belanger, S.; Hupp, J. T.; Stern, C. L.; Slone, R. V.; Watson, D. F.; Carrell, T. G. J. Am. Chem. Soc. 1999, 121, 557-563.
5. (a) Ohsaka, T.; Hirokawa, T.; Miyamoto, H.; Oyama, N. Anal. Chem. 1987, 59, 1758-1761.
6. (b) Pontie, M.; Gobin, C.; Pauporte, T.; Bedioui, F.; Devynck, J. Anal. Chim. Acta 2000, 411, 175-185.
7. (a) Kornic, S.; Baker, M. Chem. Commun. 2002, 1700-1701.
8. (b) Zhang, Y.; Chen, F.; Shan, W.; Zhuang, J.; Dong, A.; Cai, W.; Tang, Y. Microporous Mesoporous Mater. 2003, 65, 277-285.
9. (c) Li, S.; Wang, X.; Beving, D.; Chen, Z.; Yan, Y. J. Am. Chem. Soc. 2004, 126, 4122-4123.
10. (d) Walcarius, A.; Ganesan, V.; Larlus, O.; Valtchev, V. Electroanalysis 2004, 16, 1550-1554.
11. (a) Markowitz, M. A.; Janout, V.; Castner, D. G.; Regen, S. L. J. Am. Chem. Soc. 1989, 111, 8192-8200.
12. (b) Dedek, P.; Janout, V.; Refen, S. L. J. Org. Chem. 1993, 58, 6553-6555.
13. (c) Zhang, L.; Hendel, R. A.; Cozzi, P. G.; Regen, S. L. J. Am. Chem. Soc. 1999, 121, 1621-1622.
14. (d) Yan, X.; Hsu, J. T.; Regen, S. L. J. Am. Chem. Soc. 2000, 122, 11944-11947.
15. (e) Yan, X.; Janout, V.; Hsu, J. T.; Regen, S. L. J. Am. Chem. Soc. 2002, 124, 10962-10963.
16. (f) Nakano, K.; Tanaka, S.; Takagi, M.; Shinkai, S. Chem. Lett. 2000, 60-61.
17. Ulman, A. An Introduction to Ultrathin Organic Films: From Langmuir-Blogett to Self-Assembly; Academic Press: San Diego, 1991.
18. Taniguchi, I.; Toyosawa, K.; Yamaguchi, H.; Yasukouchi, K. J. Chem. Soc., Chem. Commun. 1982, 1032-1033.
19. (a) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312-1319.
20. (b) Dubois, L. H.; Nuzzo, R. G. Annu. Rev. Phys. Chem. 1992, 43, 437-463.
21. (c) Ulman, A. Chem. Rev. 1996, 96, 153-1554.
22. (a) Laibinis, P. E.; Whitesides, G. M.; Allara, D. L.; Tao, Y. T.; Parikh, A. N.; Nuzzo, R. G. J. Am. Chem. Soc. 1991, 113, 7152-7167.
23. (b) Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Chem. Rev. 2005, 105, 1103-1169.
24. (c) Nuzzo, R. G.; Allara, D. L. J. Am. Chem. Soc. 1983, 105, 4481-4483.
25. Gutsche, C. D.; Muthukrishnan, R. J. Org. Chem. 1978, 43, 4905-4906.
26. (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
27. (b) Shinkai, S. Tetrahedron 1993, 49, 8933-8968.
28. (c) Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713-1734.
29. (d) Calixarenes in Action; Mandolini, L., Ungaro, R., Eds.; Imperial College Press: London, 2000.
30. (e) Calixarenes in the Nanoworld; Vicens, J., Harrowfield, J., Eds.; Springer: Dordrecht, Netherlands, 2007.
31. (f) Jose, P.; Menon, S. Bioinorg. Chem. Appl. 2007, 1-16.
32. (g) Rudkevich, D. M. Eur. J. Org. Chem. 2007, 3255-3270.
33. (a) Zhang, S.; Song, F.; Echegoyen, L. Eur. J. Org. Chem. 2004, 2936-1943.
34. (b) Evans, C. J.; Nicholson, G. P. Sens. Actuators B 2005, 105, 204-207.
35. Zhang, S.; Echegoyen, L. J. Org. Chem. 2005, 70, 9874-9881.
36. Cygan, M. T.; Collins, G. E.; Dunbar, T. D.; Allara, D. L.; Gibbs, C. G.; Gutsche, C. D. Anal. Chem. 1999, 71, 142-148.
37. Dalgarno, S. J.; Thallapally, P. K.; Brbour, L. J.; Atwood, J. L. Chem. Soc. Rev. 2007, 36, 236-245.
38. Estimated from CPK model, see also ref 11a, p 181.
39. Rojas, M. T.; Koniger, R.; Stoddart, J. F.; Kaifer, A. E. J. Am. Chem. Soc. 1995, 117, 336-343.
40. Beulen, M. W. J.; Kastenberg, M. I.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Langmuir 1998, 14, 7463-7467.
41. (a) Shirai, Y.; Cheng, L.; Chen, B.; Tour, J. M. J. Am. Chem. Soc. 2006, 128, 13479-13489.
42. (b) Yam, C. M.; Cho, J.; Cai, C. Langmuir 2003, 19, 6862-6868.
43. (c) Park, J-S.; Vo, A. N.; Barriet, D.; Shon, Y-S.; Lee, T. R Langmuir 2005, 21, 2902-2911.
44. Yasseri, A. A.; Syomin, D.; Malinovskii, V. L.; Loewe, R. S.; Lindsey, J. S.; Zaera, F.; Bocian, D. F. J. Am. Chem. Soc. 2004, 126, 11944-11953.
45. (a) Flink, S.; van Veggel, F. C. J. M.; Reinhoudt, D. N. Adv. Mater. 2000, 12, 1315-1327.
46. (b) James, D. K.; Tour, J. M. Anal. Chim. Acta 2006, 568, 2-19.
47. (a) Lane, R. F.; Hubbard, A. T. J. Phys. Chem. 1973, 77, 1401-1410.
48. (b) Lane, R. F.; Hubbard, A. T. J. Phys. Chem. 1973, 77, 1411-1421.
49. (c) Soriaga, M. P.; Hubbard, A. T. J. Am. Chem. Soc. 1982, 104, 3937-3945.
50. (d) Alvarez, J.; Liu, J.; Roman, E.; Kaifer, A. E. Chem. Commun. 2000, 1151-1152.
51. (e) Hickman, J. J.; Laibinis, P. E.; Auerbach, D. I.; Zou, C.; Gardner, T. J.; Whitesides, G. M.; Wrighton, M. S. Langmuir 1992, 8, 357-359.
52. (f) Li, Z.; Chang, S. C.; Williams, R. S. Langmuir 2003, 19, 6744-6749.
53. (g) Petrovykh, D. Y.; Kimura-Suda, H.; Opdahl, A.; Richter, L. J.; Tarlov, M. J.; Whitman, L. J. Langmuir 2006, 22, 2578-2587.
54. (a) Stewart, M. P.; Maya, F.; Kosynkin, D. V.; Dirk, S. M.; Stapleton, J. J.; McGuiness, C. L.; Allara, D. L.; Tour, J. M. J. Am. Chem. Soc. 2004, 126, 370-378.
55. (b) Love, J. C.; Wolfe, D. B.; Haasch, R.; Chabinyc, M. L.; Paul, K. E.; Whitesides, G. M.; Nuzzo, R. G. J. Am. Chem. Soc. 2003, 125, 2597-2609.
56. Vielstich, W.; Lamm, A.; Gasteiger, H. Handbook of Fuel Cells, Vol. 2, Electrocatalysis; Wiley: New York, 2003.
57. Aoki, H.; Buhlmann, P.; Umezawa, Y. J. Electroanal. Chem. 1999, 473, 105-112.
58. Hamada, F.; Bott, S. G.; Orr, G. W.; Coleman, A. W.; Zhang, H.; Atwood, J. L. J. Inclusion Phenom. Mol. Recognit. Chem. 1990, 9, 195-206.
59. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602-7605.
60. Field, L.; Grunwald, F. A. J. Org. Chem. 1951, 16, 946-953.
61. Batsanov, S. S. Inorg. Mater. 2001, 37, 871-885.
62. Balasubramanian, R.; Kwon, Y. G.; Wei, A. J. Mater. Chem. 2007, 17, 105-112.
63. James, D. K.; Tour, J. M. Aldrichim. Acta 2006, 59, 47-56.
64. Burilov, A. P.; Kharitonov, D. I.; Bashmakova, N. I.; Pudovik, M. A.; Konovalov, A. I. Russ. J. Gen. Chem. 2002, 72, 1144-1145.
65. van Hoorn, W. P.; Briels, W. J.; van Duynhoven, J. P. M.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Org. Chem. 1998, 68, 1299-1308.
66. In the case of 1b distance was calculated from the solved crystal structure and a linear Au-S-C bond with a 0.236 nm Au-S bond was assumed.
67. (a) Rieley, H.; Kendall, G. K.; Zemicael, F. W.; Smith, T. L.; Yang, S. Langmuir 1998, 14, 5147-5153.
68. (b) Lau, K. H. A.; Huang, C.; Yakovalev, N.; Chen, Z. K.; O'Shea, S. J. Langmuir 2006, 22, 2968-2971.
69. (a) Brito, R.; Rodriguez, V. A.; Figueroa, J.; Cabrera, C. R. J. Electroanal. Chem. 2002, 520, 47-52.
70. (b) Laiho, T.; Leiro, J. A.; Lukkari, J. Appl. Surf. Sci 2003, 212-213, 525-529.
71. Ron, H.; Matlis, S.; Rubinstein, I. Langmuir 1998, 14, 1116-1121.
72. Seah, M. P.; Smith, G. C. Smith; Anthony, M. T. Surf. Interface Anal. 1990, 15, 293-308.
73. Tressaud, A.; Khairoun, S.; Touhara, H.; Watanabe, N. Z Anorg. Allg. Chem. 1986, 540, 291-299.
74. Collect Software; Nonius, BV: Delft, The Netherlands, 1998.
75. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307.
76. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 52, 115.
77. Hall, S. R.; King, G. S. D.; Stewart, J. M. The Xtal3.4 User's Manual; University of Western Australia: Lamb, Perth 1995.
78. Wang, H.; Robertson, B. E. Structure and Statistics in Crystallography; Wilson, A. J. C., Ed.; Adenine Press, New York 1985.
79. Gutsche, C. D.; Lin, L. G. Tetrahedron 1986, 42, 1633-1640.
80. Gutsche, C. D.; Dhawan, B.; Levine, J. A.; No, K. H.; Bauer, L. J. Tetrahedron 1983, 39, 409-426.
81. Kenis, P. J. A.; Noordman, O. F. J.; Schonherr, H.; Kerver, E. G.; Snellink-Ruel, B. H. M.; van Hummel, G. J.; Harkema, S.; van der Vorst, C. P. J. M.; Hare, J.; Picken, S. J.; Engbersen, J. F. J.; van Hulst, N. F.; Vancso, G. J.; Reinoudt, D. N. Chem. Eur. J. 1998, 4, 1225-1234.
82. Gutsche, C. D.; Pagoria, P. F. J. Org. Chem. 1985, 50, 5795-5802.
83. Gu, T.; Ceroni, P.; Marconi, G.; Armaroli, N.; Nierengarten, J. F. J. Org. Chem. 2001, 66, 6432-6439.
84. Tour, J. M. Molecular Electronics: Commercial Insights, Chemistry, Devices, Architecture and Programming; World Scientific: Hackensack, NJ, 2003.