Synthesis and characterization of conjugated mono- and dithiol oligomers and characterization of their self-assembled monolayers

Langmuir

Volumn 19, Issue 10, 2003, Pages 4272-4284

  De Boer, Bert ^a   Meng, Hong ^b   Perepichka, Dmitrii F ^b   Zheng, Jie ^c   Frank, Martin M ^d,e   Chabal, Yves J ^d,e   Bao, Zhenan ^a  

^a LUCENT TECHNOLOGIES   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c OHIO UNIVERSITY   (United States)

^d RUTGERS UNIVERSITY   (United States)

^e AGERE SYSTEMS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CONTACT ANGLE; CYCLIC VOLTAMMETRY; ELLIPSOMETRY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MOLECULAR ORIENTATION; MOLECULAR STRUCTURE; MONOLAYERS; OPTICAL PROPERTIES; SELF ASSEMBLY; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY;

AROMATIC DITHIOLS; DITHIOL OLIGOMERS; GRAZING INCIDENCE; MOLECULAR ARRAYS;

OLIGOMERS;

EID: 0038784325     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la0341052     Document Type: Article

References (106)

1. Aviram, A.; Ratner, M. A. Chem. Phys. Lett. 1974, 29, 277.
2. Goldhaber-Gordon, D.; Montemerlo, M. S.; Love, J. C.; Opiteck, G. J.; Ellenbogen J. C. Proc. IEEE 1997, 85, 521.
3. Joachim, C.; Gimzewski, J. K.; Aviram, A. Nature 2000, 408, 541.
4. (a) Tans, S. J.; Verschueren, A. R. M.; Dekker, C. Nature 1998, 393, 49.
5. (b) Postma, H. W. Ch.; Teepen, T.; Yao, Z.; Grifoni, M.; Dekker, C. Science 2001, 293, 76.
6. (c) Derycke, V.; Martel, R.; Appenzeller, J.; Avouris, Ph. Nano Lett. 2001, 1, 453.
7. (d) Bachtold, A.; Hadley, P.; Nakanishi, T.; Dekker, C. Science 2001, 294, 1317.
8. Martel, R.; Schmidt, T.; Shea, H. R.; Hertel, T.; Avouris, Ph. Appl. Phys. Lett. 1998, 73, 2447.
9. Collier, C. P.; Mattersteig, G.; Wong, E. W.; Luo, Y.; Beverly, K.; Sampaio, J.; Raymo, F. M.; Stoddart, J. F.; Heath, J. R. Science 2000, 289, 1172.
10. Collier, C. P.; Wong, E. W.; Belohradský, M.; Raymo, F. M.; Stoddart, J. F.; Kuekes, P. J.; Williams, R. S.; Heath, J. R. Science 1999, 285, 391.
11. Cui, Y.; Wei, Q.; Park, H.; Lieber, C. M. Science 2001, 293, 1289.
12. Characterization of Organic Thin Films; Ulman, A., Ed.; Butterworth-Heinemann: Boston, 1995.
13. Ulman, A. Chem. Rev. 1996, 96, 1533.
14. Reed, M. A. MRS Bull. 2001, 26 (2), 113.
15. Seminario, J. M.; Zacarias, A. G.; Tour, J. M. J. Am. Chem. Soc. 1998, 120, 3970.
16. Tour, J. M. Chem. Rev. 1996, 96, 537.
17. Borman, S. Chem. Eng. News 2001, 79 (Dec. 10), 45.
18. Reed, M. A.; Zhou, C.; Muller, C. J.; Burgin, T. P.; Tour, J. M. Science 1997, 278, 252.
19. Fan, F. F.; Yang, J.; Dirk, S. M.; Price, D. W.; Kosynkin, D.; Tour, J. M.; Bard, A. J. J. Am. Chem. Soc. 2001, 123, 2454.
20. (a) Cui, X. D.; Primak, A.; Zarate, X.; Tomfohr, J.; Sankey, O. F.; Moore, A. L.; Moore, T. A.; Gust, D.; Harris, G.; Lindsay, S. M. Science 2001, 294, 571.
21. (b) Cui, X. D.; Primak, A.; Zarate, X.; Tomfohr, J.; Sankey, O. F.; Moore, A. L.; Moore, T. A.; Gust, D.; Nagahara, L. A.; Lindsay, S. M. J. Phys. Chem. B 2002, 106, 8609.
22. (a) Wold, D. J.; Frisbie, C. D. J. Am. Chem. Soc. 2000, 122, 2970.
23. (b) Wold, D. J.; Frisbie, D. C. J. Am. Chem. Soc. 2001, 123, 5549.
24. Vuillaume, D.; Boulas, C.; Collet, J.; Davidovits, J. V.; Rondelez, F. Appl. Phys. Lett. 1996, 69, 1646.
25. Boulas, C.; Davidovits, J. V.; Rondelez, F.; Vuillaume, D. Phys. Rev. Lett. 1996, 76, 4797.
26. Mayor, M.; von Hänisch, C.; Weber, H. B.; Reichert, J.; Beckmann, D. Angew. Chem., Int. Ed. 2002, 41, 1183.
27. Purcell, S. T.; Garcia, N.; Binh, V. T.; Jones, L., II; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11985.
28. Tour, J. M.; Jones, L., II; Pearson, D. L.; Lamba, J. J. S.; Burgin, T. P.; Whitesides, G. M.; Allara, D. L.; Parikh, A. N.; Atre, S. V. J. Am. Chem. Soc. 1995, 117, 9529.
29. Donhauser, Z. J.; Mantooth, B. A.; Kelly, K. F.; Bumm, L. A.; Monnell, J. D.; Stapleton, J. J.; Price, D. W., Jr.; Rawlett, A. M.; Allara, D. L.; Tour, J. M.; Weiss, P. S. Science 2001, 292, 2303.
30. Yaliraki, S. N.; Kemp, M.; Ratner, M. A. J. Am. Chem. Soc. 1999, 121, 3428.
31. Cygan, M. T.; Dunbar, T. D.; Arnold, J. J.; Bumm, L. A.; Shedlock, N. F.; Burgin, T. P.; Jones, L., II; Allara, D. L.; Tour, J. M.; Weiss, P. S. J. Am. Chem. Soc. 1998, 120, 2721.
32. Lin, P.-G.; Guyot-Sionnest, P. Langmuir 1999, 15, 6825.
33. Zehner, R. W.; Sita, L. R. Langmuir 1997, 13, 2973.
34. Reichert, J.; Ochs, R.; Beckmann, D.; Weber, H. B.; Mayor, M.; v. Löhneysen, H. Phys. Rev. Lett. 2002, 88, 176804-1.
35. Fendler, J. H. Chem. Mater. 2001, 13, 3196.
36. Nuzzo, R. G.; Allara, D. L. J. Am. Chem. Soc. 1983, 105, 4481.
37. Finklea, H. O. Electroanal. Chem. 1996, 19, 109.
38. Dunbar, T. D.; Cygan, M. T.; Bumm, L. A.; McCarty, G. S.; Burgin, T. P.; Reinerth, W. A.; Jones, L., II; Jackiw, J. J.; Tour, J. M.; Weiss, P. S.; Allara, D. L. J. Phys. Chem. B 2000, 104, 4880.
39. 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.
40. Walczak, M. M.; Chung, C.; Stole, S. M.; Widrig, C. A.; Porter, M. D. J. Am. Chem. Soc. 1991, 113, 2370.
41. (a) Twardowski, M.; Nuzzo, R. G. Langmuir 2002, 18, 5529.
42. (b) Kumar, A.; Abbott, N. L.; Biebuyck, H. A.; Kim, E.; Whitesides, G. M. Acc. Chem. Res. 1995, 28, 219.
43. Hong, S.; Reifenberger, R.; Tian, W.; Datta, S.; Henderson, J.; Kubiak, C. P. Superlattices Microstruct. 2000, 28, 289.
44. Dhirani, A.; Zehner, R. W.; Hsung, R. P.; Guyot-Sionnest, P.; Sita, L. R. J. Am. Chem. Soc. 1996, 118, 3319.
45. Dudek, S. P.; Sikes, H. D.; Chidsey, C. E. D. J. Am. Chem. Soc. 2001, 123, 8033.
46. Zhu, L.; Tang, H.; Harima, Y.; Yamashita, K.; Hirayama, D.; Aso, Y.; Otsubo, T. Chem. Commun. 2001, 1830.
47. Campbell, I. H.; Kress, J. D.; Martin, R. L.; Smith, D. L.; Barashkov, N. N.; Ferraris, J. P. Appl. Phys. Lett. 1997, 71, 3528.
48. Zehner, R. W.; Parsons, B. F.; Hsung, R. P.; Sita, L. R. Langmuir 1999, 15, 1121.
49. Hutchison, J. E.; Postlethwaite, T. A.; Murray, R. W. Langmuir 1993, 9, 3277.
50. (a) Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999, 286, 1550.
51. (b) Chen, J.; Wang, W.; Reed, M. A.; Rawlett, A. M.; Price, D. W.; Tour, J. M. Appl. Phys. Lett. 2000, 77, 1224.
52. Reed, M. A.; Chen, J.; Rawlett, A. M.; Price, D. W.; Tour, J. M. Appl. Phys. Lett. 2001, 78, 3735.
53. Metzger, R. M. Acc. Chem. Res. 1999, 32, 950.
54. Dhirani, A.; Lin, P.-H.; Guyot-Sionnest, P.; Zehner, R. W.; Sita, L. R. J. Chem. Phys. 1997, 106, 5249.
55. Park, J.; Pasupathy, A. N.; Goldsmith, J. I.; Chang, C.; Yaish, Y.; Petta, J. R.; Rinkoski, M.; Sethna, J. P.; Abruña, H. D.; McEuen, P. L.; Ralph, D. C. Nature 2002, 417, 722.
56. Liang, W.; Shores, M. P.; Bockrath, M.; Long, J. R.; Park, H. Nature 2002, 417, 725.
57. Hsung, R. P.; Babcock, J. R.; Chidsey, C. E. D.; Sita, L. R. Tetrahedron Lett. 1995, 36, 4525.
58. Sabatani, E.; Cohen-Boulakia, J.; Bruening, M.; Rubinstein, I. Langmuir 1993, 9, 2974.
59. Tour, J. M. Acc. Chem. Res. 2000, 33, 791.
60. Hicks, R. G.; Nodwell, M. B. J. Am. Chem. Soc. 2000, 122, 6746.
61. Suter, C. M. J. Am. Chem. Soc. 1931, 53, 1112.
62. Caesar, P. D. Org. Synth. Coll. Vol. IV 1963, 695.
63. Marvel, C. S.; Caesar, P. D. J. Am. Chem. Soc. 1951, 73, 1097.
64. Di Ventra, M.; Lang, N. D. Phys. Rev. B 2001, 65, 045402-1.
65. (a) Kobayashi, E.; Metaka, N.; Aoshima, S.; Furukawa, J. J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 227.
66. (b) Litvinenko, L. M.; Cheshko, R. S. J. Gen. Chem. USSR 1960, 30, 3682.
67. (c) Litvinenko, L. M.; Popova, R. S.; Popov, A. F. Russ. Chem. Rev. 1975, 44, 718.
68. (a) Houff, W. M.; Schuetz, R. D. J. Am. Chem. Soc. 1953, 75, 6316.
69. (b) Jones, E.; Moodie, I. M. Org. Synth. 1970, 50, 104.
70. (c) Adams, R.; Ferretti, A. J. Am. Chem. Soc. 1959, 81, 4939.
71. Rane, A. M.; Miranda, E. I.; Soderquist, J. A. Tetrahedron Lett. 1994, 35, 3225.
72. Jones, L., II; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388.
73. Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376.
74. Pinchart, A.; Dallaire, C.; Van Bierbeek, A.; Gingras, M. Tetrahedron Lett. 1999, 40, 5479.
75. Bumm, L. A.; Arnold, J. J.; Charles, L. F.; Dunbar, T. D.; Allara, D. L.; Weiss, P. S. J. Am. Chem. Soc. 1999, 121, 8017.
76. Handbook of Organic Conductive Molecules and Polymers; Nalwa, H. S., Ed.; John Wiley & Sons: New York, 1997; Vols 1-4.
77. Socci, E. P.; Farmer, B. L.; Baker, K. N. Polymer 1993, 34, 1571.
78. Kwan, W. S. V.; Atanasoska, L.; Miller, L. L. Langmuir 1991, 7, 1419.
79. Berlin, A.; Zotti, G. Macromol. Rapid Commun. 2000, 21, 301 and references therein.
80. (a) Fujihara, H.; Nakai, H.; Yoshihara, M.; Maeshima, T. Chem. Commun. 1999, 737.
81. (b) Liu, H.; Liu, S.; Echegoyen, L. Chem. Commun. 1999, 1493.
82. (c) Liu, S.; Liu, H.; Bandyopadhyay, K.; Gao, Z.; Echegoyen, L. J. Org. Chem. 2000, 65, 3292.
83. Exhaustive electrolysis (at the potential of the anodic peak) of 16 consumes four to six electrons per molecule (dependent on the electrolysis conditions), suggesting that not only the terthiophene core but also the side thiol groups are subject to oxidation. However, this value is not in direct connection with the kinetically controlled CV experiment, due to the irreversible nature of the process.
84. 2, calculating for the two-electron process.
85. Parikh, A. N.; Allara, D. L. J. Chem. Phys. 1992, 96, 927.
86. An isotropic refractive index is used to calculate the film thickness even though the refractive index is expected to be highly anisotropic for these SAMs, implying that the film thicknesses measured are relative thicknesses. Therefore, absolute tilt angles were not calculated from these data. The ellipsometric data support the formation of a single monolayer instead of multilayers. Recalculating the layer thicknesses with a (isotropic) refractive index of 1.45 gave rise to a ∼10% increase of the measured layer thickness.
87. (a) Liedberg, B.; Yang, Z.; Engquist, I.; Wirde, M.; Gelius, U.; Götz, G.; Bäuerle, P.; Rummel, R.-M.; Ziegler, Ch.; Göpel, W. J. Phys. Chem. B 1997, 101, 5951.
88. (b) Louarn, G.; Buisson, J. P.; Lefrant, S.; Fichou, D. J. Phys. Chem. 1995, 99, 11399.
89. Brower, T. L.; Garno, J. C.; Ulman, A.; Liu, G.-Y.; Yan, C.; Gölzhäuser, A.; Grunze, M. Langmuir 2002, 18, 6207.
90. Frey, S.; Stadler, V.; Heister, K.; Eck, W.; Zharnikov, M.; Grunze, M.; Zeysing, B.; Terfort, A. Langmuir 2001, 17, 2408.
91. (a) Fuxen, C.; Azzam, W.; Arnold, R.; Witte, G.; Terfort, A.; Wöll, C. Langmuir 2001, 17, 3689.
92. (b) Azzam, W.; Wehner, B. I.; Fisher, R. A.; Terfort, A.; Wöll, C. Langmuir 2002, 18, 7766.
93. Leung, T. Y. B.; Schwartz, P.; Scoles, G.; Schreiber, F.; Ulman, A. Surf. Sci. 2000, 458, 34.
94. Ishida, T.; Mizutani, W.; Azehara, H.; Sato, F.; Choi, N.; Akiba, U.; Fujihira, M.; Tokumoto, H. Langmuir 2001, 17, 7459.
95. Ishida, T.; Mizutani, W.; Choi, N.; Akiba, U.; Fujihara, M.; Tokumoto, H. J. Phys. Chem. B 2000, 104, 11680.
96. Chang, S.-C.; Chao, I.; Tao, Y.-T. J. Am. Chem. Soc. 1994, 116, 6792.
97. Tao, Y.-T.; Wu, C.-C.; Eu, J.-Y.; Lin, W.-L. Langmuir 1997, 13, 4018.
98. Ulman, A. Acc. Chem. Res. 2001, 34, 855.
99. (a) Chabal, Y. J. Phys. Rev. Lett. 1985, 55, 845.
100. (b) Reutt, J. E.; Chabal, Y. J.; Christman, S. B. Phys. Rev. B 1988, 38, 3112.
101. (a) Persson, B. N. J.; Volokitin, A. I. Surf. Sci. 1995, 310, 314.
102. (b) Volotkin, A. I.; Persson, B. N. J. Phys. Rev. B 1995, 52, 2899.
103. Henderson, J. I.; Feng, S.; Bein, T.; Kubiak, C. P. Langmuir 2000, 16, 6183.
104. Spectroscopic Ellipsometry and Reflectometry: A User's Guide; Tompkins, H. G., McGahan, W. A., Eds.; John Wiley & Sons: New York, 1999.
105. Ceasar, P. D. Org. Synth. Coll. IV 1963, 693.
106. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.