Current rectification through π-π Stacking in multilayered donor-acceptor cyclophanes

Journal of Physical Chemistry C

Volumn 116, Issue 50, 2012, Pages 26625-26635

  Tsuji, Yuta ^a   Yoshizawa, Kazunari ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

APPLIED BIAS; BONDED MOLECULE; COHERENT TRANSPORTS; CONJUGATED MOLECULES; CURRENT VOLTAGE CURVE; CYCLOPHANES; DECAY FACTOR; DONOR AND ACCEPTOR; DONOR-ACCEPTORS; ELECTRON TRANSPORT; ELECTRONIC DEVICE; FRONTIER ORBITAL ENERGIES; MOLECULAR LENGTH; MOLECULAR RECTIFIER; MULTI-LAYERED; NON EQUILIBRIUM GREEN'S FUNCTION METHOD; QUINONE ACCEPTORS; RECTIFICATION PROPERTIES; RECTIFICATION RATIO; RECTIFYING BEHAVIORS; STACKED MOLECULES; STACKED STRUCTURE; STACKING LAYERS; TRANSMISSION SPECTRUMS;

DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT PROPERTIES; PHENOLS; SEPARATION;

MOLECULES;

EID: 84871534862     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp308849t     Document Type: Article

References (94)

1. Carroll, R. L.; Gorman, C. B. Angew. Chem., Int. Ed. 2002, 41, 4378-4400
2. Tsutsui, M.; Taniguchi, M. Sensors 2012, 12, 7259-7298
3. Stokbro, K. J. Phys.: Condens. Matter 2008, 20, 064216
4. Lever, L. J.; Kelsall, R. W.; Bushby, R. J. Phys. Rev. B 2005, 72, 035130
5. Wu, J.; Pisula, W.; Müllen, K. Chem. Rev. 2007, 107, 718-747
6. Pisula, W.; Feng, X.; Müllen, K. Chem. Mater. 2011, 23, 554-567
7. Giese, B. Annu. Rev. Biochem. 2002, 71, 51-70
8. Endres, R. G.; Cox, D. L.; Singh, R. R. P. Rev. Mod. Phys. 2004, 76, 195-214
9. Genereux, J. C.; Barton, J. K. Chem. Rev. 2010, 110, 1642-1662
10. Xu, B. Q.; Tao, N. J. Science 2003, 301, 1221-1223
11. Kiguchi, M.; Murakoshi, K. Thin Solid Films 2009, 518, 466-469
12. Reed, M. A.; Zhou, C.; Muller, C. J.; Burgin, T. P.; Tour, J. M. Science 1997, 278, 252-254
13. Tsutsui, M.; Taniguchi, M.; Kawai, T. J. Am. Chem. Soc. 2009, 131, 10552-10556
14. Staykov, A.; Tsuji, Y.; Yoshizawa, K. J. Phys. Chem. C 2011, 115, 3481-3490
15. Li, X.; Staykov, A.; Yoshizawa, K. Bull. Chem. Soc. Jpn. 2012, 85, 181-188
16. Wu, S.; González, M. T.; Huber, R.; Grunder, S.; Mayor, M.; Schönenberger, C.; Calame, M. Nat. Nanotechnol. 2008, 3, 569-574
17. Martín, S.; Grace, I.; Bryce, M. R.; Wang, C.; Jitchati, R.; Batsanov, A. S.; Higgins, S. J.; Lambert, C. J.; Nichols, R. J. J. Am. Chem. Soc. 2010, 132, 9157-9164
18. Wang, L.-J.; Zhou, K.-G.; Tan, L.; Wang, H.; Shi, Z.-F.; Wu, G.-P.; Xu, Z.-G.; Cao, X.-P.; He, H.-X.; Zhang, H.-L. Chem.-Eur. J. 2011, 17, 8414-8423
19. Landauer, R. IBM J. Res. Dev. 1957, 1, 223-231
20. Datta, S. Quantum Transport: Atom to Transistor; Cambridge University Press: Cambridge, 2005.
21. Solomon, G. C.; Vura-Weis, J.; Herrmann, C.; Wasielewski, M. R.; Ratner, M. A. J. Phys. Chem. B 2010, 114, 14735-14744
22. Lin, L.-L.; Song, X.-N.; Luo, Y.; Wang, C.-K. J. Phys.: Condens. Matter 2010, 22, 325102
23. Zeng, J.; Chen, K.-Q.; He, J.; Zhang, X.-J.; Hu, W. P. Org. Electron. 2011, 12, 1606-1611
24. Franco, I.; Solomon, G. C.; Schatz, G. C.; Ratner, M. A. J. Am. Chem. Soc. 2011, 133, 15714-15720
25. Staykov, A.; Li, X.; Tsuji, Y.; Yoshizawa, K. J. Phys. Chem. C 2012, 116, 18451-18459
26. Lopinski, G. P.; Wayner, D. D. M.; Wolkow, R. A. Nature 2000, 406, 48-51
27. Piva, P. G.; DiLabio, G. A.; Pitters, J. L.; Zikovsky, J.; Rezeq, M.; Dogel, S.; Hofer, W. A.; Wolkow, R. A. Nature 2005, 435, 658-661
28. Smeu, M.; Wolkow, R. A.; Guo, H. J. Am. Chem. Soc. 2009, 131, 11019-11026
29. Dulić, D.; Tuukkanen, S.; Chung, C. L.; Isambert, A.; Lavie, P.; Filoramo, A. Nanotechnology 2009, 20, 115502
30. Liu, X.-Y.; Raynolds, J. E.; Wells, C.; Welch, J.; Cale, T. S. J. Appl. Phys. 2005, 98, 033712
31. Ohto, T.; Yamashita, K.; Nakamura, H. Phys. Rev. B 2011, 84, 045417
32. Jiang, J.; Smith, J. R.; Luo, Y.; Grennberg, H.; Ottosson, H. J. Phys. Chem. C 2011, 115, 785-790
33. Schneebeli, S. T.; Kamenetska, M.; Cheng, Z.; Skouta, R.; Friesner, R. A.; Venkataraman, L.; Breslow, R. J. Am. Chem. Soc. 2011, 133, 2136-2139
34. Breslow, R.; Schneebeli, S. T. Tetrahedron 2011, 67, 10171-10178
35. Kiguchi, M.; Takahashi, T.; Takahashi, Y.; Yamauchi, Y.; Murase, T.; Fujita, M.; Tada, T.; Watanabe, S. Angew. Chem., Int. Ed. 2011, 50, 5708-5711
36. Kiguchi, M.; Kaneko, S. ChemPhysChem 2012, 13, 1116-1126
37. Tsuji, Y.; Staykov, A.; Yoshizawa, K. J. Phys. Chem. C 2012, 116, 2575-2580
38. Tatemitsu, H.; Otsubo, T.; Sakata, Y.; Misumi, S. Tetrahedron Lett. 1975, 3059-3062
39. Machida, H.; Tatemitsu, H.; Sakata, Y.; Misumi, S. Tetrahedron Lett. 1978, 915-918
40. Machida, H.; Tatemitsu, H.; Otsubo, T.; Sakata, Y.; Misumi, S. Bull. Chem. Soc. Jpn. 1980, 53, 2943-2952
41. Staab, H. A.; Zapf, U.; Gurke, A. Angew. Chem., Int. Ed. Engl. 1977, 16, 801-803
42. Staab, H. A.; Schwendemann, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 756-757
43. Staab, H. A.; Zapf, U. Angew. Chem., Int. Ed. Engl. 1978, 17, 757-758
44. Schwartz, M. H. J. Inclusion Phenom. Mol. Recognit. Chem. 1990, 9, 1-35
45. Aviram, A.; Ratner, M. A. Chem. Phys. Lett. 1974, 29, 277-283
46. Ellenbogen, J. C.; Love, J. C. Proc. IEEE 2000, 88, 386-426
47. Stokbro, K.; Taylor, J.; Brandbyge, M. J. Am. Chem. Soc. 2003, 125, 3674-3675
48. Xue, Y.; Datta, S.; Ratner, M. A. J. Chem. Phys. 2001, 115, 4292-4299
49. Brandbyge, M.; Mozos, J.-L.; Ordejón, P.; Taylor, J.; Stokbro, K. Phys. Rev. B 2002, 65, 165401
50. Stokbro, K.; Taylor, J.; Brandbyge, M.; Mozos, J.-L.; Ordejón, P. Comput. Mater. Sci. 2003, 27, 151-160
51. In Molecular and Nano Electronics: Analysis, Design and Simulation; Seminario, J. M., Ed.; Elsevier: Amsterdam, 2006; Vol. 17.
52. Staykov, A.; Nozaki, D.; Yoshizawa, K. J. Phys. Chem. C 2007, 111, 11699-11705
53. Ford, M. J.; Hoft, R. C.; McDonagh, A. M.; Cortie, M. B. J. Phys.: Condens. Matter 2008, 20, 374106
54. Pan, J. B.; Zhang, Z. H.; Deng, X. Q.; Qiu, M.; Guo, C. Appl. Phys. Lett. 2011, 98, 013503
55. Liu, H.; Wang, N.; Li, P.; Yin, X.; Yu, C.; Gao, N.; Zhao, J. Phys. Chem. Chem. Phys. 2011, 13, 1301-1306
56. Nozaki, D.; Girard, Y.; Yoshizawa, K. J. Phys. Chem. C 2008, 112, 17408-17415
57. Choi, S. H.; Kim, B.; Frisbie, C. D. Science 2008, 320, 1482-1486
58. Nitzan, A.; Ratner, M. A. Science 2003, 300, 1384-1389
59. Fukazawa, A.; Kiguchi, M.; Tange, S.; Ichihashi, Y.; Zhao, Q.; Takahashi, T.; Konishi, T.; Murakoshi, K.; Tsuji, Y.; Staykov, A. Chem. Lett. 2011, 40, 174-176
60. Taniguchi, M.; Tsutsui, M.; Mogi, R.; Sugawara, T.; Tsuji, Y.; Yoshizawa, K.; Kawai, T. J. Am. Chem. Soc. 2011, 133, 11426-11429
61. Lörtscher, E. ChemPhysChem 2011, 12, 2887-2889
62. Tsuji., Y.; Staykov, A.; Yoshizawa, K. Thin Solid Films 2009, 518, 444-447
63. Tsuji., Y.; Staykov, A.; Yoshizawa, K. J. Phys. Chem. C 2009, 113, 21477-21483
64. Tsuji, Y.; Staykov, A.; Yoshizawa, K. J. Am. Chem. Soc. 2011, 133, 5955-5960
65. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006.
66. Rauk, A. Orbital Interaction Theory of Organic Chemistry; John Wiley & Sons: New York, 2001.
67. Díez-Pérez, I.; Hihath, J.; Lee, Y.; Yu, L.; Adamska, L.; Kozhushner, M. A.; Oleynik, I. I.; Tao, N. J. Nat. Chem. 2009, 1, 635-641
68. Nakamura, H.; Asai, Y.; Hihath, J.; Bruot, C.; Tao, N. J. J. Phys. Chem. C 2011, 115, 19931-19938
69. Frisch, M. J. Gaussian 09; revision A.01; Gaussian, Inc.: Wallingford, CT, 2009.
70. Perdew, J. P.; Burke, K.; Wang, Y. Phys. Rev. B 1996, 54, 16533-16539
71. Petersson, G. A.; Tensfeldt, T. G.; AL-Laham, M. A.; Shirley, W. A.; Mantzaris, J. J. Chem. Phys. 1988, 89, 2193-2218
72. Caramori, G. F.; Galembeck, S. E.; Laali, K. K. J. Org. Chem. 2005, 70, 3242-3250
73. Caramori, G. F.; Galembeck, S. E. J. Phys. Chem. A 2007, 111, 1705-1712
74. Yin, X.; Li, Y.; Zhang, Y.; Li, P.; Zhao, J. Chem. Phys. Lett. 2006, 422, 111-116
75. Li, Y.; Zhao, J.; Yin, X.; Yin, G. J. Phys. Chem. A 2006, 110, 11130-11135
76. ATK, version 11.8.1; QuantumWise, Copenhagen, Denmark, www.quantumwise.com.
77. Perdew, J. P.; Burke, K.; Ernzerhof, M. Phys. Rev. Lett. 1996, 77, 3865-3868
78. Ferrighi, L.; Madsen, G. K. H.; Hammer, B. J. Chem. Phys. 2011, 135, 084704
79. Toyoda, K.; Nakano, Y.; Hamada, I.; Lee, K.; Yanagisawa, S.; Morikawa, Y. Surf. Sci. 2009, 603, 2912-2922
80. Misumi, S.; Otsubo, T. Acc. Chem. Res. 1978, 11, 251-256
81. Cram, D. J.; Cram, J. M. Acc. Chem. Res. 1971, 4, 204-213
82. Mach, P.; Budzák, S.; Medveď, M.; Kysel, O. Theor. Chem. Acc. 2012, 131, 1-14
83. Stadler, R.; Geskin, V.; Cornil, J. J. Phys.: Condens. Matter 2008, 20, 374105
84. Salomon, A.; Cahen, D.; Lindsay, S.; Tomfohr, J.; Engelkes, V. B.; Frisbie, C. D. Adv. Mater. 2003, 15, 1881-1890
85. Tada, T.; Nozaki, D.; Kondo, M.; Hamayama, S.; Yoshizawa, K. J. Am. Chem. Soc. 2004, 126, 14182-12189
86. Tao, N. J. Nat. Nanotechnol. 2006, 1, 173-181
87. Yamada, R.; Kumazawa, H.; Noutoshi, T.; Tanaka, S.; Tada, H. Nano Lett. 2008, 8, 1237-1240
88. Liu, H.; Wang, N.; Zhao, J.; Guo, Y.; Yin, X.; Boey, F. Y. C.; Zhang, H. ChemPhysChem 2008, 9, 1416-1424
89. Karthäuser, S. J. Phys.: Condens. Matter 2011, 23, 013001
90. Liu, H.; Yu, C.; Gao, N.; Zhao, J. ChemPhysChem 2010, 11, 1895-1902
91. Elbing, M.; Ochs, R.; Koentopp, M.; Fischer, M.; von Hänisch, C.; Weigend, F.; Evers, F.; Weber, H. B.; Mayor, M. Proc. Natl. Acad. Sci. U. S. A 2005, 102, 8815-8820
92. Morales, G. M.; Jiang, P.; Yuan, S.; Lee, Y.; Sanchez, A.; You, W.; Yu, L. J. Am. Chem. Soc. 2005, 127, 10456-10457
93. Wang, W.; Yu, L. Langmuir 2011, 27, 2084-2087
94. Armstrong, N.; Hoft, R. C.; McDonagh, A.; Cortie, M. B.; Ford, M. J. Nano Lett. 2007, 7, 3018-3022