Stable room-temperature molecular negative differential resistance based on molecule-electrode interface chemistry

Journal of the American Chemical Society

Volumn 126, Issue 37, 2004, Pages 11648-11657

  Salomon, Adi ^a   Arad Yellin, Rina ^a   Shanzer, Abraham ^a   Karton, Amir ^a   Cahen, David ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTRIC CURRENTS; ELECTRODES; FERMI LEVEL; MOLECULAR VIBRATIONS; MOLECULES; REDUCTION; SOLVENTS; SURFACE CHEMISTRY; SYSTEM STABILITY;

CYCLIC DISULFIDE; DIFFERENTIAL RESISTANCE; INSULATING BARRIER; MOLECULES ALIGNMENT;

MERCURY (METAL);

DISULFIDE; MERCURY;

ADSORPTION; ARTICLE; ELECTRIC POTENTIAL; ELECTROCHEMISTRY; ELECTRODE; ENERGY; MOLECULE; REDUCTION; ROOM TEMPERATURE; SOLID STATE;

EID: 4544373598     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049584l     Document Type: Article

References (79)

1. Cahen, D.; Modes, G. Adv. Mater. 2002, 11, 789-798.
2. Heath, J. R.; Ratner, M. A. Physics Today 2003, May, 43-49.
3. Hipps, K. W. Science 2001, 294, 535-537.
4. Stewart, D. R.; Ohlberg, D. A. A.; Beck, P. A.; Chen, Y.; Williams, S. R. Nano Lett. 2004, 4, 133-136.
5. Cui, X. D.; Primak, A.; Zarate, X.; Tomfohr, J.; Sankey, O. F.; Lindsay, S. M. Science 2001, 294, 571-574.
6. Selzer, Y.; Salomon, A.; Cahen, D. J. Phys. Chem. B 2002, 106, 10432-10439.
7. Salomon, A.; Cahen, D.; Lindsay, S.; Tomfohr, J.; Engelkes, V.; Frisbie, C. D. Adv. Mater. 2003, 15, 1881-1890.
8. Beebe, J. M.; Engelkes, V. B.; Miller, L. L.; Frisbie, C. D. J. Am. Chem. Soc. 2002, 124, 11268.
9. Kushmerick, J. G.; Holt, D. B.; Yang, J. C. Phys. Rev. Lett. 2002, 89, 086802-086801.
10. Tivanski, A. V.; He, Y.; Liu. H.; Walker, G. C.; Waldeck, D. H. submitted.
11. Tung, R. T. Phys. Rev. Lett. 2000, 84, 6078-6081.
12. Vilan, A.; Shanzer, A.; Cahen, D. Nature 2000, 404, 166-168.
13. Salomon, A.; Berkovich, D.; Cahen, D. Appl. Phys. Lett. 2003, 82, 1051-1053.
14. Wassel, R. A.; Credo, G. M.; Fuierer, R. R.; Feldheim, D. L.; Gorman, C. B. J. Am. Chem. Soc. 2004, 126, 295-300.
15. Karzazi, Y.; Cornil, J.; Bredas, J. L. Nanotechnology 2002, 13, 336.
16. Chen, J.; Reed, M. A.; Rawlett, A. M.; Tour, J. M. Science 1999, 286, 1550-1551.
17. Rakshit, T.; Liang, G. C.; Ghosh, W. A.; Datta, S. Phys. Rev. Lett. 2004, in press.
18. Guisinger, N. P.; Greene, M. E.; Basu, R.; Baluch, A. S.; Hersam, M. C. Nano Lett. 2004, 4, 55-59.
19. Gorman, C. B.; Carroll, R. L.; Fuierer, R. R. Langmuir 2001, 17, 6923-6930.
20. Zeng, C.; Wang, H.; Yang, J.; Hou, J. G. Appl. Phys. Lett. 2000, 77, 3595-3597.
21. Chen, J.; Wang, H.; Reed, M. A. Appl. Phys. Lett. 2000, 77, 1224-1226.
22. Kratochvilova, I.; Kocirik, M.; Zambova, A.; Mbindyo, J.; Mallouk, T. E; Mayer, T. S. J. Mater. Chem. 2002, 12, 2927-2930.
23. Fan, F. R. F.; Yang, J. P.; Cai, L. T.; Price, D. W.; Dirk, S. M.; Kosynkin, D. V.; Yao, Y. X.; Rawlett, A. M.; Tour, J. M.; Bard, A. J. J. Am. Chem. Soc. 2002, 124, 5550-5560.
24. Le, J. D.; He, J.; Hoye, T. R.; Mead, C. C.; Kiehl, R. A. Appl. Phys. Lett. 2003, 83, 5518-5520.
25. Selzer, Y.; Salomon, A.; Ghabboun, J.; Cahen, D. Angew. Chem., Int. Ed. 2002, 41, 827-830.
26. Lu, P.; Alterman, M. A.; Chaurasia, C. S.; Bambal, R. B.; Hanzlik, R. P. Arch. Biochem. Biophys. 1997,337, 1-7.
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, Jr. J. A.; Vreven, T.; Kudin, K. N. Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A. Makatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R. Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, Jr., S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liaskenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.02; Gaussian, Inc.: Pittsburgh, 2003.
28. Dunning, T. H. J.; Hay, P. J. In Modern Theoretical Chemistry, 3d ed.; Schaefer, H. F., Ed.; Plenum Press: New York, 1997; Vol. 4.
29. Dolg, M. In Modern Methods and Algorithms of Quantum Chemistry; Grotendort, J., Ed.; John von Neumann Institute for Computing: Julich, 2000; Vol. 1, pp 479-508.
30. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209.
31. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221.
32. 3) on Au (cf. Bruening et al.41), as we could not make such measurements for the molecules on Hg. Of special relevance were the ellipsometric thickness and the tilt angle of the alkyl chains relative to the surface normal.
33. The energies of the (free) molecules were calculated at the SAOP/TZZP level of theory and were found to be between 15 and 50 kJ/mol higher than those with the PM3 optimized geometry.
34. Israelachvili, J. Intermolecular & Surface Forces, 2nd ed.; Elsevier: London, 1991.
35. Fonseca Guerra, C.; Snijders, J. G.; te Velde, G.; Baerends, E. J. Theor. Chem. Acc. 1998, 99, 391.
36. Schipper, P. R. T.; Gritsenko, O. V.; van Gisbergen, S. J. A.; Baerends, E. J. J. Chem. Phys. 2000, 112, 1344.
37. te Velde, G.; Bickelhaupt, F. M.; van Gisbergen, S. J. A.; Fonseca Guerra, C.; Baerends, E. J.; Snijders, J. G.; Zigler, T. J. Comput. Chem. 2001, 22, 931-967.
38. Gruning, M.; Gritsenko, O. V.; Gisbergen, S. J. A. v.; Baerends, E. J. J. Chem. Phys. 2002, 116, 9591.
39. Dunning, T. J. J. Chem. Phys. 1989, 90, 1007-1023.
40. Kendall, R. A.; Dunning, T. J.; Harrison, R. J. J. Chem. Phys. 1992, 96, 6796.
41. Bruening, M.; Cohen, R.; Guillemoles, J. F.; Moav, T.; Libman, J.; Shanzer, A.; Cahen, D. J. Am. Chem. Soc. 1997, 119, 5720-5728.
42. Vilan, A.; Ghabboun, J.; Cahen, D. J. Phys. Chem. B 2003, 107, 6360-6376.
43. Haag, R.; Rampi, M. A.; Holmlin, R. E.; Whitesides, G. M. J. Am. Chem. Soc. 1999, 121, 7895-7905.
44. Rampi, M. A.; Whitesides, G. M. Chem. Phys. 2002, 281, 373-391.
45. Slowinski, K.; Chamberlin, R. V.; Miller, C. J.; Majda, M. J. Am. Chem. Soc. 1997, 119, 11910-11919.
46. If the whole system, after assembly, is immersed in D1 water or in hexane, (to check for possible influence of residual solvent, esp. on the effects of scan rate and on hysteresis by using a polar and an apolar solvent) essentially the same NDR behavior is observed as for the dry system.
47. Muskal, N.; Turyan, I.; Mandler, D. J. Electroanal. Chem. 1996, 409, 131-136.
48. -5 M (cf Muskal et al.47). Monolayer rearrangement (and ordering) then occurs after initial adsorption. This can be outside the solvent (as for the dry NDR measurements) or in the solvent (as for the wet electrochemistry experiments). For the dry measurements, we preferred shorter adsorption times to minimize solvent exposure as this improved reproducibility. For the wet electrochemistry measurements this was not an issue.
49. Coverages of 75-100% were found for the small disulfides, used in Bruening et al.,41 on Au and of 75% for a disulfide with one palmitoyl group.
50. Gershewitz, O.; Grinstein, M.; Sukenik, C. N.; Regev, K.; Ghabboun, J.; Cahen, D. J. Phys. Chem. B 2004, 108, 664-672.
51. Stankovich, M. T.; Bard, A. J. J. Electronal. Chem. 1977, 75, 487-505.
52. This proposed mechanism is based on the one for binding cystine to mercury in solution, given in Stankovich et al.51
53. x layer.
54. The PVR value is the ratio of the peak and the valley currents that occur at the beginning and the end of the range over which the system shows negative differential resistance.
55. The time delay between each voltage scan was 2 min.
56. 3.
57. Simmons, J. G. J. Appl. Phys. 1964, 35, 2655.
58. x layer). The simulations show that the tunneling current is 8 times lower for the wider barrier.
59. We define a delay time as the interval time between sequences of voltage scans.
60. Ulman, A.; Evans, S. D.; Shnidmany, Y.; Sharma, R.; Eilers, J. E. Adv. Colloid Interface Sci. 1992, 39, 175-224.
61. Holmlin, R. E.; Haag, R.; Chabinyc, M. L.; Ismagilov, R. F.; Cohen, A.; Terfort, A.; Rampi, M. A.; Whitesides, G. M. J. Am. Chem. Soc. 2001, 123, 5075-5085.
62. Gartsman, K.; Cahen, D.; Kadyshevitch, A.; Libman, J.; Moav, T.; Naaman, R.; Shanzer, A.; Umansky, V.; Vilan, A. Chem. Phys. Lett. 1998, 283, 301-306.
63. Stuve, E. M.; Krasnopoler, A.; Sauer, D. E. Surf. Sci. 1995, 335, 177-185.
64. Trasatti, S. Electrochim. Acta 1991, 36, 1659-1667.
65. x is about 0.5 V. After adsorption of the molecules the CPD decreases to < 0.2 V.6
66. 3-terminated disulfide molecules. We assume that the reduction potential for the other molecules in the series is similar.
67. x and 2.5 nm as the length of, the molecules.
68. Since one side of the interface is a semiconductor, extra charge at the interface will normally lead to realignment of the semiconductor energy band positions, with respect to the metal Fermi level. This will change the band bending and the barrier height for electron transport from the metal toward the semiconductor. However, here the reduction reaction occurs at forward bias potentials that are much higher than the barrier height, which means that no depletion layer is left in the semiconductor. Therefore, we can assume that the observed NDR does not result from changes in the metal/semiconductor barrier heights.
69. 2N.
70. Stevenson, K. J.; Mitchell, M.; White, H. S. J. Phys. Chem. B 1998, 102, 1235-1240.
71. x length, 1.2 and 2.4 nm as the lengths of the short and the long molecules (without S), respectively. For the Hg-S bond we took 5.5 as the dielectric constant and 0.25 nm as the bond length.
72. Koryta, J.; Pradac, J. J. Electroanal. Chem. 1968, 17, 177-183.
73. Koryta, J.; Pradac, J. J. Electroanal. Chem. 1968, 17, 185-189.
74. Haran, A.; Waldeck, D.; Naaman, R.; Moons, E.; Cahen, D. Science 1994, 263, 948-950.
75. Taylor, J.; Brandbyge, M.; Stokobro, K. Phys. Rev. Lett. 2002, 89, 138301.
76. Kornilovitch, P. E.; Bratkovsky, A. M.; Williams, S. R. Phys. Rev. B. 2002, 66, 165436.
77. Alloway, D. M.; Hofmann, M.; Smith, D. L.; Gruhn, N. E.; Graham, A. L.; Colorado, R. J.; Wysocki, V. H.; Lee, R.; Lee, P. A.; Armstrong, N. R. J. Phys. Chem. B 2003, 107, 11690-11699.
78. Because of the negative charges on the disulfide molecules after bond breaking and reduction, their HOMO-LUMO gap will decrease.
79. Troisi, A.; Ratner, M. A. J. Am. Chem. Soc 2002, 124, 14528-14529.