Structural and electrical properties of flip chip laminated metal-molecule-silicon structures varying molecular backbone and atomic tether

Journal of Physical Chemistry C

Volumn 115, Issue 49, 2011, Pages 24353-24365

  Coll, Mariona ^a,b   Gergel Hackett, Nadine ^a,c   Richter, Curt A ^a   Hacker, Christina A ^a  

^a NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^c MARY BALDWIN COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION INFRARED SPECTROSCOPY; AMBIENT CONDITIONS; CRITICAL FACTORS; CURRENT-VOLTAGE MEASUREMENTS; DIELECTRIC INTEGRITY; ELECTRICAL CONTACTS; ELECTRICAL INTEGRITY; ELECTRICAL STRUCTURES; FLIP CHIP; FUNCTIONALIZED; JUNCTION FORMATION; LOW COSTS; METAL ELECTRODES; MOLECULAR ARCHITECTURE; MOLECULAR JUNCTION; MOLECULAR TERMINALS; NANO SCALE; NANOELECTRONIC ARCHITECTURE; NON DESTRUCTIVE; ORGANIC MOLECULES; ORGANIC MONOLAYERS; PRESSURE AND TEMPERATURE; SILICON SUBSTRATES; STRUCTURAL AND ELECTRICAL PROPERTIES; SURFACE FREE ENERGY;

AROMATIC COMPOUNDS; ELECTRIC PROPERTIES; ELECTRODES; GOLD; INFRARED SPECTROSCOPY; IODINE; LAMINATING; LITHOGRAPHY; METALS; MOLECULES; NANOTECHNOLOGY; OLEFINS; SELF ASSEMBLED MONOLAYERS; VANADIUM;

CRYSTAL ATOMIC STRUCTURE;

EID: 83455213393     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp208275c     Document Type: Article

References (147)

1. Aviram, A. Molecules for Memory, Logic, and Amplification J. Am. Chem. Soc. 1988, 110 (17) 5687-5692
2. Lu, W.; Lieber, C. M. Nanoelectronics from the bottom up Nat. Mater. 2007, 6 (11) 841-850
3. Tour, J. M.; Kozaki, M.; Seminario, J. M. Molecular scale electronics: A synthetic/computational approach to digital computing J. Am. Chem. Soc. 1998, 120 (33) 8486-8493
4. Har-Lavan, R.; Ron, I.; Thieblemont, F.; Cahen, D. Toward metal-organic insulator-semiconductor solar cells, based on molecular monolayer self-assembly on n-Si Appl. Phys. Lett. 2009, 94 (4) 043308
5. Schmidt-Mende, L.; Fechtenkotter, A.; Mullen, K.; Moons, E.; Friend, R. H.; MacKenzie, J. D. Self-organized discotic liquid crystals for high-efficiency organic photovoltaics Science 2001, 293 (5532) 1119-1122
6. Kovalenko, M. V.; Scheele, M.; Talapin, D. V. Colloidal Nanocrystals with Molecular Metal Chalcogenide Surface Ligands Science 2009, 324 (5933) 1417-1420
7. Torsi, L.; Dodabalapur, A.; Rothberg, L. J.; Fung, A. W. P.; Katz, H. E. Intrinsic transport properties and performance limits of organic field-effect transistors Science 1996, 272 (5267) 1462-1464
8. Cattani-Scholz, A.; Pedone, D.; Dubey, M.; Neppl, S.; Nickel, B.; Feulner, P.; Schwartz, J.; Abstreiter, G.; Tornow, M. Organophosphonate-based PNA-functionalization of silicon nanowires for label-free DNA detection ACS Nano 2008, 2 (8) 1653-1660
9. Pike, A. R.; Lie, L. H.; Eagling, R. A.; Ryder, L. C.; Patole, S. N.; Connolly, B. A.; Horrocks, B. R.; Houlton, A. DNA on silicon devices: On-chip synthesis, hybridization, and charge transfer Angew. Chem., Int. Ed. 2002, 41 (4) 615-617
10. Stewart, M. P.; Maya, F.; Kosynkin, D. V.; Dirk, S. M.; Stapleton, J. J.; McGuiness, C. L.; Allara, D. L.; Tour, J. M. Direct covalent grafting of conjugated molecules onto Si, GaAs, and Pd surfaces from aryidiazonium salts J. Am. Chem. Soc. 2004, 126 (1) 370-378
11. Aswal, D. K.; Lenfant, S.; Guerin, D.; Yakhmi, J. V.; Vuillaume, D. Self assembled monolayers on silicon for molecular electronics Anal. Chim. Acta 2006, 568 (1-2) 84-108
12. Vuillaume, D.; Boulas, C.; Collet, J.; Allan, G.; Delerue, C. Electronic structure of a heterostructure of an alkylsiloxane self-assembled monolayer on silicon Phys. Rev. B 1998, 58 (24) 16491-16498
13. Vilan, A.; Yaffe, O.; Biller, A.; Salomon, A.; Kahn, A.; Cahen, D. Molecules on Si: Electronics with Chemistry Adv. Mater. 2010, 22 (2) 140-159
14. Rakshit, T.; Liang, G. C.; Ghosh, A. W.; Datta, S. Silicon-based molecular electronics Nano Lett. 2004, 4 (10) 1803-1807
15. McCreery, R. L.; Bergren, A. J. Progress with Molecular Electronic Junctions: Meeting Experimental Challenges in Design and Fabrication Adv. Mater. 2009, 21 (43) 4303-4322
16. McCreery, R. L. Molecular electronic junctions Chem. Mater. 2004, 16 (23) 4477-4496
17. Ranganathan, S. S., I.; Anariba, F.; McCreery, R. L. Covalently Bonded Organic Monolayers on a Carbon Substrate: A New Paradigm for Molecular Electronics Nano Lett. 2001, 1 (9) 491-494
18. Coll, M.; Miller, L. H.; Richter, L. J.; Hines, D. R.; Jurchescu, O. D.; Gergel-Hackett, N.; Richter, C. A.; Hacker, C. A. Formation of Silicon-Based Molecular Electronic Structures Using Flip-Chip Lamination J. Am. Chem. Soc. 2009, 131 (34) 12451-12457
19. Wagner, P.; Hegner, M.; Guntherodt, H. J.; Semenza, G. Formation and in-Situ Modification of Monolayers Chemisorbed on Ultraflat Template-Stripped Gold Surfaces Langmuir 1995, 11 (10) 3867-3875
20. Weiss, E. A.; Chiechi, R. C.; Kaufman, G. K.; Kriebel, J. K.; Li, Z. F.; Duati, M.; Rampi, M. A.; Whitesides, G. M. Influence of defects on the electrical characteristics of mercury-drop junctions: Self-assembled monolayers of n-alkanethiolates on rough and smooth silver J. Am. Chem. Soc. 2007, 129 (14) 4336-4349
21. Mahapatro, A. K.; Scott, A.; Manning, A.; Janes, D. B. Gold surface with sub-nm roughness realized by evaporation on a molecular adhesion monolayer Appl. Phys. Lett. 2006, 88 (15) 151917
22. Dumas, P.; Chabal, Y. J.; Jakob, P. Morphology of Hydrogen-Terminated Si(111) and Si(100) Surfaces Upon Etching in Hf and Buffered-Hf Solutions Surf. Sci. 1992, 269, 867-878
23. Higashi, G. S.; Becker, R. S.; Chabal, Y. J.; Becker, A. J. Comparison of Si(111) Surfaces Prepared Using Aqueous-Solutions of Nh4f Versus Hf Appl. Phys. Lett. 1991, 58 (15) 1656-1658
24. Li, X. L.; He, J.; Hihath, J.; Xu, B. Q.; Lindsay, S. M.; Tao, N. J. Conductance of single alkanedithiols: Conduction mechanism and effect of molecule-electrode contacts J. Am. Chem. Soc. 2006, 128 (6) 2135-2141
25. Tao, N. J. Electron transport in molecular junctions Nat. Nanotechnol. 2006, 1 (3) 173-181
26. Venkataraman, L.; Klare, J. E.; Tam, I. W.; Nuckolls, C.; Hybertsen, M. S.; Steigerwald, M. L. Single-molecule circuits with well-defined molecular conductance Nano Lett. 2006, 6 (3) 458-462
27. Selzer, Y.; Salomon, A.; Cahen, D. The importance of chemical bonding to the contact for tunneling through alkyl chains J. Phys. Chem. B 2002, 106 (40) 10432-10439
28. Quek, S. Y.; Kamenetska, M.; Steigerwald, M. L.; Choi, H. J.; Louie, S. G.; Hybertsen, M. S.; Neaton, J. B.; Venkataraman, L. Mechanically controlled binary conductance switching of a single-molecule junction Nat. Nanotechnol. 2009, 4 (4) 230-234
29. Venkataraman, L.; Park, Y. S.; Whalley, A. C.; Nuckolls, C.; Hybertsen, M. S.; Steigerwald, M. L. Electronics and chemistry: Varying single-molecule junction conductance using chemical substituents Nano Lett. 2007, 7 (2) 502-506
30. Hacker, C. A. Modifying electron transfer at the silicon-molecule interfance using atomic tethers Solid-State Electron. 2010, 54 (12) 1657-1664
31. Nitzan, A.; Galperin, M.; Ingold, G. L.; Grabert, H. On the electrostatic potential profile in biased molecular wires J. Chem. Phys. 2002, 117 (23) 10837-10841
32. Rissner, F.; Egger, D. A.; Romaner, L.; Heimel, G.; Zojer, E., The Electronic Structure of Mixed Self-Assembled Monolayers. ACS Nano 4 (11), 6735-6746
33. Gergel-Hackett, N.; Aguilar, I.; Richter, C. A. Engineering the Electron Transport of Silicon-Based Molecular Electronic Devices via Molecular Dipoles J. Phys. Chem. C 2010, 114 (49) 21708-21714
34. Venkataraman, L.; Klare, J. E.; Nuckolls, C.; Hybertsen, M. S.; Steigerwald, M. L. Dependence of single-molecule junction conductance on molecular conformation Nature 2006, 442 (7105) 904-907
35. Beebe, J. M.; Kim, B.; Frisbie, C. D.; Kushmerick, J. G. Measuring relative barrier heights in molecular electronic junctions with transition voltage spectroscopy ACS Nano 2008, 2 (5) 827-832
36. Choi, S. H.; Kim, B.; Frisbie, C. D. Electrical resistance of long conjugated molecular wires Science 2008, 320 (5882) 1482-1486
37. Segev, L.; Salomon, A.; Natan, A.; Cahen, D.; Kronik, L.; Amy, F.; Chan, C. K.; Kahn, A. Electronic structure of Si(111)-bound alkyl monolayers: Theory and experiment Phys. Rev. B 2006, 74 (16) 165323
38. McGuiness, C. L.; Blasini, D.; Masejewski, J. P.; Uppili, S.; Cabarcos, O. M.; Smilgies, D.; Allara, D. L. Molecular Self-Assembly at Bare Semiconductor Surfaces: Characterization of a Homologous Series of n-Alkanethiolate Monolayers on GaAs(001) ACS Nano 2007, 1 (1) 30-49
39. McGuiness, C. L.; Shaporenko, A.; Zharnikov, M.; Walker, A. V.; Allara, D. L. Molecular Self-Assembly at Bare Semiconductor Surfaces: Investigation of the Chemical and Electronic Properties of the Alkanethiolateâ̂ GaAs(001) Interface J. Phys. Chem. C 2007, 111 (11) 4226-4234
40. Ishizaki, T.; Saito, N.; SunHyung, L.; Ishida, K.; Takai, O. Study of Alkyl Organic Monolayers with Different Molecular Chain Lengths Directly Attached to Silicon Langmuir 2006, 22 (24) 9962-9966
41. Schreiber, F. Structure and growth of self-assembling monolayers Prog. Surf. Sci. 2000, 65 (5-8) 151-256
42. Maldonado, S.; Plass, K. E.; Knapp, D.; Lewis, N. S. Electrical Properties of Junctions between Hg and Si(111) Surfaces Functionalized with Short-Chain Alkyls J. Phys. Chem. C 2007, 111 (48) 17690-17699
43. Hacker, C. A.; Richter, C. A.; Gergel-Hackett, N.; Richter, L. J. Origin of differing reactivities of aliphatic chains on H-Si(111) and oxide surfaces with metal J. Phys. Chem. C 2007, 111 (26) 9384-9392
44. Hacker, C. A.; Anderson, K. A.; Richter, L. J.; Richter, C. A. Comparison of Si-O-C interfacial bonding of alcohols and aldehydes on Si(111) formed from dilute solution with ultraviolet irradiation Langmuir 2005, 21 (3) 882-889
45. Richter, C. A.; Hacker, C. A.; Richter, L. J.; Vogel, E. M. Molecular devices formed by direct monolayer attachment to silicon Solid-State Electron. 2004, 48 (10-11) 1747-1752
46. Hurley, P. T.; Ribbe, A. E.; Buriak, J. M. Nanopatterning of alkynes on hydrogen-terminated silicon surfaces by scanning probe-induced cathodic electrografting J. Am. Chem. Soc. 2003, 125 (37) 11334-11339
47. Wacaser, B. A.; Maughan, M. J.; Mowat, I. A.; Niederhauser, T. L.; Linford, M. R.; Davis, R. C. Chemomechanical surface patterning and functionalization of silicon surfaces using an atomic force microscope Appl. Phys. Lett. 2003, 82 (5) 808-810
48. Buriak, J. M. Organometallic chemistry on silicon and germanium surfaces Chem. Rev. 2002, 102 (5) 1271-1308
49. Miramond, C.; Vuillaume, D. 1-octadecene monolayers on Si(111) hydrogen-terminated surfaces: Effect of substrate doping J. Appl. Phys. 2004, 96 (3) 1529-1536
50. Richter, C. A.; Hacker, C. A.; Richter, L. J. Electrical and spectroscopic characterization of metal/monolayer/Si devices J. Phys. Chem. B 2005, 109 (46) 21836-21841
51. Allongue, P.; de Villeneuve, C. H.; Cherouvrier, G.; Cortes, R.; Bernard, M. C. Phenyl layers on H-Si(111) by electrochemical reduction of diazonium salts: monolayer versus multilayer formation J. Electroanal. Chem. 2003, 550, 161-174
52. Scott, A.; Hacker, C. A.; Janes, D. B. In situ structural characterization of metal-molecule-silicon junctions using backside infrared spectroscopy J. Phys. Chem. C 2008, 112 (36) 14021-14026
53. He, T.; Ding, H. J.; Peor, N.; Lu, M.; Corley, D. A.; Chen, B.; Ofir, Y.; Gao, Y. L.; Yitzchaik, S.; Tour, J. M. Silicon/molecule interfacial electronic modifications J. Am. Chem. Soc. 2008, 130 (5) 1699-1710
54. Hunger, R.; Jaegermann, W.; Merson, A.; Shapira, Y.; Pettenkofer, C.; Rappich, J. Electronic structure of methoxy-, bromo-, and nitrobenzene grafted onto Si(111) J. Phys. Chem. B 2006, 110 (31) 15432-15441
55. Anariba, F.; DuVall, S. H.; McCreery, R. L. Mono-and multilayer formation by diazonium reduction on carbon surfaces monitored with atomic force microscopy "scratching" Anal. Chem. 2003, 75 (15) 3837-3844
56. Haick, H.; Cahen, D. Contacting organic molecules by soft methods: Towards molecule-based electronic devices Acc. Chem. Res. 2008, 41 (3) 359-366
57. Loo, Y. L.; Lang, D. V.; Rogers, J. A.; Hsu, J. W. P. Electrical contacts to molecular layers by nanotransfer printing Nano Lett. 2003, 3 (7) 913-917
58. Hacker, C. A.; Coll, M.; Richter, C. A. Metrology of Molecular Devices made by Flip Chip Lamination Electrochem. Soc. Trans. 2010, 28, 549-562
59. Jung, D. R.; Czanderna, A. W. Chemical and Physical Interactions at Metal Self-Assembled Organic Monolayer Interfaces Crit. Rev. Solid State Mater. Sci. 1994, 19 (1) 1-54
60. Stewart, D. R.; Ohlberg, D. A. A.; Beck, P. A.; Chen, Y.; Williams, R. S.; Jeppesen, J. O.; Nielsen, K. A.; Stoddart, J. F. Molecule-independent electrical switching in Pt/organic monolayer/Ti devices Nano Lett. 2004, 4 (1) 133-136
61. Tai, Y.; Shaporenko, A.; Eck, W.; Grunze, M.; Zharnikov, M. Abrupt change in the structure of self-assembled monolayers upon metal evaporation Appl. Phys. Lett. 2004, 85 (25) 6257-6259
62. Walker, A. V.; Tighe, T. B.; Cabarcos, O. M.; Reinard, M. D.; Haynie, B. C.; Uppili, S.; Winograd, N.; Allara, D. L. The dynamics of noble metal atom penetration through methoxy-terminated alkanethiolate monolayers J. Am. Chem. Soc. 2004, 126 (12) 3954-3963
63. de Boer, B.; Frank, M. M.; Chabal, Y. J.; Jiang, W. R.; Garfunkel, E.; Bao, Z. Metallic contact formation for molecular electronics: interactions between vapor-deposited metals and self-assembled monolayers of conjugated mono-and dithiols Langmuir 2004, 20 (5) 1539-1542
64. Hooper, A.; Fisher, G. L.; Konstadinidis, K.; Jung, D.; Nguyen, H.; Opila, R.; Collins, R. W.; Winograd, N.; Allara, D. L. Chemical effects of methyl and methyl ester groups on the nucleation and growth of vapor-deposited aluminum films J. Am. Chem. Soc. 1999, 121 (35) 8052-8064
65. Walker, A. V.; Tighe, T. B.; Stapleton, J.; Haynie, B. C.; Upilli, S.; Allara, D. L.; Winograd, N. Interaction of vapor-deposited Ti and Au with molecular wires Appl. Phys. Lett. 2004, 84 (20) 4008-4010
66. Liu, Y. J.; Yu, H. Z. Molecular passivation of mercury-silicon (p-type) diode junctions: Alkylation, oxidation, and alkylsilation J. Phys. Chem. B 2003, 107 (31) 7803-7811
67. Salomon, A.; Bocking, T.; Gooding, J. J.; Cahen, D. How Important is the Interfacial Chemical Bond for Electron Transport through Alkyl Chain Monolayers Nano Lett. 2006, 6 (12) 2873-2876
68. Haick, H.; Niitsoo, O.; Ghabboun, J.; Cahen, D. Electrical contacts to organic molecular films by metal evaporation: Effect of contacting details J. Phys. Chem. C 2007, 111 (5) 2318-2329
69. Vilan, A.; Ghabboun, J.; Cahen, D. Molecule-metal polarization at rectifying GaAs interfaces J. Phys. Chem. B 2003, 107 (26) 6360-6376
70. Stein, N.; Korobko, R.; Yaffe, O.; Lavan, R. H.; Shpaisman, H.; Tirosh, E.; Vilan, A.; Cahen, D. Nondestructive Contact Deposition for Molecular Electronics: Si-Alkyl//Au Junctions J. Phys. Chem. C 2010, 114 (29) 12769-12776
71. Shimizu, K. T.; Fabbri, J. D.; Jelincic, J. J.; Melosh, N. A. Soft deposition of large-area metal contacts for molecular electronics Adv. Mater. 2006, 18 (12) 1499-1504
72. Stein, N.; Korobko, R.; Yaffe, O.; Lavan, R. H.; Shpaisman, H.; Tirosh, E.; Vilan, A.; Cahen, D. Nondestructive Contact Deposition for Molecular Electronics: Si-Alkyl//Au Junctions J. Phys. Chem. C 2010, 114 (29) 12769-12776
73. Coll, M.; Goetz, K. P.; Conrad, B. R.; Hacker, C. A.; Gundlach, D. J.; Richter, C. A.; Jurchescu, O. D. Flip chip lamination to electrically contact organic single crystals on flexible substrates Appl. Phys. Lett. 2011, 98, 16
74. Bain, C. D.; Troughton, E. B.; Tao, Y. T.; Evall, J.; Whitesides, G. M.; Nuzzo, R. G. Formation of Monolayer Films by the Spontaneous Assembly of Organic Thiols from Solution onto Gold J. Am. Chem. Soc. 1989, 111 (1) 321-335
75. Richter, C. A.; Hacker, C. A.; Richter, L. J.; Kirillov, O. A.; Suehle, J. S.; Vogel, E. M. Interface characterization of molecular-monolayer/SiO2 based molecular junctions Solid-State Electron. 2006, 50 (6) 1088-1096
76. de Boer, B.; Meng, H.; Perepichka, D. F.; Zheng, J.; Frank, M. M.; Chabal, Y. J.; Bao, Z. N. Synthesis and characterization of conjugated mono-and dithiol oligomers and characterization of their self-assembled monolayers Langmuir 2003, 19 (10) 4272-4284
77. Weckenmann, U.; Mittler, S.; Naumann, K.; Fischer, R. A. Ordered self-assembled monolayers of 4,4 ′-biphenyldithiol on polycrystalline silver: Suppression of multilayer formation by addition of tri-n-butylphosphine Langmuir 2002, 18 (14) 5479-5486
78. Coll, M.; Richter, C. A.; Hacker, C. A. Thermal stability of confined flip-chip laminated omega-functionalized monolayers J. Vac. Sci. Technol. B 2009, 27 (6) 2826-2831
79. Snyder, R. G.; Strauss, H. L.; Elliger, C. A. C-H Stretching Modes and the Structure of Normal-Alkyl Chains 0.1. Long, Disordered Chains J. Phys. Chem. 1982, 86 (26) 5145-5150
80. Peanasky, J. S.; McCarley, R. L. Surface-confined monomers on electrode surfaces. 4. Electrochemical and spectroscopic characterization of undec-10-ene-1-thiol self-assembled monolayers on Au Langmuir 1998, 14 (1) 113-123
81. Greenler, R. G. Infrared Study of Adsorbed Molecules on Metal Surfaces by Reflection Techniques J. Chem. Phys. 1966, 44 (1) 310-315
82. Higashi, G. S.; Chabal, Y. J.; Trucks, G. W.; Raghavachari, K. Ideal Hydrogen Termination of the Si-(111) Surface Appl. Phys. Lett. 1990, 56 (7) 656-658
83. Amy, S. R.; Michalak, D. J.; Chabal, Y. J.; Wielunski, L.; Hurley, P. T.; Lewis, N. S. Investigation of the reactions during alkylation of chlorine-terminated silicon (111) surfaces J. Phys. Chem. C 2007, 111 (35) 13053-13061
84. Michalak, D. J.; Rivillon, S.; Chabal, Y. J.; Esteve, A.; Lewis, N. S. Infrared spectroscopic investigation of the reaction of hydrogen-terminated, (111)-oriented, silicon surfaces with liquid methanol J. Phys. Chem. B 2006, 110 (41) 20426-20434
85. Linford, M. R.; Fenter, P.; Eisenberger, P. M.; Chidsey, C. E. D. Alkyl Monolayers on Silicon Prepared from 1-Alkenes and Hydrogen-Terminated Silicon J. Am. Chem. Soc. 1995, 117 (11) 3145-3155
86. Webb, L. J.; Rivillon, S.; Michalak, D. J.; Chabal, Y. J.; Lewis, N. S. Transmission infrared spectroscopy of methyl-and ethyl-terminated silicon(111) surfaces J. Phys. Chem. B 2006, 110 (14) 7349-7356
87. Sieval, A. B.; van den Hout, B.; Zuilhof, H.; Sudholter, E. J. R. Molecular modeling of alkyl monolayers on the Si(111) surface Langmuir 2000, 16 (7) 2987-2990
88. Weldon, M. K.; Marsico, V. E.; Chabal, Y. J.; Hamann, D. R.; Christman, S. B.; Chaban, E. E. Infrared spectroscopy as a probe of fundamental processes in microelectronics: Silicon wafer cleaning and bonding Surf. Sci. 1996, 368, 163-178
89. Liu, Y. J.; Wang, Z. G.; Suo, Y. R. Theoretical study on the mechanism for the addition reaction of SiH3 with propylene and acetic acid J. Phys. Chem. A 2006, 110 (45) 12439-12442
90. Asanuma, H.; Lopinski, G. P.; Yu, H. Z. Kinetic control of the photochemical reactivity of hydrogen-terminated silicon with bifunctional molecules Langmuir 2005, 21 (11) 5013-5018
91. Boukherroub, R.; Wayner, D. D. M. Controlled Functiontalization and Multistep Chemical Manipulation of Covalently Modified Si (111) Surfaces J. Am. Chem. Soc. 1999, 121 (49) 11513-11515
92. Carpick, R. W.; Salmeron, M. Scratching the surface: Fundamental investigations of tribology with atomic force microscopy Chem. Rev. 1997, 97 (4) 1163-1194
93. Nuzzo, R. G.; Dubois, L. H.; Allara, D. L. Fundamental-Studies of Microscopic Wetting on Organic-Surfaces 0.1. Formation and Structural Characterization of a Self-Consistent Series of Polyfunctional Organic Monolayers J. Am. Chem. Soc. 1990, 112 (2) 558-569
94. Arnold, R.; Azzam, W.; Terfort, A.; Woll, C. Preparation, Modification, and Crystallinity of Aliphatic and Aromatic Carboxylic Acid Terminated Self-Assembled Monolayers Langmuir 2002, 18 (10) 3980-3992
95. Bhushan, B.; Liu, H. W. Nanotribological properties and mechanisms of alkylthiol and biphenyl thiol self-assembled monolayers studied by AFM Phys. Rev. B 2001, 6324 (24) 245412
96. Schrader, M. E. Young-Dupre Revisited Langmuir 1995, 11 (9) 3585-3589
97. Green, J.-B. D.; McDermott, M. T.; Porter, M. D.; Siperko, L. M. Nanometer-Scale Mapping of Chemically Distinct Domains at Well-Defined Organic Interfaces Using Frictional Force Microscopy J. Phys. Chem. 1995, 99 (27) 10960-10965
98. Berg, O.; Klenerman, D. Vibrational spectroscopy of mechanically compressed monolayers J. Am. Chem. Soc. 2003, 125 (18) 5493-5500
99. Cicero, R. L.; Chidsey, C. E. D.; Lopinski, G. P.; Wayner, D. D. M.; Wolkow, R. A. Olefin additions on H-Si(111): Evidence for a surface chain reaction initiated at isolated dangling bonds Langmuir 2002, 18 (2) 305-307
100. Szori, M.; Jedlovszky, P.; Roeselova, M. Water adsorption on hydrophilic and hydrophobic self-assembled monolayers as proxies for atmospheric surfaces. A grand canonical Monte Carlo simulation study Phys. Chem. Chem. Phys. 2010, 12 (18) 4604-4616
101. Xiao, X. D.; Qian, L. M. Investigation of humidity-dependent capillary force Langmuir 2000, 16 (21) 8153-8158
102. Qian, L. M.; Tian, F.; Xiao, X. D. Tribological properties of self-assembled monolayers and their substrates under various humid environments Tribol. Lett. 2003, 15 (3) 169-176
103. Fadeev, A. Y.; McCarthy, T. J. Self-assembly is not the only reaction possible between alkyltrichlorosilanes and surfaces: Monomolecular and oligomeric covalently attached layers of dichloro-and trichloroalkylsilanes on silicon Langmuir 2000, 16 (18) 7268-7274
104. Boukherroub, R.; Petit, A.; Loupy, A.; Chazalviel, J. N.; Ozanam, F. Microwave-assisted chemical functionalization of hydrogen-terminated porous silicon surfaces J. Phys. Chem. B 2003, 107 (48) 13459-13462
105. Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.; Whitesides, G. M. Self-Assembled Monolayers of Thiolates on Metals as a Form of Nanotechnology Chem. Rev. 2005, 105 (4) 1103-1170
106. Niklewski, A.; Azzam, W.; Strunskus, T.; Fischer, R. A.; Woll, C. Fabrication of self-assembled monolayers exhibiting a thiol-terminated surface Langmuir 2004, 20 (20) 8620-8624
107. Jiang, W.; Zhitenev, N.; Bao, Z.; Meng, H.; Abusch-Magder, D.; Tennant, D.; Garfunkel, E. Structure and Bonding Issues at the Interface between Gold and Self-Assembled Conjugated Dithiol Monolayers Langmuir 2005, 21 (19) 8751-8757
108. Fenter, P.; Eisenberger, P.; Liang, K. S. Chain-Length Dependence of the Structures and Phases of Ch3(Ch2)N-1sh Self-Assembled on Au(111) Phys. Rev. Lett. 1993, 70 (16) 2447-2450
109. Porter, M. D.; Bright, T. B.; Allara, D. L.; Chidsey, C. E. D. Spontaneously Organized Molecular Assemblies 0.4. Structural Characterization of Normal-Alkyl Thiol Monolayers on Gold by Optical Ellipsometry, Infrared-Spectroscopy, and Electrochemistry J. Am. Chem. Soc. 1987, 109 (12) 3559-3568
110. Aliganga, A. K. A.; Duwez, A. S.; Mittler, S. Binary mixtures of self-assembled monolayers of 1,8-octanedithiol and 1-octanethiol for a controlled growth of gold nanoparticles Org. Electron. 2006, 7 (5) 337-350
111. Gergel-Hackett, N.; Zangmeister, C. D.; Hacker, C. A.; Richter, L. J.; Richter, C. A. Demonstration of molecular assembly on Si (100) for CMOS-compatible molecule-based electronic devices J. Am. Chem. Soc. 2008, 130 (13) 4259-4261
112. Brown, K. E.; Dlott, D. D. High-Pressure Raman Spectroscopy of Molecular Monolayers Adsorbed on a Metal Surface J. Phys. Chem. C 2009, 113 (14) 5751-5757
113. Kondoh, H.; Nambu, A.; Ehara, Y.; Matsui, F.; Yokoyama, T.; Ohta, T. Substrate dependence of self-assembly of alkanethiol: X-ray absorption fine structure study J. Phys. Chem. B 2004, 108 (34) 12946-12954
114. Tivanski, A. V.; Li, J. K.; Walker, G. C. Pressure-induced restructuring of a monolayer film nanojunction produces threshold and power law conduction Langmuir 2008, 24 (6) 2288-2293
115. Boukherroub, R. Chemical reactivity of hydrogen-terminated crystalline silicon surfaces Curr. Opin. Solid State Mater. Sci. 2005, 9 (1-2) 66-72
116. Eves, B. J.; Sun, Q. Y.; Lopinski, G. P.; Zuilhof, H. Photochemical attachment of organic monolayers onto H-terminated Si(111): Radical chain propagation observed via STM studies J. Am. Chem. Soc. 2004, 126 (44) 14318-14319
117. Hacker, C. A.; Batteas, J. D.; Garno, J. C.; Marquez, M.; Richter, C. A.; Richter, L. J.; van Zee, R. D.; Zangmeister, C. D. Structural and chemical characterization of monofluoro-substituted oligo(phenylene-ethynylene) thiolate self-assembled monolayers on gold Langmuir 2004, 20 (15) 6195-6205
118. Cornil, J.; Karzazi, Y.; Brédas, J. L. Negative Differential Resistance in Phenylene Ethynylene Oligomers J. Am. Chem. Soc. 2002, 124 (14) 3516-3517
119. Logdlund, M.; Salaneck, W. R.; Meyers, F.; Bredas, J. L.; Arbuckle, G. A.; Friend, R. H.; Holmes, A. B.; Froyer, G. Evolution of the Electronic-Structure in a Conjugated Polymer Series-Polyacetylene, Poly(P-Phenylene), and Poly(P-Phenylenevinylene) Macromolecules 1993, 26 (15) 3815-3820
120. Arnold, R.; Terfort, A.; Woll, C. Determination of molecular orientation in self-assembled monolayers using IR absorption intensities: The importance of grinding effects Langmuir 2001, 17 (16) 4980-4989
121. Vance, A. L.; Willey, T. M.; Nelson, A. J.; van Buuren, T.; Bostedt, C.; Terminello, L. J.; Fox, G. A.; Engelhard, M.; Baer, D. XAS and XPS Characterization of Monolayers Derived from a Dithiol and Structurally Related Disulfide-Containing Polyamides Langmuir 2002, 18 (21) 8123-8128
122. Tour, M. J.; 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. Self-Assembled Monolayers and Multilayers of Conjugated Thiols, α,ω-Dithiols, and Thioacetyl-Containing Adsorbates.Understanding Attachments between Potential Molecular Wires and Gold Surfaces J. Am. Chem. Soc. 1995, 117, 9529-9534
123. Tao, F.; Wang, Z. H.; Lai, Y. H.; Xu, G. Q. Attachment of styrene and phenylacetylene on si(111)-7 × 7: The influence of substitution groups on the reaction mechanism and formation of pi-conjugated skeletons J. Am. Chem. Soc. 2003, 125 (22) 6687-6696
124. Schwartz, M. P.; Ellison, M. D.; Coulter, S. K.; Hovis, J. S.; Hamers, R. J. Interaction of pi-conjugated organic molecules with pi-bonded semiconductor surfaces: Structure, selectivity, and mechanistic implications J. Am. Chem. Soc. 2000, 122 (35) 8529-8538
125. Coulter, S. K.; Schwartz, M. P.; Hamers, R. J. Sulfur atoms as tethers for selective attachment of aromatic molecules to silicon(001) surfaces J. Phys. Chem. B 2001, 105 (15) 3079-3087
126. Salomon, A.; Boecking, T.; Seitz, O.; Markus, T.; Amy, F.; Chan, C.; Zhao, W.; Cahen, D.; Kahn, A. What is the barrier for tunneling through alkyl monolayers? Results from n-and p-Si-Alkyl/Hg junctions Adv. Mater. 2007, 19 (3) 445-450
127. Thieblemont, F.; Seitz, O.; Vilan, A.; Cohen, H.; Salomon, E.; Kahn, A.; Cahen, D. Electronic Current Transport through Molecular Monolayers: Comparison between Hg/Alkoxy and Alkyl Monolayer/Si(100) Junctions Adv. Mater. 2008, 20 (20) 3931-3936
128. Yaffe, O.; Scheres, L.; Puniredd, S. R.; Stein, N.; Biller, A.; Lavan, R. H.; Shpaisman, H.; Zuilhof, H.; Haick, H.; Cahen, D.; Vilan, A. Molecular Electronics at Metal/Semiconductor Junctions. Si Inversion by Sub-Nanometer Molecular Films Nano Lett. 2009, 9 (6) 2390-2394
129. Mahapatro, A. K.; Scott, A.; Manning, A.; Janes, D. B. Gold surface with sub-nm roughness realized by evaporation on a molecular adhesion monolayer Appl. Phys. Lett. 2006, 88 (15) 3
130. Hsu, J. W. P.; Loo, Y. L.; Lang, D. V.; Rogers, J. A. Nature of electrical contacts in a metal-molecule-semiconductor system J. Vac. Sci. Technol. B 2003, 21 (4) 1928-1935
131. Vilan, A.; Yaffe, O.; Biller, A.; Salomon, A.; Kahn, A.; Cohen, D. Molecules on Si: Electronics with Chemistry Adv. Mater. 2010, 22 (2) 140-159
132. Stein, N.; Korobko, R.; Yaffe, O.; Har Lavan, R.; Shpaisman, H.; Tirosh, E.; Vilan, A.; Cahen, D. Nondestructive Contact Deposition for Molecular Electronics: Si-Alkyl//Au Junctions J. Phys. Chem. C 2010, 114 (29) 12769-12776
133. Salomon, A.; Backing, T.; Gooding, J. J.; Cahen, D. How Important Is the Interfacial Chemical Bond for Electron Transport through Alkyl Chain Monolayers? Nano Lett. 2006, 6 (12) 2873-2876
134. Beebe, J. M.; Kim, B.; Gadzuk, J. W.; Frisbie, C. D.; Kushmerick, J. G. Transition from direct tunneling to field emission in metal-molecule-metal junctions Phys. Rev. Lett. 2006, 97 (2) 026801
135. Salomon, A.; Boecking, T.; Chan, C. K.; Amy, F.; Girshevitz, O.; Cahen, D.; Kahn, A. How do electronic carriers cross Si-bound alkyl monolayers? Phys. Rev. Lett. 2005, 95 (26) 266807
136. Salomon, A.; Cahen, D.; Lindsay, S.; Tomfohr, J.; Engelkes, V. B.; Frisbie, C. D. Comparison of electronic transport measurements on organic molecules Adv. Mater. 2003, 15 (22) 1881-1890
137. Akkerman, H. B.; de Boer, B. Electrical conduction through single molecules and self-assembled monolayers J. Phys.: Condens. Matter 2008, 20 (1) 013001-013021
138. Hacker, C. A. Modifying electronic properties at the silicon-molecule interface using atomic tethers Solid-State Electron. 2010, 54 (12) 1657-1664
139. Scott, A.; Risko, C.; Valley, N.; Ratner, M. A.; Janes, D. B. Molecular modulation of Schottky barrier height in metal-molecule-silicon diodes: Capacitance and simulation results J. Appl. Phys. 2010, 107, 2
140. Himpsel, F. J.; Hollinger, G.; Pollak, R. A. Determination of the Fermi-Level Pinning Position at Si(111) Surfaces Phys. Rev. B 1983, 28 (12) 7014-7018
141. Monch, W. Semiconductor Surfaces and Interfaces; Springer-Verlag: Berlin, 1993.
142. Bent, S. F. Heads or Tails: Which Is More Important in Molecular Self-Assembly? Acs Nano 2007, 1 (1) 10-12
143. Segev, L.; Salomon, A.; Natan, A.; Cahen, D.; Kronik, L.; Amy, F.; Chan, C. K.; Kahn, A., Electronic structure of Si(111)-bound alkyl monolayers: Theory and experiment. Phys. Rev. B 2006, 74 (16),-.
144. Yu, L. H.; Gergel-Hackett, N.; Zangmeister, C. D.; Hacker, C. A.; Richter, C. A.; Kushmerick, J. G. Molecule-induced interface states dominate charge transport in Si-alkyl-metal junctions J. Phys.: Condens. Matter 2008, 20 (37) 5
145. Scott, A.; Janes, D. B. Gold/Molecule/p(+) Si Devices: Variable Temperature Electronic Transport IEEE Trans. Nanotechnol. 2010, 9 (4) 494-503
146. Engelkes, V. B.; Beebe, J. M.; Frisbie, C. D. Length-dependent transport in molecular junctions based on SAMs of alkanethiols and alkanedithiols: Effect of metal work function and applied bias on tunneling efficiency and contact resistance J. Am. Chem. Soc. 2004, 126 (43) 14287-14296
147. van der Marel, C.; Yidirim, M.; Stapert, H. R. Multilayer approach to the quantitative analysis of x-ray photoelectron spectroscopy results: Applications to ultrathin SiO2 on Si and to self-assembled monolayers on gold J. Vac. Sci. Technol. A 2005, 23 (5) 1456-1470