UV-initiated hydrosilylation on hydrogen-terminated silicon (111): Rate coefficient increase of two orders of magnitude in the presence of aromatic electron acceptors

Langmuir

Volumn 28, Issue 47, 2012, Pages 16285-16293

  Huck, Lawrence A ^a,b   Buriak, Jillian M ^a,b  

^a UNIVERSITY OF ALBERTA   (Canada)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC ADDITIVES; AROMATIC ELECTRONS; AROMATIC MOLECULES; ELECTRON TRANSFER; HYDROGEN-TERMINATED SILICON; MAXIMUM COVERAGE; ORDERS OF MAGNITUDE; PSEUDO-FIRST-ORDER; RATE COEFFICIENTS; REDUCTION POTENTIAL; SI (1 1 1); SI-C BOND FORMATION; SURFACE HOLES;

AROMATIC COMPOUNDS; HYDROGEN; HYDROSILYLATION; MOLECULES; MONOLAYERS; OLEFINS; PHYSISORPTION; SILICON;

AROMATIZATION;

EID: 84870168544     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la3035819     Document Type: Article

References (67)

1. Wolkow, R. A. Controlled Molecular Adsorption on Silicon: Laying a Foundation for Molecular Devices Annu. Rev. Phys. Chem. 1999, 50, 413-441
2. Vilan, A.; Yaffe, O.; Biller, A.; Salomon, A.; Kahn, A.; Cahen, D. Molecules on Si: Electronics with Chemistry Adv. Mater. 2010, 22, 140-159
3. Kachian, J. S.; Wong, K. T.; Bent, S. F. Periodic Trends in Organic Functionalization of Group IV Semiconductor Surfaces Acc. Chem. Res. 2010, 43, 346-355
4. Gooding, J. J.; Ciampi, S. The Molecular Level Modification of Surfaces: from Self-Assembled Monolayers to Complex Molecular Assemblies Chem. Soc. Rev. 2011, 40, 2704-2718
5. Buriak, J. M. Organometallic Chemistry of Silicon and Germanium Surfaces Chem. Rev. 2002, 102, 1271-1308
6. Ciampi, S.; Harper, J. B.; Gooding, J. J. Wet Chemical Routes to the Assembly of Organic Monolayers on Silicon Surfaces via the Formation of Si-C Bonds: Surface Preparation, Passivation and Functionalization Chem. Soc. Rev. 2010, 39, 2158-2183
7. Li, Y.; Calder, S.; Yaffe, O.; Cahen, D.; Haick, H.; Kronik, L.; Zuilhof, H. Hybrids of Organic Molecules and Flat, Oxide-Free Silicon: High-Density Monolayers, Electronic Properties, and Functionalization Langmuir 2012, 28, 9920-9929
8. Klingebiel, B.; Scheres, L.; Franzka, S.; Zuilhof, H.; Hartmann, N. Photothermal Micro- and Nanopatterning of Organic/Silicon Interfaces Langmuir 2010, 26, 6826-6831
9. Wagner, P.; Nock, S.; Spudich, J. A.; Volkmuth, W. D.; Chu, S.; Cicero, R. L.; Wade, C. P.; Linford, M. R.; Chidsey, C. E. D. Bioreactive Self-Assembled Monolayers on Hydrogen-Passivated Si(111) as a New Class of Atomically Flat Substrates for Biological Scanning Probe Microscopy J. Struct. Biol. 1997, 119, 189-201
10. Terry, J.; Mo, R.; Wigren, C.; Cao, R.; Mount, G.; Pianetta, P.; Linford, M. R.; Chidsey, C. E. D. Reactivity of the H-Si(111) Surface Nucl. Instrum. Methods Phys. Res. 1997, 133, 94-101
11. Cicero, R. L.; Linford, M. R.; Chidsey, C. E. D. Photoreactivity of Unsaturated Compounds with Hydrogen-Terminated Silicon(111) Langmuir 2000, 16, 5688-5695
12. Laarhoven, L. J. J.; Mulder, P.; Wayner, D. D. M. Determination of Bond Dissociation Enthalpies in Solution by Photoacoustic Calorimetry Acc. Chem. Res. 1999, 32, 342-349
13. Novikov, A. Experimental Measurement of Work Function in Doped Silicon Surfaces Solid-State Electron. 2010, 54, 8-13
14. Wang, X.; Ruther, R. E.; Streifer, J. A.; Hamers, R. J. UV-Induced Grafting of Alkenes to Silicon Surfaces: Photoemission versus Excitons J. Am. Chem. Soc. 2010, 132, 4048-4049
15. Huck, L. A.; Buriak, J. M. Toward a Mechanistic Understanding of Exciton-Mediated Hydrosilylation on Nanocrystalline Silicon J. Am. Chem. Soc. 2012, 134, 489-497
16. Shalev, H.; Evans, D. H. Solvation of Anion Radicals: Gas Phase vs Solution J. Am. Chem. Soc. 1989, 111, 2667-2674
17. Shirahata, N.; Yonezawa, T.; Seo, W.-S.; Koumoto, K. Photoinduced Cleavage of Alkyl Monolayers on Si Langmuir 2004, 20, 1517-1520
18. Uosaki, K.; Quayum, M. E.; Nihonyanagi, S.; Kondo, T. Decomposition Processes of an Organic Monolayer Formed on Si(111) via a Silicon-Carbon Bond Induced by Exposure to UV Irradiation or Ozone Langmuir 2004, 20, 1207-1212
19. Sun, Q.-Y.; de Smet, L. C. P. M.; van Lagen, B.; Giesbers, M.; Thüne, P. C.; van Engelenburg, J.; de Wolf, F. A.; Zuilhof, H.; Sudhölter, E. J. R. Covalently Attached Monolayers on Crystalline Hydrogen-Terminated Silicon: Extremely Mild Attachment by Visible Light J. Am. Chem. Soc. 2005, 127, 2514-2523
20. Good, R. J. Contact Angle, Wetting, And Adhesion: A Critical Review J. Adhes. Sci. Technol. 1992, 6, 1269-1302
21. Li, Y.-h.; Wang, D.; Buriak, J. M. Molecular Layer Deposition of Thiol-Ene Multilayers on Semiconductor Surfaces Langmuir 2010, 26, 1232-1238
22. Espenson, J. H. Chemical Kinetics and Reaction Mechanisms, 2 nd ed.; McGraw-Hill Book Co.: New York, 1995; pp 15-18.
23. Nichols, B. M.; Butler, J. E.; Russell, J. N., Jr.; Hamers, R. J. Photochemical Functionalization of Hydrogen-Terminated Diamond Surfaces: A Structural and Mechanistic Study J. Phys. Chem. B 2005, 109, 20938-20947
24. Webb, L. J.; Michalak, D. J.; Biteen, J. S.; Brunschwig, B. S.; Chan, A. S. Y.; Knapp, D. W.; Meyer, H. M., III; Nemanick, E. J.; Traub, M. C.; Lewis, N. S. High-Resolution Soft X-ray Photoelectron Spectroscopic Studies and Scanning Auger Microscopy Studies of the Air Oxidation of Alkylated Silicon(111) Surfaces J. Phys. Chem. B 2006, 110, 23450-23459
25. Paape, N.; Wei, W.; Bösmann, A.; Kolbeck, C.; Maier, F.; Steinrück, H.-P.; Wasserscheid, P.; Schulz, P. S. Chloroalkylsulfonate ionic liquids by ring opening of sultones with organic chloride salts Chem. Commun. 2008, 3867-3869
26. Luo, Y.-R. Comprehensive Handbook of Chemical Bond Energies; CRC Press: Boca Raton, FL, 2007; p 211.
27. Kariv-Miller, E.; Pacut, R. I.; Lehman, G. K. Organic Electroreductions at Very Negative Potentials Top. Curr. Chem. 1988, 148, 97-130
28. Magdesieva, T. V.; Shishkin, V. N.; Butin, K. P. Effect of Electrode Material on Reduction Potential of Polyhalobenzenes Zh. Obshch. Khim. 1991, 61, 2403-2405
29. Farwell, S. O.; Beland, F. A.; Geer, R. D. Reduction Pathways of Organohalogen Compounds. Part 1. Chlorinated Benzenes J. Electroanal. Chem. Interfacial Electrochem. 1975, 61, 303-313
30. Isse, A. A.; Lin, C. Y.; Coote, M. L.; Gennaro, A. Estimation of Standard Reduction Potentials of Halogen Atoms and Alkyl Halides J. Phys. Chem. B 2011, 115, 678-684
31. Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. Absolute Rate Constants for the Reaction of Triethylsilyl Radical with Organic Halides J. Am. Chem. Soc. 1982, 104, 5123-5127
32. Chatgilialoglu, C.; Ingold, K. U.; Scaiano, J. C. Absolute Rate Constants for the Addition of Triethylsilyl Radicals to Various Unsaturated Compounds J. Am. Chem. Soc. 1983, 105, 3292-3296
33. Spahr, M. E.; Palladino, T.; Wilhelm, H.; Würsig, A.; Goers, D.; Buqa, H.; Holzapfel, M.; Novák, P. Exfoliation of Graphite during Electrochemical Lithium Insertion in Ethylene Carbonate-Containing Electrolytes J. Electrochem. Soc. 2004, 151 (9) A1383-A1395
34. Gritzner, G. Solvent Effects on Half-Wave Potentials J. Phys. Chem. 1986, 90, 5478-5485
35. Totten, L. A.; Roberts, A. L. Calculated One- and Two-Electron Reduction Potentials and Related Molecular Descriptors for Reduction of Alkyl and Vinyl Halides in Water Crit. Rev. Environ. Sci. Technol. 2001, 31, 175-221
36. Chatgilialoglu, C.; Newcomb, M. Hydrogen Donor Abilities of the Group 14 Hydrides Adv. Organomet. Chem. 1999, 44, 67-112
37. Héberger, K.; Walbiner, M.; Fischer, H. Addition of Benzyl Radicals to Alkenes: The Role of Radical Deformation in the Transition State Angew. Chem., Int. Ed. Engl. 1992, 31, 635-636
38. Kira, M.; Hino, T.; Sakurai, H. An NMR Study of the Formation of Silyloxonium Ions by Using Tetrakis[3,5-bis(trifluoromethyl)phenyl]borate as Counteranion J. Am. Chem. Soc. 1992, 114, 6697-6700
39. +) Science 1993, 262, 402-404
40. Nishinaga, T.; Izukawa, Y.; Komatsu, K. The First Silatropylium Ion Stabilized by Rigid Frameworks: Preparation, Properties, and Some Reactions Tetrahedron 2001, 57, 3645-3656
41. Wang, Y.; Dorfman, L. M. Reactivity of Benzyl Cation and of Benzhydryl Cation with Alkenes in Solution: Initiation Step in Cationic Polymerization Macromolecules 1980, 13, 63-65
42. Hiratsuka, H.; Okamoto, T.; Kuroda, S.; Okutsu, T.; Maeoka, H.; Taguchi, M.; Yoshinaga, T. Photochemical reaction intermediates of benzyl chloride in condensed phase Res. Chem. Intermed. 2001, 27, 137-153
43. Stutz, J.; Ezell, M. J.; Ezell, A. A.; Finlayson-Pitts, B. J. Rate Constants and Kinetic Isotope Effects in the Reactions of Atomic Chlorine with n-Butane and Simple Alkenes at Room Temperature J. Phys. Chem. A 1998, 102, 8510-8519
44. Popoff, R. T. W.; Zavareh, A. A.; Kavanagh, K. L.; Yu, H.-Z. Reduction of Gold Penetration through Phenyl-Terminated Alkyl Monolayers on Silicon J. Phys. Chem. C 2012, 116, 17040-17047
45. Martínez, A.; Alonso, J. M.; Sansores, L. E.; Salcedo, R. Electronic Structure of Silicon Nanocrystals Passivated with Nitrogen and Chlorine J. Phys. Chem. C 2010, 114, 12427-12431
46. Ng, M.-F.; Sim, L. Y.; Da, H.; Jin, H.; Lim, K. H.; Yang, S.-W. Modulation of the Work Function of Silicon Nanowire by Chemical Surface Passivation: A DFT Study Theor. Chem. Acc. 2010, 127, 689-695
47. Johnson, E. R.; DiLabio, G. A. Theoretical Study of Dispersion Binding of Hydrocarbon Molecules to Hydrogen-Terminated Silicon(100)-2 × 1 J. Phys. Chem. C 2009, 113, 5681-5689
48. Bard, A. J.; Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications, 2 nd ed.; Wiley: New York, 2001; p 760.
49. Caldwell, J. W.; Kollman, P. A. Cation-φ Interactions: Nonadditive Effects Are Critical in Their Accurate Representation J. Am. Chem. Soc. 1995, 117, 4177-4178
50. Ma, J. C.; Dougherty, D. A. The Cation-φ Interaction Chem. Rev. 1997, 97, 1303-1324
51. Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: Sausalito, CA, 2006; pp 180-183.
52. Wheeler, S. E. Understanding Substituent Effects in Noncovalent Interactions Involving Aromatic Rings Acc. Chem. Res. 2012, 10.1021/ar300109n
53. Lambert, J. B.; Zhao, Y.; Zhang, S. M. Preparation of the First Tricoordinate Silyl Cation J. Phys. Org. Chem. 2001, 14, 370-379
54. Lambert, J. B.; Zhang, S.; Stern, C. L.; Huffman, J. C. Crystal Structure of a Silyl Cation with No Coordination to Anion and Distant Coordination to Solvent Science 1993, 260, 1917-1918
55. Kim, K.-C.; Reed, C. A.; Elliott, D. W.; Mueller, L. J.; Tham, F.; Lin, L.; Lambert, J. B. Crystallographic Evidence for a Free Silylium Ion Science 2002, 297, 825-827
56. + with the Aromatic Amino Acids, Phenylalanine, Tyrosine, and Tryptophan J. Am. Chem. Soc. 2004, 126, 14600-14610
57. Wiberg, K. B. The Interaction of Carbonyl Groups with Substituents Acc. Chem. Res. 1999, 32, 922-929
58. Bateman, J. E.; Eagling, R. D.; Horrocks, B. R.; Houlton, A. A Deuterium Labeling, FTIR, and Ab Initio Investigation of the Solution-Phase Thermal Reactions of Alcohols and Alkenes with Hydrogen-Terminated Silicon Surfaces J. Phys. Chem. B 2000, 104, 5557-5565
59. Langer, A.; Panarello, A.; Rivillon, S.; Vassylyev, O.; Khinast, J. G.; Chabal, Y. J. Controlled Silicon Surface Functionalization by Alkene Hydrosilylation J. Am. Chem. Soc. 2005, 127, 12798-12799
60. Zhong, Y. L.; Bernasek, S. L. Direct Photochemical Functionalization of Si(111) with Undecenol Langmuir 2011, 27, 1796-1802
61. Allan, G.; Delerue, C.; Lannoo, M.; Martin, E. Hydrogenic Impurity Levels, Dielectric Constant, and Coulomb Charging Effects in Silicon Crystallites Phys. Rev. B 1995, 52, 11982-11989
62. Scheres, L.; Giesbers, M.; Zuilhof, H. Organic Monolayers onto Oxide-Free Silicon with Improved Surface Coverage: Alkynes versus Alkenes Langmuir 2010, 26, 4790-4795
63. Michalak, D. J.; Amy, S. R.; Aureau, D.; Dai, M.; Estève, A.; Chabal, Y. J. Nanopatterning Si(111) Surfaces as a Selective Surface-Chemistry Route Nat. Mater. 2010, 9, 266-271
64. Fidélis, A.; Ozanam, F.; Chazalviel, J.-N. Fully Methylated, Atomically Flat (111) Silicon Surface Surf. Sci. 2000, 444, L7-L10
65. Zhang, Z.; Yates, J. T. Band Bending in Semiconductors: Chemical and Physical Consequences at Surfaces and Interfaces Chem. Rev. 2012, 112, 5520-5551
66. Nakamura, T.; Miyajima, K.; Hirata, N.; Matsumoto, T.; Morikawa, Y.; Tada, H.; Nakajima, A. Electronic Structure of Hydrogen-Terminated Silicon Surfaces [H-Si(111)] Studied by Two-Photon Photoemission Appl. Phys. A: Mater. Sci. Process. 2010, 98, 735-743
67. Rehm, J. M.; McLendon, G. L.; Fauchet, P. M. Conduction and Valence Band Edges of Porous Silicon Determined by Electron Transfer J. Am. Chem. Soc. 1996, 118, 4490-4491