Covalent attachment of diamondoid phosphonic acid dichlorides to tungsten oxide surfaces

Langmuir

Volumn 29, Issue 31, 2013, Pages 9790-9797

  Li, Fei Hua ^a   Fabbri, Jason D ^a   Yurchenko, Raisa I ^b   Mileshkin, Alexander N ^b   Hohman, J Nathan ^a   Yan, Hao ^a   Yuan, Hongyuan ^a   Tran, Ich C ^c   Willey, Trevor M ^c   Bagge Hansen, Michael ^c   Dahl, Jeremy E P ^a   Carlson, Robert M K ^a   Fokin, Andrey A ^b,d   Schreiner, Peter R ^d   Shen, Zhi Xun ^a   Melosh, Nicolas A ^a  

^a STANFORD UNIVERSITY   (United States)

^b NATIONAL TECHNICAL UNIVERSITY OF UKRAINE   (Ukraine)

^c LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

^d JUSTUS LIEBIG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON NANO-MATERIALS; ELECTROMECHANICAL SYSTEMS; ELECTRON PHONON SCATTERING; EXTREME ULTRAVIOLETS; FOURIER TRANSFORM INFRA REDS; NEGATIVE ELECTRON AFFINITY; PHOSPHONATE MONOLAYERS; TUNGSTEN OXIDE FILMS;

ELECTRON BEAM LITHOGRAPHY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; OXIDE FILMS; OXIDES; PHOTOELECTRONS; PHOTOEMISSION; TUNGSTEN COMPOUNDS; X RAY PHOTOELECTRON SPECTROSCOPY;

MONOLAYERS;

EID: 84881529983     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la401781e     Document Type: Article

References (60)

1. Dahl, J. E.; Liu, S. G.; Carlson, R. M. K. Isolation and Structure of Higher Diamondoids, Nanometer-sized Diamond Molecules Science 2003, 299, 96-9
2. Dahl, J. E. P.; Moldowan, J. M.; Wei, Z.; Lipton, P. A.; Denisevich, P.; Gat, R.; Liu, S.; Schreiner, P. R.; Carlson, R. M. K. Synthesis of Higher Diamondoids and Implications for Their Formation in Petroleum Angew. Chem., Int. Ed. 2010, 49, 9881-5
3. Krainsky, I. L.; Asnin, V. M. Negative Electron Affinity Mechanism for Diamond Surfaces Appl. Phys. Lett. 1998, 72, 2574
4. Drummond, N. D.; Williamson, A. J.; Needs, R. J.; Galli, G. Electron Emission from Diamondoids: A Diffusion Quantum Monte Carlo Study Phys. Rev. Lett. 2005, 096801, 1-4
5. Yang, W. L.; Fabbri, J. D.; Willey, T. M.; Lee, J. R. I.; Dahl, J. E.; Carlson, R. M. K.; Schreiner, P. R.; Fokin, A. A.; Tkachenko, B. A.; Fokina, N. A.; Meevasana, W.; Mannella, N.; Tanaka, K.; Zhou, X. J.; Van Buuren, T.; Kelly, M. A.; Hussain, Z.; Melosh, N. A.; Shen, Z.-X. Monochromatic Electron Photoemission from Diamondoid Monolayers Science 2007, 316, 1460-2
6. Clay, W. A.; Liu, Z.; Yang, W.; Fabbri, J. D.; Dahl, J. E. P.; Carlson, R. M. K.; Sun, Y.; Schreiner, P. R.; Fokin, A. A.; Tkachenko, B. A.; Fokina, N. A.; Pianetta, P. A.; Melosh, N. A.; Shen, Z.-X. Origin of the Monochromatic Photoemission Peak in Diamondoid Monolayers Nano Lett. 2008, 9, 57-61
7. Roth, S.; Leuenberger, D.; Osterwalder, J.; Dahl, J. E.; Carlson, R. M. K.; Tkachenko, B. A.; Fokin, A. A.; Schreiner, P. R.; Hengsberger, M. Negative-electron-affinity Diamondoid Monolayers as High-brilliance Source for Ultrashort Electron Pulses Chem. Phys. Lett. 2010, 495, 102-108
8. Clay, W. A.; Maldonado, J. R.; Pianetta, P. A.; Dahl, J. E. P.; Carlson, R. M. K.; Schreiner, P. R.; Fokin, A. A.; Tkachenko, B. A.; Melosh, N. A.; Shen, Z.-X. Photocathode Device Using Diamondoid and Cesium Bromide Films Appl. Phys. Lett. 2012, 101, 241605
9. Ishiwata, H.; Acremann, Y.; Scholl, A.; Rotenberg, E.; Hellwig, O.; Dobisz, E.; Doran, A.; Tkachenko, B. A.; Fokin, A. A.; Schreiner, P. R.; Dahl, J. E. P.; Carlson, R. M. K.; Melosh, N. A.; Shen, Z.-X.; Ohldag, H. Diamondoid Coating Enables Disruptive Approach for Chemical and Magnetic Imaging with 10 Nm Spatial Resolution Appl. Phys. Lett. 2012, 101, 1-5
10. Machuca, F.; Liu, Z.; Maldonado, J. R.; Coyle, S. T. Negative Electron Affinity Group III-nitride Photocathode Demonstrated as a High Performance Electron Source J. Vac. Sci. Technol., B 2004, 22, 3565-3569
11. Wang, Y.; Kioupakis, E.; Lu, X.; Wegner, D.; Yamachika, R.; Dahl, J. E. P.; Carlson, R. M. K.; Louie, S. G.; Crommie, M. F. Spatially Resolved Electronic and Vibronic Properties of Single Diamondoid Molecules Nat. Mater. 2007, 7, 38-42
12. Willey, T. M.; Fabbri, J. D.; Lee, J. R. I.; Schreiner, P. R.; Fokin, A. A.; Tkachenko, B. A.; Fokina, N. A.; Dahl, J. E. P.; Carlson, R. M. K.; Vance, A. L.; Yang, W.; Terminello, L. J.; Van Buuren, T.; Melosh, N. A. Near-edge X-ray Absorption Fine Structure Spectroscopy of Diamondoid Thiol Monolayers on Gold J. Am. Chem. Soc. 2008, 130, 10536-44
13. Hohman, J. N.; Claridge, S. A.; Kim, M.; Weiss, P. S. Cage Molecules for Self-assembly Mater. Sci. Eng., R 2010, 70, 188-208
14. Zhang, W.; Gao, B.; Yang, J.; Wu, Z.; Carravetta, V.; Luo, Y. Electronic Structure of Tetramantane-6-thiol on Gold and Silver Surfaces J. Chem. Phys. 2009, 130, 054705
15. Kim, M.; Hohman, J. N.; Morin, E. I.; Daniel, T. A.; Weiss, P. S. Self-Assembled Monolayers of 2-Adamantanethiol on Au {111}: Control of Structure and Displacement J. Phys. Chem. A 2009, 113, 3895-903
16. Flynn, N. T.; Tran, T. N. T.; Cima, M. J.; Langer, R. Long-Term Stability of Self-Assembled Monolayers in Biological Media Langmuir 2003, 19, 10909-10915
17. Sung, I.; Kim, D. Surface Damage Characteristics of Self-assembled Monolayers of Alkanethiols on Metal Surfaces Tribol. Lett. 2004, 17, 835-844
18. Schwertfeger, H.; Fokin, A. A.; Schreiner, P. R. Diamonds Are a Chemist's Best Friend: Diamondoid Chemistry Beyond Adamantane Angew. Chem., Int. Ed. 2007, 47, 1022-36
19. Linford, M. R.; Chidsey, C. E. D. Alkyl Monolayers Covalently Bonded to Silicon Surfaces J. Am. Chem. Soc. 1993, 115, 12631-12632
20. Schwertfeger, H.; Machuy, M. M.; Wurtele, C.; Dahl, J. E. P.; Carlson, R. M. K.; Schreiner, P. R. Diamondoid Phosphines-Selective Phosphorylation of Nanodiamonds Adv. Synth. Catal. 2010, 352, 609-615
21. Dubey, M.; Weidner, T.; Gamble, L. J.; Castner, D. G. Structure and Order of Phosphonic Acid-based Self-assembled Monolayers on Si (100) Langmuir 2010, 26, 14747-14754
22. Mani, G.; Johnson, D. M.; Marton, D.; Dougherty, V. L.; Feldman, M. D.; Patel, D.; Ayon, A. A.; Agrawal, C. M. Stability of Self-assembled Monolayers on Titanium and Gold Langmuir 2008, 24, 6774-84
23. Guerrero, G.; Mutin, P. H.; Vioux, A. Anchoring of Phosphonate and Phosphinate Coupling Molecules on Titania Particles Chem. Mater. 2001, 13, 4367-4373
24. Paniagua, S. A.; Hotchkiss, P. J.; Jones, S. C.; Marder, S. R.; Mudalige, A.; Marrikar, F. S.; Pemberton, J. E.; Armstrong, N. R. Phosphonic Acid Modification of Indium-Tin Oxide Electrodes: Combined XPS/UPS/Contact Angle Studies J. Phys. Chem. C 2008, 112, 7809-7817
25. Lim, M. S.; Smiley, K. J.; Gawalt, E. S. Thermally Driven Stability of Octadecylphosphonic Acid Thin Films Grown on SS316L Scanning 2010, 32, 304-11
26. Gawalt, E. S.; Avaltroni, M. J.; Koch, N.; Schwartz, J. Self-Assembly and Bonding of Alkanephosphonic Acids on the Native Oxide Surface of Titanium Langmuir 2001, 17, 5736-5738
27. Milošev, I.; Metikoš-Huković, M.; Petrović, Ž. Influence of Preparation Methods on the Properties of Self-assembled Films of Octadecylphosphonate on Nitinol: XPS and EIS Studies Mater. Sci. Eng., C 2012, 32, 2604-2616
28. Zhang, B.; Kong, T.; Xu, W.; Su, R.; Gao, Y.; Cheng, G. Surface Functionalization of Zinc Oxide by Carboxyalkylphosphonic Acid Self-assembled Monolayers Langmuir 2010, 26, 4514-22
29. Thissen, P.; Valtiner, M.; Grundmeier, G. Stability of Phosphonic Acid Self-assembled Monolayers on Amorphous and Single-crystalline Aluminum Oxide Surfaces in Aqueous Solution Langmuir 2010, 26, 156-64
30. Wang, M.; Hill, I. G. Fluorinated Alkyl Phosphonic Acid SAMs Replace PEDOT: PSS in Polymer Semiconductor Devices Org. Electron. 2011, 13, 498-505
31. Koutsioubas, A. G.; Spiliopoulos, N.; Anastassopoulos, D. L.; Vradis, A. A.; Priftis, G. D. Formation of Alkane-phosphonic Acid Self-assembled Monolayers on Alumina: An in Situ SPR Study Surf. Interface Anal. 2009, 41, 897-903
32. Aissa, A.; Debbabi, M.; Gruselle, M.; Thouvenot, R.; Gredin, P.; Traksmaa, R.; Tonsuaadu, K. Covalent Modification of Calcium Hydroxyapatite Surface by Grafting Phenyl Phosphonate Moieties J. Solid State Chem. 2007, 180, 2273-2278
33. Yuchenko, R. I.; Peresypkina, L. P.; Miroshnichenko, V. V.; Yurchenko, A. G. Phosphorylated Adamantanes. XV. Phosphorylation of Adamantane by Trivalent Phosphorus Acid Chloride in Sulfuric Acid Zh. Obshch. Khim. 1993, 63, 1534-1539
34. Erokhina, E. V.; Shokova, E. A.; Luzikov, Y. N.; Kovalev, V. V. Dichlorophosphorylation of Adamantanols and 1-Adamantylcarbinols in Trifluoroacetic Acid Synthesis 1995, 851-854
35. Fokin, A. A.; Tkachenko, B. A.; Gunchenko, P. A.; Gusev, D. V.; Schreiner, P. R. Functionalized Nanodiamonds Part I. An Experimental Assessment of Diamantane and Computational Predictions for Higher Diamondoids Chem.-Eur. J. 2005, 11, 7091-101
36. 3 (0001) Interfaces Surf. Sci. 2006, 600, 4870-4877
37. Hollahan, J. R.; Carlson, G. L. Hydroxylation of Polymethylsiloxane Surfaces by Oxidizing Plasmas J. Appl. Polym. Sci. 1970, 14, 2499-2508
38. Aissa, A.; Agougui, H.; Debbabi, M. Surface Modification of Calcium Fluoro and Hydroxyapatite by 1-Octylphosphonic Dichloride Appl. Surf. Sci. 2011, 257, 9002-9007
39. Hanson, E. L.; Schwartz, J.; Nickel, B.; Koch, N.; Danisman, M. F. Bonding Self-assembled, Compact Organophosphonate Monolayers to the Native Oxide Surface of Silicon J. Am. Chem. Soc. 2003, 125, 16074-80
40. Raman, A.; Dubey, M.; Gouzman, I.; Gawalt, E. S. Formation of Self-assembled Monolayers of Alkylphosphonic Acid on the Native Oxide Surface of SS316L Langmuir 2006, 22, 6469-72
41. Jensen, J. O. Vibrational Frequencies and Structural Determination of Adamantane Spectrochim. Acta, Part A 2004, 60, 1895-905
42. Chang, H.; Lin, J.; Wu, J.; Chen, K. Infrared Spectroscopy and Vibrational Relaxation of CHx and CDx Stretches on Synthetic Diamond Nanocrystal Surfaces J. Phys. Chem. 1995, 99, 11081-11088
43. Stettner, J.; Frank, P.; Griesser, T.; Trimmel, G.; Schennach, R.; Gilli, E.; Winkler, A. A Study on the Formation and Thermal Stability of 11-MUA SAMs on Au (111)/Mica and on Polycrystalline Gold Foils Langmuir 2009, 25, 1427-33
44. Spori, D. M.; Venkataraman, N. V.; Tosatti, S. G. P.; Durmaz, F.; Spencer, N. D.; Zürcher, S. Influence of Alkyl Chain Length on Phosphate Self-assembled Monolayers Langmuir 2007, 23, 8053-60
45. Flynn, G.; Keller, L.; Miller, M. In Proceedings of the 29th Annual Lunar and Planetary Science Conference, Houston, TX, March 16-20, 1998.
46. Saavedra, H. M.; Barbu, C. M.; Dameron, A. A.; Mullen, T. J.; Crespi, V. H.; Weiss, P. S. 1-Adamantanethiolate Monolayer Displacement Kinetics Follow a Universal Form J. Am. Chem. Soc. 2007, 129, 10741-6
47. Chandekar, A.; Sengupta, S. K.; Whitten, J. E. Thermal Stability of Thiol and Silane Monolayers: A Comparative Study Appl. Surf. Sci. 2010, 256, 2742-2749
48. Vericat, C.; Vela, M. E.; Benitez, G.; Carro, P.; Salvarezza, R. C. Self-assembled Monolayers of Thiols and Dithiols on Gold: New Challenges for a Well-known System Chem. Soc. Rev. 2010, 39, 1805-34
49. Perkins, C. L. Molecular Anchors for Self-Assembled Monolayers on ZnO: A Direct Comparison of the Thiol and Phosphonic Acid Moieties J. Phys. Chem. C 2009, 113, 18276-18286
50. Hudson, R. The Nature of the Chemical Bonding in Organo-phosphorus Compounds Pure Appl. Chem. 1964, 9, 371-86
51. Deki, S.; Béléké, A. B.; Kotani, Y.; Mizuhata, M. Synthesis of Tungsten Oxide Thin Film by Liquid Phase Deposition Mater. Chem. Phys. 2010, 123, 614-619
52. Bent, S. F. Heads or Tails: Which Is More Important in Molecular Self-assembly? ACS Nano 2007, 1, 10-2
53. Ron, H.; Matlis, S.; Rubinstein, I. Self-Assembled Monolayers on Oxidized Metals. 2. Gold Surface Oxidative Pretreatment, Monolayer Properties, and Depression Formation Langmuir 1998, 14, 1116-1121
54. Mullen, T. J.; Dameron, A. A.; Saavedra, H. M.; Williams, M. E.; Weiss, P. S. Dynamics of Solution Displacement in 1-Adamantanethiolate Self-Assembled Monolayers J. Phys. Chem. C 2007, 111, 6740-6746
55. 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, 1103-69
56. Dameron, A. A.; Charles, L. F.; Weiss, P. S. Structures and Displacement of 1-Adamantanethiol Self-assembled Monolayers on Au{111} J. Am. Chem. Soc. 2005, 127, 8697-704
57. Nakamura, T.; Ohana, T.; Hasegawa, M.; Tsugawa, K.; Suzuki, M.; Ishihara, M.; Tanaka, A.; Koga, Y. Chemical Modification of Diamond Surfaces with Fluorine-Containing Functionalities New Diamond Front. Carbon Technol. 2005, 15, 313-324
58. Dameron, A. A. Controlling Molecular Assemblies. Ph.D. Dissertation, Pennsylvania State University, University Park, PA, 2006.
59. Cassie, A. B. D.; Baxter, S. Wettability of Porous Surfaces Trans. Faraday Soc. 1944, 40, 546-551
60. Israelachvili, J. N.; Gee, M. L. Contact Angles on Chemically Heterogeneous Surfaces Langmuir 1989, 5, 288-289