Tuning the Work Function of Gold with Self-Assembled Monolayers Derived from X-[C6H4-C≡C-]nC6H 4-SH (n = 0, 1, 2; X = H, F, CH3, CF3, and OCH3)

Langmuir

Volumn 15, Issue 4, 1999, Pages 1121-1127

  Zehner, Robert W ^a   Parsons, Bradley F ^a   Hsung, Richard P ^a,b   Sita, Lawrence R ^a,c  

^a UNIVERSITY OF CHICAGO   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c Bldg 142   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMISORPTION; MOLECULAR STRUCTURE; MONOLAYERS; SULFUR COMPOUNDS;

KELVIN PROBE METHOD; SELF ASSEMBLED MONOLAYERS (SAM);

GOLD;

EID: 0033077973     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la981114f     Document Type: Article

References (41)

1. Jackson, N.; Lin, Y. Y.; Gundlach, D. J.; Klauk, H. IEEE J. Sel. Top. Quantum Electron. 1998, 4, 100-104.
2. Dodabalapur, A. Solid State Commun. 1997, 102, 259-267.
3. Arai, M.; Nakaya, K.; Onitsuka, O.; Inoue, T.; Codama, M.; Tanaka, M.; Tanabe, H. Synth. Met. 1997, 91, 21-25.
4. Sheats, J. R. Science 1997, 277, 191-192.
5. Lo, R. K.; Ritchie, J. E.; Zhou, J. P.; Zhao, J. N.; McDevitt, J. T.; Xu, F.; Mirkin, C. A. J. Am. Chem. Soc. 1996, 118, 11295-11296.
6. Evans, S. D.; Ulman, A. Chem. Phys. Lett. 1990, 170, 462-466.
7. Bruening, M.; Moons, E.; Yaron-Marcovich, D.; Cahen, D.; Libman, J.; Shanzer, A. J. Am. Chem. Soc. 1994, 116, 2972-2977.
8. Bruening, M.; Moons, E.; Cahen, D.; Shanzer, A. J. Phys. Chem. 1995, 99, 8368-8373.
9. Campbell, I. H.; Rubin, S.; Zawodinski, T. A.; Kress, J. D.; Martin, R. L.; Smith, D. L.; Barashkov, N. N.; Ferraris, J. P. Phys. Rev. B 1996, 54, 14321-14324.
10. Ulman, A. An introduction to ultrathin organic films: from Langmuir - Blodgett to self-assembly, 1st ed.; Academic Press: San Diego, CA, 1991.
11. Dhirani, A.-A.; Zehner, R. W.; Hsung, R. P.; Guyot-Sionnest, P.; Sita, L. R. J. Am. Chem. Soc. 1996, 118, 3319-3320.
12. Dhirani, A.-A.; Lin, P.-H.; Guyot-Sionnest, P.; Zehner, R. W.; Sita, L. R. J. Chem. Phys. 1996, 106, 5249-5253.
13. Zehner, R. W.; Sita, L. R. Langmuir 1997, 13, 2973-2979.
14. Cygan, M. T.; Dunbar, T. D.; Arnold, J. J.; Bumm, L. A.; Shedlock, N. F.; Burgin, T. P.; Jones, L., II; Allara, D. L.; Tour, J. M.; Weiss, P. S. J. Am. Chem. Soc. 1998, 120, 2721-2732.
15. Bumm, L. A.; Arnold, J. J.; Cygan, M. T.; Dunbar, T. D.; Burgin, T. P.; Jones, L., II; Allara, D. L.; Tour, J. M.; Weiss, P. S. Science 1996, 271, 1705-1707.
16. Tour, J. M.; Jones, L.; Pearson, D. L.; Lamba, J. J. S.; Burgin, T. P.; Whitesides, G. M.; Allara, D. L.; Parikh, A. N.; Atre, S. V. J. Am. Chem. Soc. 1995, 117, 9529-9534.
17. Samori, P; Francke, V.; Mangel, T.; Mullen, K.; Rabe, J. R Opt. Mater. 1998, 9, 390-393.
18. Francke, V.; Mangel, T.; Mullen, K. Macromolecules 1998, 31, 2447-2453.
19. Campbell, I. H.; Kress, J. D.; Martin, R. L.; Smith, D. L. Appl. Phys. Lett. 1997, 71, 3528-3530.
20. Sachs, S. B.; Dudek, S. B.; Hsung, R. P.; Sita, L. R.; Smalley, J. F.; Newton, M. D.; Feldberg, S. W.; Chidsey, C. E. D. J. Am. Chem. Soc. 1997, 119, 10563-10564.
21. For recent studies of the electronic properties of SAMs derived from paraphenylene oligomers, see: (a) Reed, M. A.; Zhou, C.; Muller, C. J.; Burgin, T. P.; Tour, J. M. Science 1997, 278, 252-254.
22. (b) Tian, W.; Datta, S.; Hong, S.; Reifenberger, R.; Henderson, J. I.; Kubiak, C. P. J. Chem. Phys. 1998, 109, 2874-2882.
23. Jones, L., II; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410.
24. Pearson, D. L.; Tour, J. M. J. Org. Chem. 1997, 62, 1376-1387.
25. (a) Hsung, R. P.; Chidsey, C. E. D.; Sita, L. R. Organometallics 1995, 14, 4808-4815.
26. (b) Hsung, R. P.; Babcock, J. R.; Chidsey, C. E. D.; Sita, L. R. Tetrahedron Lett. 1995, 36, 4525-4528.
27. Additional information provided in the Supporting Information.
28. Guo, L. H.; Facci, J. S.; McLendon, G.; Mosher, R. Langmuir 1994, 10, 4588-4593.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94; E.2 ed.; Gaussian, Inc.: Pittsburgh, PA, 1995.
30. For alternative syntheses of this compound, see: (a) Misumi, S. Bull. Chem. Soc. Jpn. 1961, 34, 1827-1832.
31. (b) Haenninen, E.;Takalo, H.; Kankare, J. Acta Chem. Scand. Ser. B 1988, 42, 614-619.
32. (c) Lavastre, O.; Cabioch, S.; Dixneuf, P. H.; Vohlidal, J. Tetrahedron 1997, 53, 7595-7604.
33. Hoger, S.; Enkelmann, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 2713-2716.
34. Christman, K. Introduction to Surface Physical Chemistry; Baumgärtel, H., Franck, E. U., Grübein, W., Eds.; Springer-Verlag: New York, 1991.
35. McAllister Technical Services. KP6500 Digital Kelvin Probe User's Guide, 3rd ed.; McAllister Technical Services: Coeur d'Alene, ID, 1997.
36. Evans, S. D.; Urankar, E.; Ulman, A.; Ferris, N. J. Am. Chem. Soc. 1991, 113, 4121-4131.
37. Taylor, D. M.; De Oliviera, O. N., Jr.; Morgan, H. J. Colloid Interface Sci. 1990, 139, 508-518.
38. Demchak, R. J.; Fort, T., Jr. J. Colloid Interface Sci. 1974, 46, 191-202.
39. Lowry, T. H.; Richardson, K. S. Mechanism and theory in organic chemistry; 3rd ed.; Harper & Row: New York, 1987.
40. Bastide, S.; Butruille, R.; Cahen, D.; Dutta, A.; Libman, J.; Shanzer, A.; Sun, L.; Vilan, A. J. Phys. Chem. B 1997, 101, 2678-2684.
41. Weast, R. C. Handbook of Chemistry and Physics, 52nd ed.; Chemical Rubber Company: Cleveland, OH, 1971; Vol. 1.