Fundamentals in the design of molecular electronic devices: Long-range charge carrier transport and electronic coupling

Accounts of Chemical Research

Volumn 32, Issue 3, 1999, Pages 201-207

  Fox, Marye Anne ^a  

^a The University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIMERIZATION; ELECTRONICS; MOLECULAR DYNAMICS; MOLECULAR WEIGHT; PHOTOCHEMISTRY; REVIEW;

EID: 0032909927     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar9600953     Document Type: Review

References (60)

1. Watakabe, A.; Kunitake, T. Characterization of p-Conjugated Monolayers of Oligo(phenylene)-vinylene Derivatives by Absorption Spectroscopy and Fluorescence Microscopy. J. Colloid Interface Sci. 1991, 745, 90-98.
2. Hopfield, J. J.; Onuchic, J. N.; Beratan, D. N. A Molecular Shift Register Based on Electron Transfer. Science 1988, 241, 817-819.
3. Crandall, B. C., Lewis, J., Eds. Nanotechnology: Research and Perspectives; MIT Press: Cambridge, MA, 1992.
4. (a) Fendler, J. H. Size-Quantized Semiconductor Particulate Films Generated in situ at Monolayers. Isr. J. Chem 1993, 33, 41-46.
5. (b) Fendler, J. H. Membrane Mimetic Chemistry, Wiley: New York, 1982.
6. Fox, M. A. Polymeric and Supramolecular Arrays for Directional Energy and Electron Transport Over Macroscopic Distances. Acc. Chem. Res. 1992, 25, 569-574.
7. Guillet, J. Polymer Photophysics and Photochemistry, Cambridge University Press: London, 1985.
8. Fox, M. A.; Chanon, M., Eds. Photoinduced Electron Transfer, Elsevier: Amsterdam, 1988; Vois. A - D.
9. (a) Birks, J. B. The Photochemistry of Aromatic Molecules; Wiley: London, 1970.
10. (b) Kuhn, H., Möbius, D., Bücher, H., Eds. Spectroscopy of Monolayer Assemblies; Wiley: New York, 1972.
11. Schrock, R. R. Recent Advances in the Chemistry and Applications of High Oxidation State Alkylidene Complexes. Pure Appl. Chem. 1994, 66, 1447-1454.
12. Grubbs, R. H. The Development of Functional Group Tolerant ROMP Catalysts. J. Macromol Sci. 1994, A31, 1829-1833.
13. For example, see: Fox, H. H.; Wolf, M. O.; O'Dell, R.; Lin, B. L.; Schrock, R. R.; Wrighton, M. S. Living Cyclopolymerization of 1,6-Heptadiyne Derivatives Using Well-Defined Alkylidene Complexes: Polymerization Mechanism, Polymer Structure, and Polymer Properties. J. Am. Chem. Soc. 1994, 116, 2827-2843.
14. Watkins, D. M.; Fox, M. A. Synthesis and Photophysical Characterization of Aryl-Substituted Polynorbornenediol Acetal and Ketal Multiblock Copolymers. Macromolecules 1995, 28, 4939-4950.
15. Watkins, D. M.; Fox, M. A. Photoinduced Charge Separation and Photophysical Dynamics in Polynorbornene Chromophore-Labeled and Quenched s-Labeled Block Copolymers. J. Am. Chem. Soc. 1996, 118, 4344-4353.
16. Fossum, R. D.; Fox, M. A. Intramolecular Complex Formation and Triplet Energy Transfer in Polynorbornenes Incorporating Benzophenone. J. Am. Chem. Soc. 1997, 119, 1197-1207.
17. Watkins, D. M.; Fox, M. A. Rigid, Well-Defined Block Copolymers for Efficient Light Harvesting. J. Am. Chem. Soc. 1994, 116, 6441-6442.
18. Hong, B.; Fox, M. A. Arene-functionalized Polyisocyanides: Photophysics of Well-Defined Homopolymers and Block Copolymers for Efficient Light Harvesting. Can. J. Chem. 1995, 73, 2101-2110.
19. Fox, H. H.; Fox, M. A. Fluorescence and Singlet Energy Migration in Conformationally Restrained Acrylate Polymers Bearing Pendant Chromophores. Macromolecules 1995, 28, 4570-4576.
20. II Dimetallic Complexes (M = Ni, Pd, Pt). Inorg. Chem. 1995, 34, 36-41.
21. Fox, M. A.; Chandler, D. A. A Semiconductive Nickel-Phosphine Coordination Polymer. Adv. Mater. 1991, 3, 381-385.
22. For example, see: (a) Percec, V.; Ahn, C. H.; Barboiu, B. Self-Encapsulation, Acceleration and Control in the Radical Polymerization of Monodendritic Monomers via Self-Assembly. J. Am. Chem. Soc. 1997, 119, 12978-12979.
23. (b) Percec, V.; Barboiu, B.; Kim, H. J. Arenesulfonyl Halides: A Universal Class of Functional Initiators for Metal-Catalyzed "Living" Radical Polymerization of Styrene(s), Methacrylates, and Acrylates. Ibid. 1998, 120, 305-316.
24. For example, see Jordan, R.; Ulman, A. Surface-Initiated Living Cationic Polymerization of 2-Oxazolines. J. Am. Chem. Soc. 1998, 120, 243-247.
25. Webster, O. W.; Hertler, W. R.; Sogah, D. Y.; Farnham, W. B.; RajanBabu, T. V. Group Transfer Polymerization. 1. A New Concept for Addition Polymerization with Organosilicon Initiators. J. Am. Chem. Soc 1983, 105, 5706-5708.
26. Fox, M. A.; Thompson, H. K. Synthesis and Photophysical Characterization of Group Transfer Polymers with Pendent Aryl Chromophores. Macromolecules 1997, 30, 7391-7396.
27. Ulman, A. An Introduction to Ultrathin Organic Films; Academic Press: Boston, 1991.
28. Porter, M. D.; Bright, T. B.; Allara, D. L.; Chidsey, C. E. D. Spontaneously Organized Molecular Assemblies. 4. Structural Characterization of n-Alkyl Thiol Monolayers on Gold by Optical Ellipsometry, Infrared Spectroscopy, and Electrochemistry. J. Am. Chem. Soc. 1987, 109, 3559-3568.
29. Lee, T. R.; Carey, R. I.; Biebuyck, H. A.; Whitesides, G. M. The Wetting of Monolayer Films Exposing Ionizable Acis and Bases. Langmuir 1994, 10, 741-749.
30. (a) Reese, S.; Fox, M. A. Self-Assembled Monolayers on Gold of Thiols Incorporating Conjugated Terminal Groups. J. Phys. Chem. 1998, submitted.
31. (b) Collard, D. M.; Fox, M. A. The Use of Electroactive Thiols to Study the Formation and Exchange of Alkanethiol Monolayers on Gold. Langmuir 1991, 7, 1192-1197.
32. Wolf, M. O.; Fox, M. A. Photochemistry and Surface Properties of Self-Assembled Monolayers of cis-and trans-4-Cyano-4′-(10-thiodecoxyl)stilbene on Polycrystalline Gold. J. Am. Chem. Soc. 1995, 117, 1845-1846.
33. Whitmore, P. M.; Robota, H. J.; Harris, C. B. Mechanisms for Electronic Energy Transfer Between Molecules and Metal Surfaces: A Comparison of Silver and Nickel. J. Chem. Phys. 1982, 77, 1560-1568.
34. Fox, M. A.; Whitesell, J. K.; McKerrow, A. J. Fluorescence and Redox Activity of Probes Anchored through an Aminotrithiol to Polycrystalline Gold. Langmuir 1998, 14, 816-820.
35. Zhou, X. L.; Zhu, X. Y.; White, J. M. Photodissociation of Intra-adsorbate Bonds at Adsorbate - metal Interfaces. Acc. Chem. Res. 1990, 23, 327-332.
36. Wolf, M. O.; Fox, M. A. Photoisomerization and Photodimerization in Self-Assembled Monolayers of cis-and trans-4-Cyano-4′-(10-mercaptodecoxy)-stilbene on Gold. Langmuir 1996, 12, 955-962.
37. Li, W.; Lynch, V.; Thompson, H.; Fox, M. A. Self-Assembled Monolayers of 7-(10-Thiodecoxy)-coumarin on Gold: Synthesis, Characterization, and Photodimerization. J. Am. Chem. Soc. 1997, 119, 7211-7217.
38. Fox, M. A.; Wooton, M. D. Characterization, Adsorption, and Photochemistry of Self-Assembled Monolayers of 10-Thiodecyl-2-Anthryl ether on Gold. Langmuir, in press.
39. Norrod, L.; Rowlen, K. L. Ozone-Induced Oxidation of Self-Assembled Decanethiol: Contributing Mechanism for Photooxidation? J. Am. Chem. Soc. 1998, 120, 2656-2657.
40. Zhang, Y.; Terrill, R. H.; Tanzer, T. A.; Bohn, P. W. Ozonolysis Is the Primary Cause of UV Photooxidation of Alkanethiolate Monolayers at Low Irradiance. J. Am. Chem. Soc. 1998, 120, 2654-2655.
41. Gust, D.; Moore, T. A.; Moore, A. L. Molecular Mimicry of Photosynthetic Energy and Electron Transfer. Acc. Chem. Res. 1993, 26, 198-205.
42. Gregg, B. A.; Fox, M. A.; Bard, A. J. Photovoltaic Effects in Symmetrical Cells of a Liquid Crystal Porphyrin. J. Phys. Chem. 1990, 94, 1586-1598.
43. Liu, C. Y.; Pan, H. L.; Fox, M. A.; Bard, A. J. High-Density Nanosecond Charge Trapping in Thin Films at the Photoconductor ZnODEP. Science 1993, 261, 897-899.
44. Liu, C. Y.; Pan, H. L.; Fox, M. A.; Bard, A. J. Reversible Charge Trapping/Detrapping in a Photoconductive Insulator of Liquid Crystal Zinc Porphyrin. Chem. Mater. 1997, 9, 1422-1429.
45. Gregg, B. A.; Fox, M. A.; Bard, A. J. 2,3,7,8,12,13,17,18-Octakis(b-hydroxyethyl)-porphyrin and Its Liquid Crystalline Derivatives: Synthesis and Characterization. J. Am. Chem. Soc. 1989, 111, 3024-3029.
46. Gregg, B. A.; Fox, M. A.; Bard, A. J. Effects of Order on the Photophysical Properties of the Liquid Crystal Zinc Octakis (b-octoxyethyl) porphyrin. J. Phys. Chem. 1989, 93, 4227-4234.
47. Fox, M. A.; Grant, J. V.; Melamed, D.; Torimoto, T.; Liu, C. Y.; Bard, A. J. The Effect of Structural Variation on Photocurrent Efficiency in Alkyl-substituted Porphyrin Solid State Thin Layer Photocells. Chem. Mater. 1998, 10, 1771-1776.
48. (a) Warman, J. M.; de Haas, P. E.; Pan, H. L.; Fox, M. A. Charge Migration in Supramolecular Stacks of Porphyrins and Phthalocyanines. Mol. Cryst. Liq. Cryst. 1993, 235, 115-120.
49. (b) Schouten, P. G.; Warman, J. M.; Fox, M. A.; Pan, H. L. Charge Migration in Columnar Aggregates of Peripherally Substituted Porphyrins. Nature 1991, 353, 736.
50. Katz, H. E. Organic Molecular Solids as Thin Film Transistor Semiconductors. J. Mater. Chem. 1997, 7, 369-376.
51. Garnier, F.; Hajlaoui, R.; Yassar, A.; Srivastava, P. All-Polymer Field-Effect Transistor Realized by Printing Techniques. Science 1994, 265, 1684.
52. Hol, W. G. J. The Role of the a-Helix Dipole in Protein Function and Structure. Prog. Biophys. Mol. Biol. 1985, 45, 149-195.
53. Wang, Z.; Pearlstein, R. M.; Jia, Y.; Fleming, G. R.; Norris, J. R. Inhomogeneous Electron-Transfer Kinetics in Reaction Centers of Bacterial Photosynthesis. Chem. Phys. 1993, 176, 421.
54. Boxer, S. G.; Lockhart, D. J.; Franzen, S. Electric Field Effects on Electron-Transfer Reactions in Isotropic Systems. In Photochemical Energy Conversion; Norris, J. R., Meisel, D., Eds.; Elsevier: Amsterdam, 1989; p 196.
55. Galoppini, E.; Fox, M. A. Effect of the Electric Field Generated by the Helix Dipole on Photoinduced Intramolecular Electron Transfer in Dichromophoric a-Helical Peptides. J. Am. Chem. Soc. 1996, 118, 2299-2300.
56. Knorr, A.; Galoppini, E.; Fox, M. A. Photoinduced Intramolecular Electron Transfer in Dichromophoreappended α-Helical Peptides: Spectroscopic Properties and Preferred Conformations. J. Phys. Org. Chem. 1997, 10, 484-498.
57. Batchelder, T. L.; Fox, R. J., III; Meier, M. S.; Fox, M. A. Intramolecular Excited-State Electronic Coupling Along a-Helical Peptide. J. Org Chem. 1996, 61, 4206-4209.
58. Fox, M. A.; Galoppini, E. Electric Fields Effects on Electron-Transfer Rates in Dichromophoric Peptides: The Effect of Helix Unfolding. J. Am. Chem. Soc. 1997, 119, 5277-5285.
59. Hall, D. B.; Barton, J. K. Sensitivity of DNA-Mediated Electron Transfer to the Intervening p-Stack: A Probe for the Integrity of the DNA Base Stack. J. Am. Chem. Soc. 1997, 119, 5045-5046 and references therein.
60. Lewis, F. D.; Wu, T.; Zhang, Y.; Letsinger, R. L.; Greenfield, S. R.; Wasilewski, M. Distance-Dependent Electron Transfer in DNA Hairpins. Science 1997, 277, 673-676.