Hopping Transport in Long Conjugated Molecular Wires Connected to Metals

Charge and Exciton Transport through Molecular Wires

Volumn , Issue , 2011, Pages 61-91

  Choi, Seong H ^a   Daniel Frisbie, C ^a  

^a University of Minnesota   (United States)

Author keywords

Field emission; Hopping; Length dependent transport; Molecular electronics; Molecular junction; Molecular wires; Self assembled monolayer; Tunneling

Indexed keywords

EID: 84885555849     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527633074.ch3     Document Type: Chapter

References (122)

1. Nitzan, A. and Ratner, M.A. (2003) Electron transport in molecular wire junctions. Science, 300, 1384-1389.
2. Davis, W.B., Svec, W.A., Ratner, M.A. and Wasielewski, M.R. (1998) Molecular-wire behaviour in p-phenylenevinylene oligomers. Nature, 396, 60-63.
3. Schwab, P.F.H., Levin, M.D. andMichl, J. (1999) Molecular rods. 1. Simple axial rods. Chem. Rev., 99, 1863-1934.
4. Joachim, C., Gimzewski, J.K. and Aviram, A. (2000) Electronics using hybrid-molecular and mono-molecular devices. Nature, 408, 541-548.
5. Carroll, R.L. and Gorman, C.B. (2002) The genesis of molecular electronics. Angew. Chem. Int. Ed., 41, 4378-4400.
6. Heath, J.R. and Ratner, M.A. (2003) Molecular electronics. Phys. Today, 56, 43-49.
7. Kwok, K.S. and Ellenbogen, J.C. (2002) Moletronics: future electronics. Mater. Today, 5, 28-37.
8. Chen, Y. et al. (2003) Nanoscale molecular-switch crossbar circuits. Nanotechnology, 14, 462-468.
9. Li, G. et al. (2005) High-efficiency solution processable polymer photovoltaic cells by self-organization of polymer blends. Nat. Mater., 4, 864-868.
10. Peet, J. et al. (2007) Efficiency enhancement in low-bandgap polymer solar cells by processing with alkane dithiols. Nat. Mater., 6, 497-500.
11. Sirringhaus, H., Tessler, N. and Friend, R.H. (1998) Integrated optoelectronic devices based on conjugated polymers. Science, 280, 1741-1744.
12. Shen, Z. et al. (1997) Three-color, tunable, organic light-emitting devices. Science, 276, 2009-2011.
13. Greenham, N.C. et al. (1993) Efficient light-emitting diodes based on polymers with high electron affinities. Nature, 365, 628-630.
14. Yan, H. et al. (2009) A high-mobility electron-transporting polymer for printed transistors. Nature, 457, 679-686.
15. Cho, J.H. et al. (2008) Printable ion-gel gate dielectrics for low-voltage polymer thin-film transistors on plastic. Nat. Mater., 7, 900-906.
16. Ruitenbeek, J. et al. (2005) in Introducing Molecular Electronics, Part II Experiment (eds G. Cuniberti, G. Fagas, and K. Richter), Springer, Heidelberg, Germany.
17. Salomon, A. et al. (2003) Comparison of electronic transport measurements on organic molecules. Adv. Mater., 15, 1881-1890.
18. Mantooth, B.A. and Weiss, P.S. (2003) Fabrication, assembly, and characterization of molecular electronics components. Proc. IEEE, 91, 1785-1802.
19. Wang, W.Y., Lee, T.H. and Reed, M.A. (2005) Electronic transport in molecular self-assembled monolayer devices. Proc. IEEE, 93, 1815-1824.
20. Chen, F. et al. (2007) Measurement of single-molecule conductance. Annu. Rev. Phys. Chem., 58, 535-564.
21. Selzer, Y. and Allara, D.L. (2006) Single-molecule electrical junctions. Annu. Rev. Phys. Chem., 57, 593-623.
22. McCreery, R.L. (2004) Molecular electronic junctions. Chem. Mater., 16, 4477-4496.
23. Venkataraman, L. et al. (2006) Dependence of single-molecule junction conductance on molecular conformation. Nature, 442, 904-907.
24. Wold, D.J., Haag, R., Rampi, M.A. and Frisbie, C.D. (2002) Distance dependence of electron tunneling through self-assembled monolayers measured by conducting probe atomic force microscopy: unsaturated versus saturated molecular junctions. J. Phys. Chem. B, 106, 2813-2816.
25. Liu, H. et al. (2008) Length-dependent conductance of molecular wires and contact resistance in metal-molecule-metal junctions. ChemPhysChem, 9, 1416-1424.
26. Kim, B.-S. et al. (2006) Correlation between HOMO alignment and contact resistance in molecular junctions: aromatic thiols versus aromatic isocyanides. J. Am. Chem. Soc., 128, 4970-4971.
27. Engelkes, V.B., Beebe, J.M. and Frisbie, C.D. (2004) 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., 126, 14287-14296.
28. Lakshmi, S., Dutta, S. and Pati, S.K. (2008) Molecular electronics: effect of external electric field. J. Phys. Chem. C, 112, 14718-14730.
29. Wang, W., Lee, T. and Reed, M.A. (2003) Mechanism of electron conduction in self-assembled alkanethiol monolayer devices. Phys. Rev. B, 68, 035416.
30. Selzer, Y., Cabassi, M.A., Mayer, T.S. and Allara, D.L. (2004) Thermally activated conduction in molecular junctions. J. Am. Chem. Soc., 126, 4052-4053.
31. Poot, M. et al. (2006) Temperature dependence of three-terminal molecular junctions with sulfur end-functionalized tercyclohexylidenes. Nano Lett., 6, 1031-1035.
32. Li, X. et al. (2007) Thermally activated electron transport in single redox molecules. J. Am. Chem. Soc., 129, 11535-11542.
33. Choi, S.H., Kim, B.-S. and Frisbie, C.D. (2008) Electrical resistance of long conjugated molecular wires. Science, 320, 1482-1486.
34. Mayor, M. et al. (2003) Electric current through a molecular rod? Relevance of the position of the anchor groups. Angew. Chem. Int. Ed., 42, 5834-5838.
35. Haiss, W. et al. (2006) Thermal gating of the single molecule conductance of alkanedithiols. Faraday Discuss., 131, 253-264.
36. Selzer, Y. et al. (2005) Effect of local environment on molecular conduction: isolated molecule versus self-assembled monolayer. Nano Lett., 5, 61-65.
37. Selzer, Y., Cabassl, M.A., Mayer, T.S. and Allara, D.L. (2004) Temperature effects on conduction through a molecular junction. Nanotechnology, 15, S483-S488.
38. Venkataraman, L. et al. (2006) Single-molecule circuits with well-defined molecular conductance. Nano Lett., 6, 458-462.
39. Venkataraman, L. et al. (2007) Electronics and chemistry: varying single-molecule junction conductance using chemical substituents. Nano Lett., 7, 502-506.
40. Chen, F. et al. (2006) Effect of anchoring groups on single-molecule conductance: comparative study of thiol-, amine-, and carboxylic-acid-terminated molecules. J. Am. Chem. Soc., 128, 15874-15881.
41. Xu, B. and Tao, N.J. (2003) Measurement of single-molecule resistance by repeated formation of molecular junction. Science, 301, 1221-1223.
42. Yasuda, S. et al. (2006) Bond fluctuation of S/Se anchoring observed in single-molecule conductance measurements using the point contact method with scanning tunneling microscopy. J. Am. Chem. Soc., 128, 7746-7747.
43. Anslyn, E.V. and Dougherty, D.A.(2006) Modern Physical Organic Chemistry, Chapter 10, University Science Books, Sausalito.
44. Closs, G.L. and Miller, J.R. (1988) Intramolecular long-distance electron transfer in organic molecules. Science, 240, 440-447.
45. Jordan, K.D. and Paddon-Row, M.N. (1992) Analysis of the interactions responsible for long-range through-bond-mediated electronic coupling between remote chromophores attached to rigid polynorbornyl bridges. Chem. Rev., 92, 395-410.
46. Marcus, R.A. (1993) Electron transfer reactions in chemistry: theory and experiment (nobel lecture). Angew. Chem. Int. Ed., 32, 1111-1222.
47. Barbara, P.F., Meyer, T.J. and Ratner, M.A. (1996) Contemporary issues in electron transfer research. J. Phys. Chem., 100, 13148-13168.
48. Weiss, E.A. et al. (2005) Conformationally gated switching between superexchange and hopping within oligo-p-phenylene-based molecular wires. J. Am. Chem. Soc., 127, 11842-11850.
49. Newton, M.D. (1991) Quantum chemical probes of electron-transfer kinetics: the nature of donor-acceptor interactions. Chem. Rev., 91, 767-792.
50. Lambert, C., Noll, G. and Schelter, J. (2002) Bridge-mediated hopping or superexchange electron-transfer processes in bis(triarylamine) systems. Nat. Mater., 1, 69-73.
51. Berlin, Y.A. et al. (2003) Charge hopping in molecular wires as a sequence of electron-transfer reactions. J. Phys. Chem. A, 107, 3970-3980.
52. Sachs, S.B. et al. (1997) Rates of interfacial electron transfer through p-conjugated spacers. J. Am. Chem. Soc., 119, 10563-10564.
53. Curtiss, L.A., Naleway, C.A. and Miller, J.R. (1995) Superexchange pathway calculation of electronic coupling through cyclohexane spacers. J. Phys. Chem., 99, 1182-1193.
54. Paulson, B. et al. (1993) Long-distance electron transfer through rodlike molecules with cubyl spacers. J. Phys. Chem., 97, 13042-13045.
55. Berlin, Y.A., Grozema, F.C., Siebbeles, L.D.A. and Ratner, M.A. (2008) Charge transfer in donor-bridge-acceptor systems: static disorder, dynamic fluctuations, and complex kinetics. J. Phys. Chem. C, 112, 10988-11000.
56. Nitzan, A. (2001) A relationship between electron-transfer rates and molecular conduction. J. Phys. Chem. A, 105, 2677-2679.
57. Adams, D.M. et al. (2003) Charge transfer on the nanoscale: current status. J. Phys. Chem. B, 107, 6668-6697.
58. Zhu, X.-Y. (2004) Charge transport at metal-molecule interfaces: a spectroscopic view. J. Phys. Chem. B, 108, 8778-8793.
59. Zhu, X.Y. (2004) Electronic structure and electron dynamics at molecule-metal interfaces: implications for molecule-based electronics. Surf. Sci. Rep., 56, 1-83.
60. Park, H. et al. (2000) Nanomechanical oscillations in a single-C60 transistor. Nature, 407, 57-60.
61. Park, J. et al. (2002) Coulomb blockade and the Kondo effect in single-atom transistors. Nature, 417, 722-725.
62. Chae, D.-H. et al. (2006) Vibrational excitations in single trimetal-molecule transistors. Nano Lett., 6, 165-168.
63. Ashcroft, N.W. and Mermin, N.D. (1976) Solid State Physics, Chapter 1, Holt Rinehart & Winston, Austin.
64. Wiesendanger, R. (1994) Scanning Probe Microscopy, Cambridge University Press, Cambridge.
65. Simmons, J.G. (1963) Generalized formula for the electric tunnel effect between similar electrodes separated by a thin insulating film. J. Appl. Phys., 34, 1793-1803.
66. Landauer, R. (1981) Can a length of perfect conductor have a resistance? Phys. Lett. A, 85, 91-93.
67. Datta, S. (2004) Electrical resistance: an atomistic view. Nanotechnology, 15, S433-S451.
68. Nitzan, A. (2001) Electron transmission through molecules and molecular interfaces. Annu. Rev. Phys. Chem., 52, 681-750.
69. Joachim, C. and Ratner, M.A. (2005) Molecular electronics: some views on transport junctions and beyond. Proc. Natl. Acad. Sci. USA, 102, 8801-8808.
70. Segal, D. et al. (2000) Electron transfer rates in bridged molecular systems 2. A steady-state analysis of coherent tunneling and thermal transitions. J. Phys. Chem. B, 104, 3817-3829.
71. Segal, D., Nitzan, A., Ratner, M. and Davis, W.B. (2000) Activated conduction in microscopic molecular junctions. J. Phys. Chem. B, 104, 2790-2793.
72. Segal, D. and Nitzan, A. (2001) Steady-state quantum mechanics of thermally relaxing systems. Chem. Phys., 268, 315-335.
73. Young, R., Ward, J. and Scire, F. (1971) Observation of metal-vacuum-metal tunneling, field emission, and the transition region. Phys. Rev. Lett., 27, 922-924.
74. Beebe, J.M. et al. (2006) Transition from direct tunneling to field emission in metal-molecule-metal junctions. Phys. Rev. Lett., 97, 026801.
75. Beebe, J.M., Kim, B.-S., Frisbie, C.D. and Kushmerick, J.G. (2008) Measuring relative barrier heights in molecular electronic junctions with transition voltage spectroscopy. ACS Nano, 2, 827-832.
76. Mujica, V., Kemp, M. and Ratner, M.A. (1994) Electron conduction in molecular wires. II. Application to scanning tunneling microscopy. J. Chem. Phys., 101, 6856-6864.
77. Mujica, V., Kemp, M. and Ratner, M.A. (1994) Electron conduction in molecular wires. I. A scattering formalism. J. Chem. Phys., 101, 6849-6855.
78. Beebe, J.M., Engelkes, V.B., Miller, L.L. and Frisbie, C.D. (2002) Contact resistance in metal-molecule-metal junctions based on aliphatic SAMs: effects of surface linker and metal work function. J. Am. Chem. Soc., 124, 11268-11269.
79. Baranovski, S. and Rubel, O. (2006) in Charge Transport in Disordered Solids with Applications in Electronics, Chapter 2 (ed. S. Baranovski), John Wiley & Sons, Ltd, New York, NY.
80. Miller, A. and Abrahams, E. (1960) Impurity conduction at low concentrations. Phys. Rev., 120, 745.
81. Cui, X.D. et al. (2001) Reproducible measurement of single-molecule conductivity. Science, 294, 571-574.
82. Yaliraki, S.N., Kemp, M. and Ratner, M.A. (1999) Conductance of molecular wires: influence of molecule-electrode binding. J. Am. Chem. Soc., 121, 3428-3434.
83. Yaliraki, S.N. and Ratner, M.A. (1998) Molecule-interface coupling effects on electronic transport in molecular wires. J. Chem. Phys., 109, 5036-5043.
84. Datta, S. (1995) Electronic Transport in Mesoscopic Systems, Cambridge University Press, New York, NY.
85. Gadzuk, J.W. and Plummer, E.W. (1971) Field emission energy distribution (FEED). Rev. Mod. Phys., 45, 487-548.
86. Meisel, K.D., Vocks, H. and Bobbert, P.A. (2005) Polarons in semiconducting polymers: study within an extended holstein model. Phys. Rev. B, 71, 205206.
87. Segal, D. and Nitzan, A. (2002) Conduction in molecular junctions: inelastic effects. Chem. Phys., 281, 235-256.
88. Zade, S.S. and Bendikov, M. (2008) Study of hopping transport in long oligothiophenes and oligoselenophenes: dependence of reorganization energy on chain length. Chem. Eur. J., 14, 6734-6741.
89. Efros, A.L. and Shklovskii, B.I. (1975) Coulomb gap and low temperature conductivity of disordered systems. J. Phys. C: Solid State Phys., 8, L49-L51.
90. Rose, A. (1955) Space-charge-limited currents in solids. Phys. Rev., 97, 1538.
91. Lampert, M.A. (1956) Simplified theory of space-charge-limited currents in an insulator with traps. Phys. Rev., 103, 1648.
92. Tuccitto, N. et al. (2009) Highly conductive ̃-nm-long molecular wires assembled by stepwise incorporation of metal centres. Nat. Mater., 8, 41-46.
93. Holmlin, R.E. et al. (2001) Electron transport through thin organic films in metal-insulator-metal junctions based on self-assembled monolayers. J. Am. Chem. Soc., 123, 5075-5085.
94. Lafferentz, L. et al. (2009) Conductance of a single conjugated polymer as a continuous function of its length. Science, 323, 1193-1197.
95. Rosink, J.J.W.M. et al. (2000) Self-assembly of π-conjugated azomethine oligomers by sequential deposition of monomers from solution. Langmuir, 16, 4547-4553.
96. Kelley, T.W., Granstrom, E. and Frisbie, C.D. (1999) Conducting probe atomic force microscopy: a characterization tool for molecular electronics. Adv. Mater., 11, 261-264.
97. Wold, D.J. and Frisbie, C.D. (2000) Formation of metal-molecule-metal tunnel junctions: microcontacts to alkanethiol monolayers with a conducting AFM tip. J. Am. Chem. Soc., 122, 2970-2971.
98. Wold, D.J. and Frisbie, C.D. (2001) Fabrication and characterization of metal-molecule-metal junctions by conducting probe atomic force microscopy. J. Am. Chem. Soc., 123, 5549-5556.
99. Leatherman, G. et al. (1999) Carotene as a molecular wire: conducting atomic force microscopy. J. Phys. Chem. B, 103, 4006-4010.
100. Engelkes, V.B. and Frisbie, C.D. (2006) Simultaneous nanoindentation and electron tunneling through alkanethiol self-assembled monolayers. J. Phys. Chem. B, 110, 10011-10020.
101. Engelkes, V.B., Beebe, J.M. and Frisbie, C.D. (2005) Analysis of the causes of variance in resistance measurements on metal-molecule-metal junctions formed by conducting-probe atomic force microscopy. J. Phys. Chem. B, 109, 16801-16810.
102. Giese, B. (2000) Long-distance charge transport in DNA: the hopping mechanism. Acc. Chem. Res., 33, 631-636.
103. Giese, B. et al. (2001) Direct observation of hole transfer through DNA by hopping between adenine bases and by tunnelling. Nature, 412, 318-320.
104. Conwell, E.M. (2005) Charge transport in DNA in solution: the role of polarons. Proc. Natl. Acad. Sci. USA, 102, 8795-8799.
105. Shen, Y., Hosseini, A.R., Wong, M.H. and Malliaras, G.G. (2004) How to make ohmic contacts to organic semiconductors. ChemPhysChem, 5, 16-25.
106. Akaba, R., Tokumaru, K. and Kobayashi, T. (1980) Electronic structure and conformations of N-benzylideneanilines. I. Electronic absorption spectral study combined with CNDO/S CI calculations. Bull. Chem. Soc. Jpn., 53, 1993-2001.
107. Tsuji, T., Takeuchi, H., Egawa, T. and Konaka, S. (2001) Effects of molecular structure on the stability of a thermotropic liquid crystal. Gas electron diffraction study of the molecular structure of phenyl benzoate. J. Am. Chem. Soc., 123, 6381-6387.
108. Harada, J., Harakawa, M. and Ogawa, K. (2004) Torsional vibration and central bond length of N-benzylideneanilines. Acta Crystallogr. B, 60, 578-588.
109. Yu, W. et al. (2006) Crystal structure and geometry-optimization study of 4-methyl-3',5'-dinitro-4'-methyl benzylidene aniline. J. Mol. Struct., 794, 255-260.
110. Kubatkin, S. et al. (2003) Single-electron transistor of a single organic molecule with access to several redox states. Nature, 425, 698-701.
111. Sze, S.M. (1981) Physics of Semiconductor Devices, 2nd edn, Chapter 7, John Wiley & Sons, Inc., New York, NY.
112. Morgan, P.W., Kwolek, S.L. and Pletcher, T.C. (1987) Aromatic azomethine polymers and fibers. Macromolecules, 20, 729-739.
113. Yang, C.-J. and Jenekhe, S.A. (1995) Group contribution to molar refraction and refractive index of conjugated polymers. Chem. Mater., 7, 1276-1285.
114. Liu, C.-L. and Chen, W.-C. (2005) Fluorene-based conjugated poly(azomethine)s: synthesis, photophysical properties, and theoretical electronic structures. Macromol. Chem. Phys., 206, 2212-2222.
115. Tsai, F.-C. et al. (2005) New thiophene-linked conjugated poly(azomethine)s: theoretical electronic structure, synthesis, and properties. Macromolecules, 38, 1958-1966.
116. Berkesi, O. et al. (2003) Hydrogen bonding interactions of benzylidene type schiff bases studied by vibrational spectroscopic and computational methods. Phys. Chem. Chem. Phys., 5, 2009-2014.
117. Krebs, F.C. and Jorgensen, M. (2002) Controlling the energy levels of conducting polymers. Hydrogen versus fluorine in poly(dialkylterphenylenevinylene)s. Macromolecules, 35, 7200-7206.
118. Anthony, J.E. (2006) Functionalized acenes and heteroacenes for organic electronics. Chem. Rev., 106, 5028-5048.
119. Yoon, M.-H., Facchetti, A., Stern, C.E. and Marks, T.J. (2006) Fluorocarbon-modified organic semiconductors: molecular architecture, electronic, and crystal structure tuning of arene-versus fluoroarene-thiophene oligomer thin-film properties. J. Am. Chem. Soc., 128, 5792-5801.
120. Renak, M.L. et al. (1999) Fluorinated distyrylbenzene chromophores: effect of fluorine regiochemistry on molecular properties and solid-state organization. J. Am. Chem. Soc., 121, 7787-7799.
121. Beaujuge, P.M., Ellinger, S. and Reynolds, J.R. (2008) The donor-acceptor approach allows a black-to-transmissive switching polymeric electrochrome. Nat. Mater., 7, 795-799.
122. Yang, C. et al. (2008) Visible-near infrared absorbing dithienylcyclopentadienone-thiophene copolymers for organic thin-film transistors. J. Am. Chem. Soc., 130, 16524-16526.