Hopping transport and rectifying behavior in long donor-acceptor molecular wires

Journal of Physical Chemistry C

Volumn 118, Issue 46, 2014, Pages 26485-26497

  Luo, Liang ^a   Balhorn, Luke ^a   Vlaisavljevich, Bess ^a   Ma, Dongxia ^a   Gagliardi, Laura ^a   Frisbie, C Daniel ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATOMIC FORCE MICROSCOPY; DENSITY FUNCTIONAL THEORY; DIODES; ELECTRON TRANSPORT PROPERTIES; ELECTRONIC STRUCTURE; GOLD METALLOGRAPHY; GROUND STATE; NANOWIRES; SUBSTRATES; WIRE;

CONDUCTING PROBE-ATOMIC FORCE MICROSCOPIES; CURRENT RECTIFICATIONS; ELECTRONIC DECOUPLING; ENERGY LEVEL ALIGNMENT; MEASUREMENT TEMPERATURES; RECTIFICATION RATIO; RECTIFYING BEHAVIORS; TRANSPORT MECHANISM;

ELECTRIC RECTIFIERS;

EID: 84914694873     PISSN: 19327447     EISSN: 19327455     Source Type: Journal    
DOI: 10.1021/jp507044n     Document Type: Article

References (82)

1. Aviram, A.; Ratner, M. A. Molecular Rectifiers. Chem. Phys. Lett. 1974, 29, 277-283.
2. Mirkin, C. A.; Ratner, M. A. Molecular Electronics. Annu. Rev. Phys. Chem. 1992, 43, 719-754.
3. Heath, J. R.; Ratner, M. A. Molecular Electronics. Phys. Today 2003, May, 43-49.
4. Joachim, C.; Ratner, M. A. Molecular Electronics: Some Views on Transport Junctions and beyond. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 8801-8808.
5. Fan, F. R. F.; Yang, J. P.; Cai, L. T.; Price, D. W.; Dirk, S. M.; Kosynkin, D. V.; Yao, Y. X.; Rawlett, A. M.; Tour, J. M.; Bard, A. J. Charge Transport through Self-Assembled Monolayers of Compounds of Interest in Molecular Electronics. J. Am. Chem. Soc. 2002, 124, 5550-5560.
6. Nitzan, A.; Ratner, M. A. Electron Transport in Molecular Wire Junctions. Science 2003, 300, 1384-1389.
7. Tao, N. J. Electron Transport in Molecular Junctions. Nat. Nanotechnol. 2006, 1, 173-181.
8. Lindsay, S. M.; Ratner, M. A. Molecular Transport Junctions: Clearing Mists. Adv. Mater. 2007, 19, 23-31.
9. Moth-Poulsen, K.; Bjornholm, T. Molecular Electronics with Single Molecules in Solid-State Devices. Nat. Nanotechnol. 2009, 4, 551-556.
10. McCreery, R. L.; Bergren, A. J. Progress with Molecular Electronic Junctions: Meeting Experimental Challenges in Design and Fabrication. Adv. Mater. 2009, 21, 4303-4322.
11. Scott, G. D.; Natelson, D. Kondo Resonances in Molecular Devices. ACS Nano 2010, 4, 3560-3579.
12. Liang, W. J.; Shores, M. P.; Bockrath, M.; Long, J. R.; Park, H. Kondo Resonance in a Single-Molecule Transistor. Nature 2002, 417, 725-729.
13. Park, J.; Pasupathy, A. N.; Goldsmith, J. I.; Chang, C.; Yaish, Y.; Petta, J. R.; Rinkoski, M.; Sethna, J. P.; Abruna, H. D.; McEuen, P. L.; et al. Coulomb Blockade and the Kondo Effect in Single-Atom Transistors. Nature 2002, 417, 722-725.
14. Kubatkin, S.; Danilov, A.; Hjort, M.; Cornil, J.; Bredas, J.-L.; Stuhr-Hansen, N.; Hedegard, P.; Bjornholm, T. Single-Electron Transistor of a Single Organic Molecule with Access to Several Redox States. Nature 2003, 425, 698-701.
15. Danilov, A.; Kubatkin, S.; Kafanov, S.; Hedegard, P.; Stuhr-Hansen, N.; Moth-Poulsen, K.; Bjornholm, T. Electronic Transport in Single Molecule Junctions: Control of the Molecule-Electrode Coupling through Intramolecular Tunneling Barriers. Nano Lett. 2008, 8, 1-5.
16. McCreery, R.; Dieringer, J.; Solak, A. O.; Snyder, B.; Nowak, A. M.; McGovern, W. R.; DuVall, S. Molecular Rectification and Conductance Switching in Carbon-Based Molecular Junctions by Structural Rearrangement Accompanying Electron Injection. J. Am. Chem. Soc. 2003, 125, 10748-10758.
17. Blum, A. S.; Kushmerick, J. G.; Long, D. P.; Patterson, C. H.; Yang, J. C.; Henderson, J. C.; Tour, J. M.; Shashidhar, R.; Ratna, B. R. Molecularly Inherent Voltage-Controlled Conductance Switching. Nat. Mater. 2005, 4, 167-172.
18. Weiss, E. A.; Tauber, M. J.; Kelley, R. F.; Ahrens, M. J.; Ratner, M. A.; Wasielewski, M. R. Conformationally Gated Switching between Superexchange and Hopping within Oligo-p-Phenylene-Based Molecular Wires. J. Am. Chem. Soc. 2005, 127, 11842-11850.
19. He, J.; Fu, Q.; Lindsay, S.; Ciszek, J. W.; Tour, J. M. Electrochemical Origin of Voltage-Controlled Molecular Conductance Switching. J. Am. Chem. Soc. 2006, 128, 14828-14835.
20. Lotscher, E.; Ciszek, J. W.; Tour, J.; Riel, H. Reversible and Controllable Switching of a Single-Molecule Junction. Small 2006, 2, 973-977.
21. Ashwell, G. J.; Tyrrell, W. D.; Whittam, A. J. Molecular Rectification: Self-assembled Monolayers in which Donor-(π-bridge)-Acceptor Moieties Are Centrally Located and Symmetrically Coupled to Both Gold Electrodes. J. Am. Chem. Soc. 2004, 126, 7102-7110.
22. Baldwin, J. W.; Amaresh, R. R.; Peterson, I. R.; Shumate, W. J.; Cava, M. P.; Amiri, M. A.; Hamilton, R.; Ashwell, G. J.; Metzger, R. M. Rectification and Nonlinear Optical Properties of A Langmuir-Blodgett Monolayer of a Pyridinium Dye. J. Phys. Chem. B 2002, 106, 12158-12164.
23. Metzger, R. M.; Chen, B.; Hopfner, U.; Lakshmikantham, M. V.; Vuillaume, D.; Kawai, T.; Wu, X. L.; Tachibana, H.; Hughes, T. V.; Sakurai, H.; et al. Unimolecular Electrical Rectification in Hexadecylquinolinium Tricyanoquinodimethanide. J. Am. Chem. Soc. 1997, 119, 10455-10466.
24. Martin, A. S.; Sambles, J. R.; Ashwell, G. J. Molecular Rectifier. Phys. Rev. Lett. 1993, 70, 218-221.
25. Metzger, R. M. Unimolecular Electrical Rectifiers. Chem. Rev. 2003, 103, 3803-3834.
26. Metzger, R. M. Electrical Rectification by A Molecule: The Advent of Unimolecular Electronic Devices. Acc. Chem. Res. 1999, 32, 950-957.
27. Chabinyc, M. L.; Chen, X.; Holmlin, R. E.; Jacobs, H.; Skulason, H.; Frisbie, C. D.; Mujica, V.; Ratner, M. A.; Rampi, M. A.; Whitesides, G. M. Molecular Rectification in a Metal-Insulator-Metal Junction Based on Self-Assembled Monolayers. J. Am. Chem. Soc. 2002, 124, 11730-11736.
28. Nijhuis, C. A.; Reus, W. F.; Whitesides, G. M. Molecular Rectification in Metal-SAM-Metal Oxide-Metal Junctions. J. Am. Chem. Soc. 2009, 131, 17814-17827.
29. Nijhuis, C. A.; Reus, W. F.; Barber, J. R.; Dickey, M. D.; Whitesides, G. M. Charge Transport and Rectification in Arrays of SAM-Based Tunneling Junctions. Nano Lett. 2010, 10, 3611-3619.
30. Nijhuis, C. A.; Reus, W. F.; Whitesides, G. M. Mechanism of Rectification in Tunneling Junctions Based on Molecules with Asymmetric Potential Drops. J. Am. Chem. Soc. 2010, 132, 18386-18401.
31. Wimbush, K. S.; Reus, W. F.; van der Wiel, W. G.; Reinhoudt, D. N.; Whitesides, G. M.; Nijhuis, C. A.; Velders, A. H. Control over Rectification in Supramolecular Tunneling Junctions. Angew. Chem., Int. Ed. 2010, 49, 10176-10180.
32. Ng, M. K.; Lee, D. C.; Yu, L. P. Molecular Diodes Based on Conjugated Diblock Co-oligomers. J. Am. Chem. Soc. 2002, 124, 11862-11863.
33. Ng, M. K.; Yu, L. P. Synthesis of Amphiphilic Conjugated Diblock Oligomers as Molecular Diodes. Angew. Chem., Int. Ed. 2002, 41, 3598-3601.
34. Jiang, P.; Morales, G. M.; You, W.; Yu, L. P. Synthesis of Diode Molecules and Their Sequential Assembly to Control Electron Transport. Angew. Chem., Int. Ed. 2004, 43, 4471-4475.
35. Diez-Perez, I.; Hihath, J.; Lee, Y.; Yu, L. P.; Adamska, L.; Kozhushner, M. A.; Oleynik, I. I.; Tao, N. J. Rectification and Stability of A Single Molecular Diode with Controlled Orientation. Nat. Chem. 2009, 1, 635-641.
36. Elbing, M.; Ochs, R.; Koentopp, M.; Fischer, M.; von Hanisch, C.; Weigend, F.; Evers, F.; Weber, H. B.; Mayor, M. A Single-Molecule Diode. Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 8815-8820.
37. Ashwell, G. J.; Mohib, A. Improved Molecular Rectification from Self-Assembled Monolayers of a Sterically Hindered Dye. J. Am. Chem. Soc. 2005, 127, 16238-16244.
38. Nerngchamnong, N.; Yuan, L.; Qi, D.-C.; Li, J.; Thompson, D.; Nijhuis, C. A. The Role of van der Waals Forces in the Performance of Molecular Diodes. Nat. Nanotechnol. 2013, 8, 113-118.
39. Lortscher, E.; Gotsmann, B.; Lee, Y.; Yu, L. P.; Retter, C.; Riel, H. Transport Properties of a Single-Molecule Diode. ACS Nano 2012, 6, 4931-4939.
40. Zhou, C.; Deshpande, M. R.; Reed, M. A.; Jones, L.; Tour, J. M. Nanoscale Metal Self-assembled Monolayer Metal Heterostructures. Appl. Phys. Lett. 1997, 71, 611-613.
41. Kalakodimi, R. P.; Nowak, A. M.; McCreery, R. L. Carbon/Molecule/Metal and Carbon/Molecule/Metal Oxide Molecular Electronic Junctions. Chem. Mater. 2005, 17, 4939-4948.
42. Choi, S. H.; Kim, B.; Frisbie, C. D. Electrical Resistance of Long Conjugated Molecular Wires. Science 2008, 320, 1482-1486.
43. Choi, S. H.; Risko, C.; Ruiz Delgado, M. C.; Kim, B.; Bredas, J.-L.; Frisbie, C. D. Transition from Tunneling to Hopping Transport in Long, Conjugated Oligo-imine Wires Connected to Metals. J. Am. Chem. Soc. 2010, 132, 4358-4368.
44. Tedde, S. F.; Kern, J.; Sterzl, T.; Furst, J.; Lugli, P.; Hayden, O. Fully Spray Coated Organic Photodiodes. Nano Lett. 2009, 9, 980-983.
45. Pandey, R.; Holmes, R. J. Graded Donor-Acceptor Heterojunctions for Efficient Organic Photovoltaic Cells. Adv. Mater. 2010, 22, 5301-5305.
46. Falco, A.; Cina, L.; Scarpa, G.; Lugli, P.; Abdellah, A. Fully-Sprayed and Flexible Organic Photodiodes with Transparent Carbon Nanotube Electrodes. ACS Appl. Mater. Interfaces 2014, 6, 10593-10601.
47. Kim, Y.; Cook, S.; Tuladhar, S. M.; Choulis, S. A.; Nelson, J.; Durrant, J. R.; Bradley, D. D. C.; Giles, M.; McCulloch, I.; Ha, C. S.; et al. Strong Regioregularity Effect in Self-Organizing Conjugated Polymer Films and High-Efficiency Polythiophene: Fullerene Solar Cells. Nat. Mater. 2006, 5, 197-203.
48. Rosink, J. J. W. M.; Blauw, M. A.; Geerligs, L. J.; van der Drift, E.; Rousseeuw, B. A. C.; Radelaar, S.; Sloof, W. G.; Fakkeldij, E. J. M. Self-Assembly of π-Conjugated Azomethine Oligomers by Sequential Deposition of Monomers from Solution. Langmuir 2000, 16, 4547-4553.
49. Tuccitto, N.; Ferri, V.; Cavazzini, M.; Quici, S.; Zhavnerko, G.; Licciardello, A.; Rampi, M. A. Highly Conductive Similar to 40-nmlong Molecular Wires Assembled by Stepwise Incorporation of Metal Centres. Nat. Mater. 2009, 8, 41-46.
50. Luo, L.; Frisbie, C. D. Length-Dependent Conductance of Conjugated Molecular Wires Synthesized by Stepwise "Click" Chemistry. J. Am. Chem. Soc. 2010, 132, 8854-8855.
51. Ashwell, G. J.; Williams, A. T.; Barnes, S. A.; Chappell, S. L.; Phillips, L. J.; Robinson, B. J.; Urasinska-Wojcik, B.; Wierzchowiec, P.; Gentle, I. R.; Wood, B. J. Self-Assembly of Amino-Thiols via Gold- Nitrogen Links and Consequence for In Situ Elongation of Molecular Wires on Surface-Modified Electrodes. J. Phys. Chem. C 2011, 115, 4200-4208.
52. Ashwell, G. J.; Urasinska-Wojcik, B.; Phillips, L. J. In Situ Stepwise Synthesis of Functional Multijunction Molecular Wires on Gold Electrodes and Gold Nanoparticles. Angew. Chem., Int. Ed. 2010, 49, 3508-3512.
53. Wasielewski, M. R. Self-Assembly Strategies for Integrating Light Harvesting and Charge Separation in Artificial Photosynthetic Systems. Acc. Chem. Res. 2009, 42, 1910-1921.
54. Bryce, M. R. Functionalised Tetrathiafulvalenes: New Applications as Versatile π-Electron Systems in Materials Chemistry. J. Mater. Chem. 2000, 10, 589-598.
55. Segura, J. L.; Martin, N. New Concepts in Tetrathiafulvalene Chemistry. Angew. Chem., Int. Ed. 2001, 40, 1372-1409.
56. Tang, C. W. 2-Layer Organic Photovoltaic Cell. Appl. Phys. Lett. 1986, 48, 183-185.
57. Andreu, R.; Garin, J.; Orduna, J.; Saviron, M.; Cousseau, J.; Gorgues, A.; Morisson, V.; Nozdryn, T.; Becher, J.; Clausen, R. P.; Bryce, M. R.; Skabara, P. J.; Dehaen, W. The Synthesis of 4,4′(5′)-Diformyltetrathiafulvalene. Tetrahedron Lett. 1994, 35, 9243-9246.
58. Choi, S. H.; Frisbie, C. D. Enhanced Hopping Conductivity in Low Band Gap Donor-Acceptor Molecular Wires Up to 20 nm in Length. J. Am. Chem. Soc. 2010, 132, 16191-16201.
59. Neuber, C.; Bate, M.; Giesa, R.; Schmidt, H. W. Combinatorial Methods for the Optimization of the Vapor Deposition of Polyimide Monomers and Their Polymerization. J. Mater. Chem. 2006, 16, 3466-3477.
60. Becke, A. D. Density-Functional Thermochemistry 0.3. The Role of Exact Exchange. J. Chem. Phys. 1993, 98, 5648-5652.
61. Lee, C. T.; Yang, W. T.; Parr, R. G. Development of the Colle-Salvetti Correlation-Energy Formula into a Functional of the Electrondensity. Phys. Rev. B: Condens. Matter 1988, 37, 785-789.
62. Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Non-covalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals. Theor. Chem. Acc. 2008, 120, 215-241.
63. Peverati, R.; Truhlar, D. G. Improving the Accuracy of Hybrid Meta-GGA Density Functionals by Range Separation. J. Phys. Chem. Lett. 2011, 2, 2810-2817.
64. Harihara, Pc; Pople, J. A. Influence of Polarization Functions on Molecular-Orbital Hydrogenation Energies. Theor. Chim. Acta 1973, 28, 213-222.
65. Frisch, M. J. T., G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; et al. Gaussian09 ; Gaussian, Inc.: Wallingford, 2009.
66. Olson, R. M. M. A. V.; Chamberlin, A. C.; Kelly, C. P.; Thompson, J. D.; Xidos, J. D.; Li, J.; Hawkins, G. D.; Winget, P. D.; Zhu, T.; Rinaldi, D., et al. ; University of Minnesota: Minneapolis, MN, 2011.
67. Runge, E.; Gross, E. K. U. Density-Functional Theory for Time-Dependent Systems. Phys. Rev. Lett. 1984, 52, 997-1000.
68. Kim, J. Y.; Bard, A. J. Organic Donor/acceptor Heterojunction Photovoltaic Devices Based on Zinc Phthalocyanine and a Liquid Crystalline Perylene Diimide. Chem. Phys. Lett. 2004, 383, 11-15.
69. Pavlishchuk, V. V.; Addison, A. W. Conversion Constants for Redox Potentials Measured Versus Different Reference Electrodes in Acetonitrile Solutions at 25°C. Inorg. Chim. Acta 2000, 298, 97-102.
70. Hansen, W. N.; Hansen, G. J. Absolute Half-Cell Potential - A Simple Direct Measurement. Phys. Rev. A: At. Mol. Opt. Phys. 1987, 36, 1396-1402.
71. Engelkes, V. B.; Beebe, J. M.; Frisbie, C. D. 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. 2004, 126, 14287-14296.
72. Luo, L.; Benameur, A.; Brignou, P.; Choi, S. H.; Rigaut, S.; Frisbie, C. D. Length and Temperature Dependent Conduction of Ruthenium-Containing Redox-Active Molecular Wires. J. Phys. Chem. C 2011, 115, 19955-19961.
73. Wold, D. J.; Frisbie, C. D. Formation of Metal-Molecule-Metal Tunnel Junctions: Microcontacts to Alkanethiol Monolayers with a Conducting AFM Tip. J. Am. Chem. Soc. 2000, 122, 2970-2971.
74. Wold, D. J.; Frisbie, C. D. Fabrication and Characterization of Metal-Molecule-Metal Junctions by Conducting Probe Atomic Force Microscopy. J. Am. Chem. Soc. 2001, 123, 5549-5556.
75. Beebe, J. M.; Engelkes, V. B.; Miller, L. L.; Frisbie, C. D. Contact Resistance in Metal-Molecule-Metal Junctions Based on Aliphatic SAMs: Effects of Surface Linker and Metal Work Function. J. Am. Chem. Soc. 2002, 124, 11268-11269.
76. Wold, D. J.; Haag, R.; Rampi, M. A.; Frisbie, C. D. 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 2002, 106, 2813-2816.
77. Engelkes, V. B.; Beebe, J. M.; Frisbie, C. D. 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 2005, 109, 16801-16810.
78. Salomon, A.; Boecking, T.; Seitz, O.; Markus, T.; Amy, F.; Chan, C.; Zhao, W.; Cahen, D.; Kahn, A. What Is the Barrier for Tunneling through Alkyl Monolayers? Results from n- and p-Si-Alkyl/Hg Junctions. Adv. Mater. 2007, 19, 445-450.
79. Jin, Y.; Friedman, N.; Sheves, M.; Cahen, D. Effect of Metal-Molecule Contact Roughness on Electronic Transport: Bacteriorhodopsin-Based, Metal-Insulator-Metal Planar Junctions. Langmuir 2008, 24, 5622-5626.
80. 3/EGaIn Junctions. Chem. Mater. 2014, 26, 3938-3947.
81. Kornilovitch, P. E.; Bratkovsky, A. M.; Williams, R. S. Current Rectification by Molecules with Asymmetric Tunneling Barriers. Phys. Rev. B: Condens. Matter 2002, 66, 165436-1-165436-11.
82. Liu, R.; Ke, S. H.; Yang, W. T.; Baranger, H. U. Organometallic Molecular Rectification. J. Chem. Phys. 2006, 124, 024718-1-024718-5.