Energy level realignment in weakly interacting donor-acceptor binary molecular networks

ACS Nano

Volumn 8, Issue 2, 2014, Pages 1699-1707

  Zhong, Jian Qiang ^a   Qin, Xinming ^b   Zhang, Jia Lin ^a   Kera, Satoshi ^c   Ueno, Nobuo ^c   Wee, Andrew Thye Shen ^a   Yang, Jinlong ^b   Chen, Wei ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

^c CHIBA UNIVERSITY   (Japan)

Author keywords

binary molecular superstructures; energy level alignment; gap states; scanning tunneling microscopy; self assembly; ultraviolet photoelectron spectroscopy; weak intermolecular interactions

Indexed keywords

EID: 84894633279     PISSN: 19360851     EISSN: 1936086X     Source Type: Journal    
DOI: 10.1021/nn406050e     Document Type: Article

References (49)

1. Zhang, J. L.; Niu, T. C.; Wee, A. T. S.; Chen, W. Self-Assembly of Binary Molecular Nanostructure Arrays on Graphite Phys. Chem. Chem. Phys. 2013, 15, 12414-12427
2. Ratner, M. A Brief History of Molecular Electronics Nat. Nanotechnol. 2013, 8, 378-381
3. Grill, L.; Dyer, M.; Lafferentz, L.; Persson, M.; Peters, M. V.; Hecht, S. Nano-architectures by Covalent Assembly of Molecular Building Blocks Nat. Nanotechnol. 2007, 2, 687-691
4. Zwaneveld, N. A. A.; Pawlak, R. M.; Abel, M.; Catalin, D.; Gigmes, D.; Bertin, D.; Porte, L. Organized Formation of 2D Extended Covalent Organic Frameworks at Surfaces J. Am. Chem. Soc. 2008, 130, 6678-6679
5. Pawin, G.; Wong, K. L.; Kwon, K.-Y.; Bartels, L. A Homomolecular Porous Network at a Cu(111) Surf. Sci. 2006, 313, 961-962
6. Schnadt, J.; Rauls, E.; Xu, W.; Vang, R. T.; Knudsen, J.; Lægsgaard, E.; Li, Z.; Hammer, B.; Besenbacher, F. Extended One-Dimensional Supramolecular Assembly on a Stepped Surface Phys. Rev. Lett. 2008, 100, 046103
7. Mao, J.; Zhang, H.; Jiang, Y.; Pan, Y.; Gao, M.; Xiao, W.; Gao, H. J. Tunability of Supramolecular Kagome Lattices of Magnetic Phthalocyanines Using Graphene-Based Moiré Patterns as Templates J. Am. Chem. Soc. 2009, 131, 14136-14137
8. Tahara, K.; Lei, S.; Adisoejoso, J.; De Feyter, S.; Tobe, Y. Supramolecular Surface-Confined Architectures Created by Self-Assembly of Triangular Phenylene-Ethynylene Macrocycles via Van Der Waals Interaction Chem. Commun. 2010, 46, 8507-8525
9. Huang, Y. L.; Chen, W.; Li, H.; Ma, J.; Pflaum, J.; Wee, A. T. S. Tunable Two-Dimensional Binary Molecular Networks Small 2010, 6, 70-75
10. Huang, Y. L.; Li, H.; Ma, J.; Huang, H.; Chen, W.; Wee, A. T. S. Scanning Tunneling Microscopy Investigation of Self-Assembled CuPc/F16CuPc Binary Superstructures on Graphite Langmuir 2009, 26, 3329-3334
11. Huang, Y. L.; Chen, W.; Wee, A. T. S. Molecular Trapping on Two-Dimensional Binary Supramolecular Networks J. Am. Chem. Soc. 2010, 133, 820-825
12. Niu, T. C.; Huang, Y. L.; Sun, J. T.; Kera, S.; Ueno, N.; Wee, A. T. S.; Chen, W. Tunable Two-Dimensional Molecular Dipole Dot Arrays on Graphite Appl. Phys. Lett. 2011, 99, 143114
13. de Oteyza, D. G.; Silanes, I.; Ruiz-Osés, M.; Barrena, E.; Doyle, B. P.; Arnau, A.; Dosch, H.; Wakayama, Y.; Ortega, J. E. Balancing Intermolecular and Molecule-Substrate Interactions in Supramolecular Assemblies Adv. Funct. Mater. 2009, 19, 259-264
14. 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
15. Isono, T.; Kamo, H.; Ueda, A.; Takahashi, K.; Nakao, A.; Kumai, R.; Nakao, H.; Kobayashi, K.; Murakami, Y.; Mori, H. Hydrogen Bond-promoted Metallic State in a Purely Organic Single-Component Conductor under Pressure Nat. Commun. 2013, 4, 1344
16. El-Sayed, A.; Mowbray, D. J.; García-Lastra, J. M.; Rogero, C.; Goiri, E.; Borghetti, P.; Turak, A.; Doyle, B. P.; Dell'Angela, M.; Floreano, L. et al. Supramolecular Environment-Dependent Electronic Properties of Metal-Organic Interfaces J. Phys. Chem. C 2012, 116, 4780-4785
17. Ruiz-Osés, M.; de Oteyza, D. G.; Fernández-Torrente, I.; Gonzalez-Lakunza, N.; Schmidt-Weber, P. M.; Kampen, T.; Horn, K.; Gourdon, A.; Arnau, A.; Ortega, J. E. Non-Covalent Interactions in Supramolecular Assemblies Investigated with Electron Spectroscopies ChemPhysChem 2009, 10, 896-900
18. de Oteyza, D. G.; García-Lastra, J. M.; Corso, M.; Doyle, B. P.; Floreano, L.; Morgante, A.; Wakayama, Y.; Rubio, A.; Ortega, J. E. Customized Electronic Coupling in Self-Assembled Donor-Acceptor Nanostructures Adv. Funct. Mater. 2009, 19, 3567-3573
19. Cabellos, J. L.; Mowbray, D. J.; Goiri, E.; El-Sayed, A.; Floreano, L.; de Oteyza, D. G.; Rogero, C.; Ortega, J. E.; Rubio, A. Understanding Charge Transfer in Donor-Acceptor/Metal Systems: A Combined Theoretical and Experimental Study J. Phys. Chem. C 2012, 116, 17991-18001
20. El-Sayed, A.; Borghetti, P.; Goiri, E.; Rogero, C.; Floreano, L.; Lovat, G.; Mowbray, D. J.; Cabellos, J. L.; Wakayama, Y.; Rubio, A. et al. Understanding Energy-Level Alignment in Donor-Acceptor/Metal Interfaces from Core-Level Shifts ACS Nano 2013, 7, 6914-6920
21. Amsalem, P.; Niederhausen, J.; Frisch, J.; Wilke, A.; Bröker, B.; Vollmer, A.; Rieger, R.; Müllen, K.; Rabe, J. R. P.; Koch, N. Metal-to-Acceptor Charge Transfer through a Molecular Spacer Layer J. Phys. Chem. C 2011, 115, 17503-17507
22. Niederhausen, J.; Amsalem, P.; Wilke, A.; Schlesinger, R.; Winkler, S.; Vollmer, A.; Rabe, J. P.; Koch, N. Doping of C60 Monolayers by Fermi-Level Pinning Induced Electron Transfer Phys. Rev. B 2012, 86, 081411
23. Ortmann, F.; Schmidt, W. G.; Bechstedt, F. Attracted by Long-Range Electron Correlation: Adenine on Graphite Phys. Rev. Lett. 2005, 95, 186101
24. Zhong, J. Q.; Mao, H. Y.; Wang, R.; Qi, D. C.; Cao, L.; Wang, Y. Z.; Chen, W. Effect of Gap States on the Orientation-Dependent Energy Level Alignment at the DIP/F16CuPc Donor-Acceptor Heterojunction Interfaces J. Phys. Chem. C 2011, 115, 23922-23928
25. Yamane, H.; Yabuuchi, Y.; Fukagawa, H.; Kera, S.; Okudaira, K. K.; Ueno, N. Does the Molecular Orientation Induce an Electric Dipole in Cu-Phthalocyanine Thin Films? J. Appl. Phys. 2006, 99, 093705
26. Fukagawa, H.; Kera, S.; Kataoka, T.; Hosoumi, S.; Watanabe, Y.; Kudo, K.; Ueno, N. The Role of the Ionization Potential in Vacuum-Level Alignment at Organic Semiconductor Interfaces Adv. Mater. 2007, 19, 665-668
27. Fukagawa, H.; Yamane, H.; Kera, S.; Okudaira, K. K.; Ueno, N. Experimental Estimation of the Electric Dipole Moment and Polarizability of Titanyl Phthalocyanine Using Ultraviolet Photoelectron Spectroscopy Phys. Rev. B 2006, 73, 041302
28. Zhong, S.; Zhong, J. Q.; Mao, H. Y.; Zhang, J. L.; Lin, J. D.; Chen, W. The Role of Gap States in the Energy Level Alignment at the Organic-Organic Heterojunction Interfaces Phys. Chem. Chem. Phys. 2012, 14, 14127-14141
29. Bussolotti, F.; Kera, S.; Kudo, K.; Kahn, A.; Ueno, N. Gap states in Pentacene Thin Film Induced by Inert Gas Exposure Phys. Rev. Lett. 2013, 110, 267602
30. Sueyoshi, T.; Fukagawa, H.; Ono, M.; Kera, S.; Ueno, N. Low-Density Band-Gap States in Pentacene Thin Films Probed with Ultrahigh-Sensitivity Ultraviolet Photoelectron Spectroscopy Appl. Phys. Lett. 2009, 95, 183303
31. Sueyoshi, T.; Kakuta, H.; Ono, M.; Sakamoto, K.; Kera, S.; Ueno, N. Band Gap States of Copper Phthalocyanine Thin Films Induced by Nitrogen Exposure Appl. Phys. Lett. 2010, 96, 093303
32. Otero, R.; Schöck, M.; Molina, L. M.; Lægsgaard, E.; Stensgaard, I.; Hammer, B.; Besenbacher, F. Guanine Quartet Networks Stabilized by Cooperative Hydrogen Bonds Angew. Chem., Int. Ed. 2005, 44, 2270-2275
33. Grobosch, M.; Mahns, B.; Loose, C.; Friedrich, R.; Schmidt, C.; Kortus, J.; Knupfer, M. Identification of the Electronic States of Manganese Phthalocyanine Close to the Fermi Level Chem. Phys. Lett. 2011, 505, 122-125
34. Ren, J.; Meng, S.; Wang, Y.-L.; Ma, X.-C.; Xue, Q.-K.; Kaxiras, E. Properties of Copper (Fluoro-)phthalocyanine Layers Deposited on Epitaxial Graphene J. Chem. Phys. 2011, 134, 194706-10
35. Grimme, S. Do Special Noncovalent π-π Stacking Interactions Really Exist? Angew. Chem., Int. Ed. 2008, 47, 3430-3434
36. Lau, K. M.; Tang, J. X.; Sun, H. Y.; Lee, C. S.; Lee, S. T.; Yan, D. Interfacial Electronic Structure of Copper Phthalocyanine and Copper Hexadecafluorophthalocyanine Studied by Photoemission Appl. Phys. Lett. 2006, 88, 173513-3
37. 16CuPc Interface J. Appl. Phys. 2001, 90, 4549-4554
38. Hill, I. G.; Kahn, A. Energy Level Alignment at Interfaces of Organic Semiconductor Heterostructures J. Appl. Phys. 1998, 84, 5583-5586
39. Lange, I.; Blakesley, J. C.; Frisch, J.; Vollmer, A.; Koch, N.; Neher, D. Band Bending in Conjugated Polymer Layers Phys. Rev. Lett. 2011, 106, 216402
40. Zhong, J. Q.; Huang, H.; Mao, H. Y.; Wang, R.; Zhong, S.; Chen, W. Molecular-Scale Investigation of C60/p-Sexiphenyl Organic Heterojunction Interface J. Chem. Phys. 2011, 134, 154706-6
41. 3/Organic Interface Energy Level Alignment Org. Electron. 2012, 13, 2793-2800
42. Kresse, G.; Hafner, J. Ab Initio Molecular Dynamics for Liquid Metals Phys. Rev. B 1993, 47, 558-561
43. Kresse, G.; Furthmüller, J. Efficient Iterative Schemes for ab Initio Total-energy Calculations Using A PPlane-Wave Basis Set Phys. Rev. B 1996, 54, 11169-11186
44. Kresse, G.; Furthmüller, J. Efficiency of ab-Initio Total Energy Calculations for Metals and Semiconductors Using a Plane-Wave Basis Set Comput. Mater. Sci. 1996, 6, 15-50
45. Blöchl, P. E. Projector Augmented-Wave Method Phys. Rev. B 1994, 50, 17953-17979
46. Kresse, G.; Joubert, D. From Ultrasoft Pseudopotentials to the Projector Augmented-Wave Method Phys. Rev. B 1999, 59, 1758-1775
47. Perdew, J. P.; Burke, K.; Ernzerhof, M. Generalized Gradient Approximation Made Simple Phys. Rev. Lett. 1996, 77, 3865-3868
48. Grimme, S. Semiempirical GGA-Type Density Functional Constructed with a Long-Range Dispersion Correction J. Comput. Chem. 2006, 27, 1787-1799
49. Monkhorst, H. J.; Pack, J. D. Special Points for Brillouin-Zone Integrations Phys. Rev. B 1976, 13, 5188-5192