Quantum-chemical characterization of the origin of dipole formation at molecular organic/organic interfaces

Advanced Functional Materials

Volumn 19, Issue 4, 2009, Pages 624-633

  Avilov, Igor ^a   Geskin, Victor ^a   Cornil, Jérôme ^a  

^a UNIVERSITY OF MONS   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; CHEMICAL BONDS; ELECTRON AFFINITY; ION EXCHANGE; MASS TRANSFER; POLARIZATION; QUANTUM CHEMISTRY; VACUUM APPLICATIONS;

CHEMICAL CHARACTERIZATIONS; DONOR AND ACCEPTORS; ELECTRON ACCEPTORS; ELECTRON DONORS; ELECTRONIC COUPLINGS; FRACTIONAL CHARGES; INTERFACE DIPOLES; ISOLATED COMPOUNDS; MODEL SYSTEMS; ORGANIC MATERIALS; POLARIZATION EFFECTS; QUANTUM-CHEMICAL CALCULATIONS; STRONG-COUPLING REGIMES; TETRACYANOQUINODIMETHANE; TETRATHIAFULVALENE; TWO REGIMES; VACUUM LEVEL SHIFTS;

IONIZATION POTENTIAL;

EID: 61349096056     PISSN: 1616301X     EISSN: 16163028     Source Type: Journal    
DOI: 10.1002/adfm.200800632     Document Type: Article

References (45)

1. C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, Adv. Fund. Mater. 2001, 11, 15.
2. H. Ishii, K. Sugiyama, E. Ito, K. Seki, Adv. Mater. 1999, 11, 605.
3. C. Shen, A. Kahn, I. Hill, In Conjugated Polymer and Molecular Interfaces: Science and Technology for Photonic and Optoeledronic Applications (Eds: W. R. Salaneck, K, Sekl, A. Kahn, J.-J. Pireaux), Marcel Dekker, New York 2001, pp. 351-400.
4. S. C. Veenstra, H. T. Jonkman J. Polym. Sci. Part B 2003, 41, 2549.
5. D. Cahen, A. Kahn, Adv. Mater. 2003, 15, 271.
6. X. Crispin, V. Geskin, A. Crispin, J. Cornil, R. Lazzaroni, W. R. Salaneck, J.-L. Brédas, J. Am. Chem. Soc. 2002, 124, 8131.
7. D. Cornil, Y. Olivier, V. Geskin, J. Cornil, Adv. Funct. Mater. 2007, 17, 1143.
8. H. Vázquez, W. Cao, F. Flores, A. Kahn, Phys. Rev. B 2005, 71, 041306(R).
9. H. Vázquez, F. Flores, A. Kahn, In Proc. Int. Symp. Super-Fundionality Organic Devices, IPAP Conf. Series 6, The Institute of Pure and Applied Physics, Tokyo 2005, p. 1.
10. R. J. Murdey, W. R. Salaneck, Jpn. J. Appl. Phys. Part A 2005, 44, 3751.
11. R. S. Mulliken, W. B. Person, J. Am. Chem. Soc. 1969, 91, 3409.
12. M. J. S. Dewar, C. C. Thompson, Tetrahedron 1966, S7, 97.
13. K. Morokuma, Acc. Chem. Res. 1977, 10, 294.
14. C. J. Bender, Chem. Soc. Rev. 1986, 15, 475.
15. +). Thus, the larger the absolute value of the difference XD-XA, the more effective is the charge transfer from the donor to the acceptor with respect to the back CT (from the acceptor to the donor).
16. J.-L. Brédas, J. P. Calbert, D. A. da Silva Filho, J. Cornil, Proc. Natl. Acad. Sci. USA 2002, 99, 5804.
17. P. S. Bagus, V. Staemmler, C. Wöll, Phys. Rev. Lett. 2002, 89, 096104.
18. G. Witte, S. Lukas, P. S. Bagus, C. Wöll, Appl. Php. Lett. 2005, 87, 263502.
19. P. S. Bagus, G. Witte, C. Wöll J. Chem. Php. 2005, 123, 184109.
20. M. J. S. Dewar, E.G. Zoebisch, E. F. Healy, J. Am. Chem. Soc. 1985, 107, 3902.
21. M. J. S. Dewar, Y.-C. Yuan, Inorg. Chem. 1990, 29, 3881.
22. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
23. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785.
24. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. N. Kudin, J. C. Burant.J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmanl, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavacharl, J. B. Foresman, J. V. Ortiz, Q. Cui, A. C. Baboul, S. Clifford, J. Closlowskl, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham,C. Y. Peng, A. Nanayakkara, M.Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision C.02; Gaussian, Inc, Wallingford, CT 2004.
25. W. J. Hehre, R. Ditchfield, J. A. PopleJ. Chem. Phys. 1972, 56, 2257.
26. S. M. Bachrach, in Computational Organic Chemistry, Vol. 5(Eds: K. B. Lipkowitz, D. B. Boyd), VCH, New York 1994, pp. 171-227.
27. S. F. Boys, F. Bernardi, Mol. Phys. 1970, 19, 553.
28. W. Osikowicz, M. P. de Jong, W. R. Salaneck, Adv. Mater. 2007, 19, 4213.
29. H. Vázquez, R. Oszwaldowski, P. Pou, J. Ortega, R. Pérez. F. Flores, A. Kahn, Europhys. Lett. 2004, 65, 802.
30. H. Vázquez, F. Flores, R. Oszwaldowski, J. Ortega, R. Peréz, A. Kahn, Appl. Surf. Sci. 2004, 234, 107.
31. H. Vázquez, F. Flores, A. Kahn, Org. Electron. 2007, 8, 241.
32. C. Tengstedt, W. Osikowicz, W. R. Salaneck, I. D. Parker, C.-H. Hsu, M. Fahlman, Appl. Phys. Lett. 2006, 88, 053502.
33. A. Crispin, X. Crispin, M. Fahlman, M. Berggren, W. R. Salaneck, Appl. Phys. Lett. 2006, 89, 213503.
34. S. Braun, W. Osikowicz, Y. Wang, W. R. Salaneck, Org. Electron. 2007, 8, 14.
35. S. Braun, W. R. Salaneck, Chem. Phys. Lett. 2007, 438, 259.
36. E. V. Tslper, Z. G. Soos, W. Gaob, A. Kahn, Chem. Phys. Lett. 2002, 360, 47.
37. U. Salzner, P. G. Pickup, R. A. Poirier, J. B. Lagowski, J. Phys. Chem. A 1998, 102, 2572.
38. E. Ruiz, D. R. Salahub, A. Vela, J. Php. Chem. 1996, 100, 12265.
39. J. C. Sancho-García, Chem. Phys. 2007, 331, 321.
40. Y. Zhao, D. G. Truhlar, J. Chem. Theory Comput. 2005, 1, 415.
41. J. Ridley, M. C. Zerner, Theor. Chim. Acta 1973, 32, 111.
42. A. Van Vooren, V. Lemaur, A. Ye, D. Beljonne, J. Cornil, ChemPhysChem 2007, 8, 1240.
43. V. Lemaur, D. A. da Silva Filho, V. Coropceanu. M. Lehmann, Y. Geerts, J. Piris, M. G. Debije, A. M. van de Craats, K. Senthilkumar, L. D. A. Siebbeles, J. M. Warman, J.-L. Brédas, J. Cornil, J. Am. Chem. Soc. 2004, 126, 3271.
44. A. Rajagopal, C. I. Wu, A. Kahn J. Appl. Phys. 1998, 83, 2649.
45. R. J. Murdey, unpublished.