Charge transfer in molecular complexes with 2,3,5,6-tetrafluoro-7,7,8,8- tetracyanoquinodimethane (F4-TCNQ): A density functional theory study

Chemistry of Materials

Volumn 23, Issue 23, 2011, Pages 5149-5159

  Zhu, Lingyun ^a   Kim, Eung Gun ^a,b   Yi, Yuanping ^a   Brédas, Jean Luc ^a,c  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b Dankook University   (South Korea)

^c KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

Author keywords

charge transfer; DFT; IP EA offset; molecular complexes; molecular doping; organic semiconductors

Indexed keywords

DFT; IP-EA OFFSET; MOLECULAR COMPLEXES; MOLECULAR DOPING; ORGANIC SEMICONDUCTOR;

CHARGE TRANSFER; ELECTRIC PROPERTIES; ELECTRON AFFINITY; IONIZATION POTENTIAL; SEMICONDUCTOR DOPING;

DENSITY FUNCTIONAL THEORY;

EID: 82955193847     PISSN: 08974756     EISSN: 15205002     Source Type: Journal    
DOI: 10.1021/cm201798x     Document Type: Article

References (69)

1. Walzer, K.; Maennig, B.; Pfeiffer, M.; Leo, K. Chem. Rev. 2007, 107, 1233
2. Koch, N. ChemPhysChem 2007, 8, 1438
3. Chan, C. K.; Zhao, W.; Kahn, A.; Hill, I. G. Appl. Phys. Lett. 2009, 94, 203306
4. Mulliken, R. S.; Person, W. B. Annu. Rev. Phys. Chem. 1962, 13, 107
5. Bender, C. J. Chem. Soc. Rev. 1986, 15, 475
6. Morokuma, K. Acc. Chem. Res. 1977, 10, 294
7. Yim, K.-H.; Whiting, G. L.; Murphy, C. E.; Halls, J. J. M.; Burroughes, J. H.; Friend, R. H.; Kim, J.-S. Adv. Mater. 2008, 20, 3319
8. Avilov, I.; Geskin, V.; Cornil, J. Adv. Funct. Mater. 2009, 19, 624
9. Toher, C.; Filippetti, A.; Sanvito, S.; Burke, K. Phys. Rev. Lett. 2005, 95, 146402
10. Zhang, Y.; de Boer, B.; Blom, P. W. M. Adv. Funct. Mater. 2009, 19, 1901
11. Gao, Z. Q.; Mi, B. X.; Xu, G. Z.; Wan, Y. Q.; Gong, M. L.; Cheah, K. W.; Chen, C. H. Chem. Commun. 2008, 117
12. Garnier, F.; Hajlaoui, R.; Yassar, A.; Srivastava, P. Science 1994, 265, 1684
13. Pfeiffer, M.; Leo, K.; Zhou, X.; Huang, J. S.; Hofmann, M.; Werner, A.; Blochwitz-Nimoth, J. Org. Electron. 2003, 4, 89
14. Huang, J.; Blochwitz-Nimoth, J.; Pfeiffer, M.; Leo, K. J. Appl. Phys. 2003, 93, 838
15. Zhou, Z.; Pfeiffer, M.; Blochwitz, J.; Werner, A.; Nollau, A.; Fritz, T.; Leo, K. Appl. Phys. Lett. 2001, 78, 410
16. Braun, K. F.; Hla, S. W. J. Chem. Phys. 2008, 129, 064707
17. Hwang, J.; Kahn, A. J. Appl. Phys. 2005, 97, 103705
18. Grimme, S. J. Comput. Chem. 2004, 25, 1463
19. Grimme, S. J. Comput. Chem. 2006, 27, 1787
20. Feyereisen, M.; Fitzgerald, G.; Komornicki, A. Chem. Phys. Lett. 1993, 208, 359
21. Scott, A. P.; Radom, L. J. Phys. Chem. 1996, 100, 16502
22. Senthilkumar, K.; Grozema, F. C.; Bichelhaupt, F. M.; Siebbeles, L. D. A. J. Chem. Phys. 2003, 119, 9809
23. Valeev, E. F.; Coropceanu, V.; da Silva Filho, D. A.; Salman, S.; Brédas, J.-L. J. Am. Chem. Soc. 2006, 128, 9882
24. Martin, R. L. J. Chem. Phys. 2003, 118, 4775
25. Dreuw, A.; Head-Gordon, M. Chem. Rev. 2005, 105, 4009
26. TURBOMOLE 6.0; TURBOMOLE GmbH: Karlsruhe, Germany, 2009.
27. Dovesi, R.; Saunders, V. R.; Roetti, C.; Orlando, R.; Zicovich-Wilson, C. M.; Harrison, N. M.; Doll, K.; Civalleri, B.; Bush, I. J.; D'Arco, P.; Llunell, M. CRYSTAL06; CRYSTAL Theoretical Chemistry Group: Torino, Italy, 2006.
28. Frisch, M. J., Gaussian03, E.01; Gaussian, Inc.: Wallingford, CT, 2004.
29. Jurečka, P.; Černý, J.; Hobza, P.; Valdés, H. J. Comput. Chem. 2006, 28, 555
30. Seponer, J.; Leszczynski, J.; Hobza, P. J. Comput. Chem. 1996, 17, 841
31. Zimmerli, U.; Parrinello, M.; Koumoutsakos, P. J. Chem. Phys. 2004, 120, 2693
32. Černý, J.; Jurečka, P.; Hobza, P.; Valdés, H. J. Phys. Chem. A 2007, 111, 1146
33. Wu, Q.; Yang, W. J. Chem. Phys. 2002, 116, 515
34. Hohenstein, E. G.; Chill, S. T.; Sherrill, C. D. J. Chem. Theory Comput. 2008, 4, 1996
35. Grimme, S.; Antony, J.; Ehrlich, S.; Krieg, H. J. Chem. Phys. 2010, 132, 154104
36. Guallar, V.; Borrelli, K. W. Proc. Natl. Acad. Sci. U.S.A 2005, 102, 3954
37. Alber, F.; Kuonen, O.; Scapozza, L.; Folkers, G.; Carloni, P. Proteins 1998, 31, 453
38. Černý, J.; Hobza, P. Phys. Chem. Chem. Phys. 2005, 7, 1624
39. Aziz, E. E.; Vollmer, A.; Eisebitt, S.; Eberhardt, W.; Pingel, P.; Neher, D.; Koch, N. Adv. Mater. 2007, 19, 3257
40. Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M. J. Chem. Phys. 2004, 120, 647
41. Grimme, S. Chem.-Eur. J. 2004, 10, 3423
42. Kistenmacher, T. J.; Emge, T. J.; Bloch, A. N.; Cowan, D. O. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1982, 38, 1193
43. Coppens, P.; Row, T. N. G. Ann. N.Y. Acad. Sci. 1978, 313, 244
44. Flandrois, S.; Chasseau, D. Acta Crystallogr., Sect. B: Struct. Commun. 1977, 33, 2744
45. Bozio, R.; Pecile, C. In Spectroscopy of Advanced Materials; Clark, R. J.; Hester, R. E., Eds.; Wiley: New York, 1991.
46. Maennig, B.; Pfeiffer, M.; Nollau, A.; Zhou, X.; Leo, K. Phys. Rev. B 2001, 64, 195208
47. Stires, J. C.; McLaurin, E. J.; Kubiak, C. P. Chem. Commun. 2005, 3532
48. Koch, N. Private communication.
49. Meneghetti, M.; Pecile, C. J. Chem. Phys. 1986, 84, 4149
50. Chappell, J. S.; Bloch, A. N.; Bryden, W. A.; Maxfield, M.; Poehler, T. O.; Cowan, D. O. J. Am. Chem. Soc. 1981, 103, 2443
51. Emge, T. J.; Maxfield, M.; Cowan, D. O.; Kistenmacher, T. J. Mol. Cryst. Liq. Cryst. 1981, 65, 161
52. Pingel, P.; Zhu, L.; Park, K. S.; Vogel, J.-O.; Janietz, S.; Kim, E.-G.; Rabe, J. P.; Brédas, J.-L.; Koch, N. J. Phys. Chem. Lett. 2010, 1, 2037
53. Cradock, S.; Huntley, C. M.; Rankin, D. W. H. J. Mol. Struct. 1988, 178, 217
54. Towler, M. D. Proceedings of HCM Network School Hartree-Fock Theory of the Electronic Structure of Solids, 1995.
55. Duhm, S.; Salzmann, I.; Broker, B.; Glowatzki, H.; Johnson, R. L.; Koch, N. Appl. Phys. Lett. 2009, 95, 093305
56. Zhou, X.; Blochwitz, J.; Pfeiffer, M.; Nollau, A.; Fritz, T.; Leo, K. Adv. Funct. Mater. 2001, 11, 310
57. Gao, W.; Kahn, A. Appl. Phys. Lett. 2001, 79, 4040
58. Sato, N.; Seki, K.; Inokuchi, H. J. Chem. Soc., Faraday Trans. 2 1981, 77, 1621
59. da Silva Filho, D. A.; Coropceanu, V.; Fichou, D.; Gruhn, N. E.; Bill, T. G.; Gierschner, J.; Cornil, J.; Brédas, J. L. Philos. Trans. R. Soc., A 2007, 365, 1435
60. Djurovich, P. I.; Mayo, E. I.; Forrest, S. R.; Thompson, M. E. Org. Electron. 2009, 10, 515
61. Chen, E. C. M.; Wentworth, W. E. J. Chem. Phys. 1975, 63, 3183
62. Telesca, R.; Bolink, H.; Yunoki, S.; Hadziioannou, G.; Van Duijnen, P. T.; Snijders, J. G.; Jonkman, H. T.; Sawatzky, G. A. Phys. Rev. B 2001, 63, 155112
63. Sánchez-Carrera, R. S.; Coropceanu, V.; da Silva Filho, D. A.; Friedlein, R.; Osikowicz, W.; Murdey, R.; Suess, C.; Salaneck, W. R.; Brédas, J.-L. J. Phys. Chem. B 2006, 110, 18904
64. Kim, E.-G.; Coropceanu, V.; Gruhn, N. E.; Sánchez-Carrera, R. S.; Snoeberger, R.; Matzger, A. J.; Brédas, J.-L. J. Am. Chem. Soc. 2007, 129, 13072
65. Kummel, S.; Kronik, L. Rev. Mod. Phys. 2008, 80, 3
66. Lee, J.-H.; Leem, D.-S.; Kim, H.-J.; Kim, J.-J. App. Phys. Lett. 2009, 94, 123306
67. Garcia, P.; Penuut, J. M.; Hapiot, P.; Wiatgens, V.; Vaht, P.; Gander, F.; Dehbouglise, D. J. Phys. Chem. 1993, 97, 513
68. Parr, R. G.; Pearson, R. G. J. Am. Chem. Soc. 1983, 105, 7512
69. Mulliken, R. S. J. Chem. Phys. 1934, 2, 782