Geometry and electronic coupling in perylenediimide stacks: Mapping structure - charge transport relationships

Journal of the American Chemical Society

Volumn 132, Issue 6, 2010, Pages 1738-1739

  Vura Weis, Josh ^a   Ratner, Mark A ^a   Wasielewski, Michael R ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSPORT; CHEMICAL EQUATIONS; ELECTRONIC COUPLING; MAPPING STRUCTURES; ORDER OF MAGNITUDE; ORGANIC THIN FILM TRANSISTORS; PENTACENES; PERYLENEDIIMIDES; POLYTHIOPHENE DERIVATIVES;

CHEMICAL REACTIONS; GEOMETRY; NUCLEAR ENERGY; OLIGOMERS; POTENTIAL ENERGY; QUANTUM CHEMISTRY; THIN FILM TRANSISTORS; THIOPHENE;

BINDING ENERGY;

IMIDE; NANOCRYSTAL; PERYLENEDIIMIDE; UNCLASSIFIED DRUG;

ARTICLE; DENSITY FUNCTIONAL THEORY; ELECTRON TRANSPORT; ELECTRONICS; ENERGY; GEOMETRY; LIQUID CRYSTAL; NANOANALYSIS; SEMICONDUCTOR;

EID: 77249138299     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja907761e     Document Type: Article

References (28)

1. Organic Field-Effect Transistors; Bao, Z., Locklin, J., Eds.; CRC Press: Boca Raton, FL, 2007.
2. Huttner, S.; Sommer, M.; Thelakkat, M. Appl. Phys. Lett. 2008, 92, 093302.
3. Struijk, C. W.; Sieval, A. B.; Dakhorst, J. E. J.; van Dijk, M.; Kimkes, P.; Koehorst, R. B. M.; Donker, H.; Schaafsma, T. J.; Picken, S. J.; van de Craats, A. M.; Warman, J. M.; Zuilhof, H.; Sudholter, E. J. R. J. Am. Chem. Soc. 2000, 122, 11057-11066.
4. Zang, L.; Che, Y.; Moore, J. S. Acc. Chem. Res. 2008, 41, 1596-1608.
5. (a) Chesterfield, R. J.; McKeen, J. C.; Newman, C. R.; Ewbank, P. C.; da Silva, D. A.; Bredas, J. L.; Miller, L. L.; Mann, K. R.; Frisbie, C. D. J. Phys. Chem. B 2004, 108, 19281-19292.
6. (b) Oh, J. H.; Lee, H. W.; Mannsfeld, S.; Stoltenberg, R. M.; Jung, E.; Jin, Y. W.; Kim, J. M.; Yoo, J. B.; Bao, Z. N. Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 6065-6070.
7. (c) Briseno, A. L.; Mannsfeld, S. C. B.; Reese, C.; Hancock, J. M.; Xiong, Y.; Jenekhe, S.; Bao, Z.; Xia, Y. Nano Lett. 2007, 7, 2847. Crystal structures of some PDI OTFTs are not known. .
8. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215-241.
9. Hohenstein, E. G.; Chill, S. T.; Sherrill, C. D. J. Chem. Theory Comput. 2008, 4, 1996-2000.
10. (a) Fink, R. F.; Seibt, J.; Engel, V.; Renz, M.; Kaupp, M.; Lochbrunner, S.; Zhao, H.-M.; Pfister, J.; Würthner, F.; Engels, B. J. Am. Chem. Soc. 2008, 130, 12858-12859.
11. (b) Zhao, H.-M.; Pfister, J.; Settels, V.; Renz, M.; Kaupp, M.; Dehm, V. C.; Wurthner, F.; Fink, R. F.; Engels, B. J. Am. Chem. Soc. 2009, 131, 15660-15668.
12. Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553-566.
13. Shao, Y.; et al. Phys. Chem. Chem. Phys. 2006, 8, 3172-3191.
14. Bredas, J. L.; Beljonne, D.; Coropceanu, V.; Cornil, J. Chem. Rev. 2004, 104, 4971-5003.
15. Coropceanu, V.; Sánchez-Carrera, R. S.; Paramonov, P.; Day, G. M.; Brédas, J.-L. J. Phys. Chem. C 2009, 113, 4679-4686.
16. (a) Kazmaier, P. M.; Hoffman, R. J. Am. Chem. Soc. 1994, 116, 9684-9691.
17. (b) Feng, X. L.; Marcon, V.; Pisula, W.; Hansen, M. R.; Kirkpatrick, J.; Grozema, F.; Andrienko, D.; Kremer, K.; Mullen, K. Nat. Mater. 2009, 8, 421-426.
18. (c) Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2005, 127, 16866-16881.
19. (d) da Silva, D. A.; Kim, E. G.; Bredas, J. L. Adv. Mater. 2005, 17, 1072-1076.
20. (a) Klebe, G.; Graser, F.; Hadicke, E.; Berndt, J. Acta Crystallogr., Sect. B 1989, 45, 69-77.
21. (b) Hino, K.; Sato, K.; Takahashi, H.; Suzuki, S.; Mizuguchi, J. Acta Crystallogr. 2005, e61, o440-o441.
22. (c) Mizuguchi, J.; Hino, K.; Sato, K.; Suzuki, S. Acta Crystallogr. 2005, e61, o434-o436.
23. (d) Mizuguchi, J.; Hino, K.; Sato, K.; Takahashi, H. Acta Crystallogr. 2005, e61, o437-o439.
24. Monomers in 2, 18, and 20 are both translated and rotated in the stack, and are not shown on Figure 2.
25. The HOMO of this monomer contains a significant contribution from the methoxyphenyl orbitals, making the dimer-splitting model inappropriate. We thank Prof. Jean-Luc Bredas for alerting us to this.
26. Singh, T. B.; Erten, S.; Günes, S.; Zafer, C.; Turkmen, G.; Kuban, B.; Teoman, Y.; Sariciftci, N. S.; Icli, S. Org. Electron. 2006, 7, 480-489.
27. Cheng, Y. C.; Silbey, R. J.; da Silva, D. A.; Calbert, J. P.; Cornil, J.; Bredas, J. L. J. Chem. Phys. 2003, 118, 3764-3774.
28. Note that pentacene forms a herringbone structure, which requires a more complicated model; see discussion in the Supporting Information.