Substituent effects on the electronic characteristics of pentacene derivatives for organic electronic devices: Dioxolane-substituted pentacene derivatives with triisopropylsilylethynyl functional groups

Journal of the American Chemical Society

Volumn 134, Issue 34, 2012, Pages 14185-14194

  Griffith, Olga Lobanova ^a   Anthony, John E ^b   Jones, Adolphus G ^b   Shu, Ying ^b   Lichtenberger, Dennis L ^a  

^a University of Arizona   (United States)

^b UNIVERSITY OF KENTUCKY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONDENSED PHASE; ELECTROCHEMICAL MEASUREMENTS; ELECTRON TRANSFER; ELECTRONIC BEHAVIORS; ELECTRONIC CHARACTERISTICS; ELECTRONIC EFFECTS; ELECTRONIC INTERACTIONS; ELECTRONIC STRUCTURE CALCULATIONS; FUNCTIONALIZATIONS; GASPHASE; HOMO-LUMO ENERGY GAP; INTERMOLECULAR INTERACTIONS; MATERIAL BEHAVIOR; ORGANIC ELECTRONIC DEVICES; PENTACENE FILM; PENTACENES; POLARIZATION EFFECT; POLARIZATION ENERGY; RELATIVE ELECTRICAL CONDUCTIVITIES; REORGANIZATION ENERGIES; SOLID-PHASE; SUBSTITUENT EFFECT; TIPS-PENTACENE; TRANSFER PROPERTIES;

CHARGE TRANSFER; ELECTRIC CONDUCTIVITY; ELECTRONIC STRUCTURE; FUNCTIONAL GROUPS; IONIZATION POTENTIAL; PHOTOELECTRON SPECTROSCOPY; POLARIZATION;

MOLECULES;

2,2,10,10 TETRAETHYL 6,14 BIS(TRIISOPROPYLSILYLETHYNYL) 1,3,9,11 TETRAOXA DICYCLOPENTA[B,M]PENTACENE; 6,13 BIS(TRIISOPROPYLSILYLETHYNYL)PENTACENE; 6,14 BIS(TRIISOPROPYLSILYLETHYNYL) 1,3,9,11 TETRAOXA DICYCLOPENTA[B,M]PENTACENE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ELECTRICITY; ELECTROCHEMISTRY; ELECTRON TRANSPORT; ELECTRONICS; ENERGY; IONIZATION; MOLECULAR INTERACTION; POLARIZATION; X RAY PHOTOELECTRON SPECTROSCOPY;

EID: 84865614116     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3056672     Document Type: Article

References (60)

1. Lane, P. A.; Palilis, L. C.; Kushto, G. P.; Kafafi, Z. H.; Purushothaman, B.; Anthony, J. E. Proc. SPIE 2008, 7052, 70521J/1-70521J/6
2. Lin, Y.; Gundlach, D. J.; Nelson, S. F.; Jackson, T. N. IEEE Trans. Electron Devices 1997, 44, 1325-1331
3. Palilis, L. C.; Lane, P. A.; Kushto, G. P.; Purushothaman, B.; Anthony, J. E.; Kafafi, Z. H. Org. Electron. 2008, 9, 747-752
4. Park, S. K.; Jackson, T. N.; Anthony, J. E.; Mourey, D. A. Appl. Phys. Lett. 2007, 91, 063514/1-063514/3
5. Payne, M. M.; Parkin, S. R.; Anthony, J. E.; Kuo, C.; Jackson, T. N. J. Am. Chem. Soc. 2005, 127, 4986-4987
6. Platt, A. D.; Day, J.; Subramanian, S.; Anthony, J. E.; Ostroverkhova, O. J. Phys. Chem. C 2009, 113, 14006-14014
7. Sakamoto, Y.; Suzuki, T.; Kobayashi, M.; Gao, Y.; Inoue, Y.; Tokito, S. Mol. Cryst. Liq. Cryst. 2006, 444, 225-232
8. Singh, T. B.; Meghdadi, F.; Guenes, S.; Marjanovic, N.; Horowitz, G.; Lang, P.; Bauer, S.; Sariciftci, N. S. Adv. Mater. (Weinheim, Ger.) 2005, 17, 2315-2320
9. Tang, C. W.; Vanslyke, S. A. Appl. Phys. Lett. 1987, 51, 913-915
10. Wolak, M. A.; Delcamp, J.; Landis, C. A.; Lane, P. A.; Anthony, J. E.; Kafafi, Z. Adv. Funct. Mater. 2006, 16, 1943-1949
11. Kelley, T. W.; Muyres, D. V.; Baude, P. F.; Smith, T. P.; Jones, T. D. Mater. Res. Soc. Symp. Proc. 2003, 771, 169-179
12. Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048
13. Lane, P. A.; Kafafi, Z. H. Solid-State Photovoltaics: A Review of Molecular and Polymeric Devices. In Organic Photovoltaics: Mechanism, Materials, and Devices; Sun, S.-S.; Sariciftci, N. S, Eds.; CRC Press: Boca Raton, FL, 2005; Vol. 99, pp 49-104.
14. Giri, G.; Verploegen, E.; Mannsfeld, S. C. B.; Atahan-Evrenk, S.; Kim, D. H.; Lee, S. Y.; Becerril, H. A.; Aspuru-Guzik, A.; Toney, M. F.; Bao, Z. Nature 2011, 480, 504-508
15. Han, J.; Bae, I.; Chung, I. ECS Trans. 2011, 33, 101-111
16. Anthony, J. E. In Functional Organic Materials: Syntheses, Strategies and Applications; Mueller, T. J. J.; Bunz, U. H. F., Eds.; Wiley-VCH: Chichester, 2007; Chapter 4, pp 511-545.
17. Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001, 123, 9482-9483
18. Anthony, J. E.; Purushothaman, B. Proc. SPIE 2007, 6658, 66580L/1-66580L/8
19. Anthony, J. E. Angew.Chem., Int. Ed. 2008, 47, 452-483
20. Wolak, M. A.; Melinger, J. S.; Lane, P. A.; Palilis, L. C.; Landis, C. A.; Delcamp, J.; Anthony, J. E.; Kafafi, Z. H. J. Phys. Chem. B 2006, 110, 7928-7937
21. Wolak, M. A.; Melinger, J. S.; Lane, P. A.; Palilis, L. C.; Landis, C. A.; Anthony, J. E.; Kafafi, Z. H. J. Phys. Chem. B 2006, 110, 10606-10611
22. Siegbahn, K.; Nordling, C.; Fahlman, A.; Nordberg, R.; Hamrin, K.; Hedman, J.; Johansson, G.; Bergmark, T.; Karlsson, S. E.; Lindgren, I.; Lindberg, B. Nova Acta Regiae Soc. Sci. Ups. 1967, 20, 282
23. Lichtenberger, D. L.; Kellogg, G. E.; Kristofzski, J. G.; Page, D.; Turner, S.; Klinger, G.; Lorenzen, J. Rev. Sci. Instrum. 1986, 57, 2366
24. Cranswick, M. A.; Dawson, A.; Cooney, J. J. A.; Gruhn, N. E.; Lichtenberger, D. L.; Enemark, J. H. Inorg. Chem. 2007, 46, 10639-10646
25. Li, Y.; Cao, Y.; Gao, J.; Wang, D.; Yu, G.; Heeger, A. J. Synth. Met. 1999, 99, 243-248
26. de Leeuw, D. M.; Simenon, M. M. J.; Brown, A. R.; Einerhand, R. E. F. Synth. Met. 1997, 87, 53-59
27. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03; Gaussian, Inc.: Wallingford, CT, 2004. http://www.gaussian.com. See the program documentation on the web site for the definitions and original references to the density functionals, basis sets, and other details of the computational models used in this study.
28. ADF2008.01. SCM, Theoretical Chemistry; Vrije Universiteit: Amsterdam, The Netherlands, 2008; http://www.scm.com. See the program documentation on the web site for the definitions and original references to the density functionals, basis sets, and other details of the computational models used in this study.
29. MacroModel, Version 9.9; Schrödinger, LLC: New York, NY, 2011; http://www.schrodinger.com.
30. Delgado, M. C. R.; Pigg, K. R.; da Silva Filho, D. A.; Gruhn, N. E.; Sakamoto, Y.; Suzuki, T.; Osuna, R. M.; Casado, J.; Hernández, V.; Navarrete, J. T. L.; Martinelli, N. G.; Cornil, J.; Sánchez-Carrera, R. S.; Coropceanu, V.; Brédas, J. J. Am. Chem. Soc. 2009, 131, 1502-1512
31. Kaur, I.; Jia, W.; Kopreski, R. P.; Selvarasah, S.; Dokmeci, M. R.; Pramanik, C.; McGruer, N. E.; Miller, G. P. J. Am. Chem. Soc. 2008, 130, 16274-16286
32. Coropceanu, V.; Malagoli, M.; da Silva Filho, D. A.; Gruhn, N. E.; Bill, T. G.; Bredas, J. L. Phys. Rev. Lett. 2002, 89, 275503/1-275503/4
33. Griffith, O. L.; Gruhn, N. E.; Anthony, J. E.; Purushothaman, B.; Lichtenberger, D. L. J. Phys. Chem. C 2008, 112, 20518-20524
34. Gruhn, N. E.; da Silva Filho, D. A.; Bill, T. G.; Malagoli, M.; Coropceanu, V.; Kahn, A.; Bredas, J. J. Am. Chem. Soc. 2002, 124, 7918-7919
35. Lichtenberger, D. L.; Copenhaver, A. S. J. Electron Spectrosc. Relat. Phenom. 1990, 50, 335-352
36. Amashukeli, X.; Gruhn, N. E.; Lichtenberger, D. L.; Winkler, J. R.; Gray, H. B. J. Am. Chem. Soc. 2004, 126, 15566-15571
37. Malagoli, M.; Coropceanu, V.; da Silva Filho, D. A.; Bredas, J. L. J. Chem. Phys. 2004, 120, 7490-7496
38. Clark, P. A.; Brogli, F.; Heilbronner, E. Helv. Chim. Acta 1972, 55, 1415-1428
39. Gleiter, R.; Haider, R.; Quast, H. J. Chem. Res. 1978, 4, 138-139
40. Gleiter, R.; Hoffmann, H.; Irngartinger, H.; Nixdorf, M. Chem. Ber. 1994, 127, 2215-2224
41. Gleiter, R.; Uschmann, J. J. Org. Chem. 1986, 51, 370-380
42. Parker, V. D. J. Am. Chem. Soc. 1976, 98, 98-103
43. Vannucci, A. K.; Snyder, R. A.; Gruhn, N. E.; Lichtenberger, D. L.; Enemark, J. H. Inorg. Chem. (Washington, DC, U. S.) 2009, 48, 8856-8862
44. Graff, J. N.; McElhaney, A. E.; Basu, P.; Gruhn, N. E.; Chang, C. J.; Enemark, J. H. Inorg. Chem. 2002, 41, 2642-2647
45. Neikam, W. C.; Dimeler, G. R.; Desmond, M. M. J. Electrochem. Soc. 1964, 111, 1190-1192
46. Matsumura-Inoue, T.; Kuroda, K.; Umezawa, Y.; Achiba, Y. J. Chem. Soc., Faraday Trans. 2 1989, 85, 857-866
47. Griffith, O. L.; Anthony, J. E.; Jones, A. G.; Lichtenberger, D. L. J. Am. Chem. Soc. 2010, 132, 580-586
48. Cahen, D.; Kahn, A. Adv. Mater. 2003, 15, 271-277
49. Amy, F.; Chan, C.; Kahn, A. Org. Electron. 2005, 6, 85-91
50. Kang, S. J.; Yi, Y.; Kim, C. Y.; Cho, S. W.; Noh, M.; Jeong, K.; Whang, C. N. Synth. Met. 2006, 156, 32-37
51. Kahn, A.; Koch, N.; Gao, W. J. Polym. Sci., Part B: Polym. Phys. 2003, 41, 2529-2548
52. Ishii, H.; Sugiyama, K.; Ito, E.; Seki, K. Adv. Mater. 1999, 11, 605-625
53. Griffith, O. L.; Jones, A. G.; Anthony, J. E.; Lichtenberger, D. L. J. Phys. Chem. C 2010, 114, 13838-13845
54. Sato, N.; Seki, K.; Inokuchi, H. J. Chem. Soc., Faraday Trans. 2 1981, 77, 1621-1633
55. Sato, N.; Inokuchi, H.; Silinsh, E. A. Chem. Phys. 1987, 115, 269-277
56. Sansonetti, J. E.; Martin, W. C. J. Phys. Chem. Ref. Data 2005, 34, 1559-2259
57. Bruetting, W., Ed.; In Physics of Organic Semiconductors; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2005.
58. Koch, N.; Kahn, A.; Ghijsen, J.; Pireaux, J.; Schwartz, J.; Johnson, R. L.; Elschner, A. Appl. Phys. Lett. 2003, 82, 70-72
59. Schroeder, P. G.; France, C. B.; Park, J. B.; Parkinson, B. A. J. Phys. Chem. B 2003, 107, 2253-2261
60. Mori, T.; Fujikawa, H.; Tokito, S.; Taga, Y. Appl. Phys. Lett. 1998, 73, 2763-2765