Preparation and characterization of π-stacking quinodimethane oligothiophenes. Predicting semiconductor behavior and bandwidths from crystal structures and molecular orbital calculations

Journal of the American Chemical Society

Volumn 126, Issue 46, 2004, Pages 15295-15308

  Janzen, Daron E ^a   Burand, Michael W ^a   Ewbank, Paul C ^a   Pappenfus, Ted M ^a   Higuchi, Hiroyuki ^b   Da Silva Filho, Demetrio A ^c   Young, Victor G ^a   Brédas, Jean Luc ^c   Mann, Kent R ^a  

^a University of Minnesota   (United States)

^b UNIVERSITY OF TOYAMA   (Japan)

^c GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BAND STRUCTURE; BANDWIDTH; CRYSTAL STRUCTURE; DERIVATIVES; ELECTRON MOBILITY; HOLE MOBILITY; METHANE; OXIDATION; SUBSTITUTION REACTIONS; THIN FILM TRANSISTORS; ULTRAVIOLET SPECTROSCOPY; X RAY ANALYSIS;

COFACIAL STACKING; ELECTRONIC BAND STRUCTURE; MOLECULAR ORBITAL CALCULATIONS;

OLIGOMERS;

OLIGOMER; QUINODIMETHANE OLIGOTHIOPHENE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROSCOPY; ARTICLE; CALCULATION; CRYSTAL STRUCTURE; DEVICE; ELECTROCHEMISTRY; FILM; MOLECULAR ORBITAL CALCULATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SEMICONDUCTOR; STRUCTURE ANALYSIS; SYNTHESIS; X RAY ANALYSIS;

EID: 9344220522     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0484597     Document Type: Article

References (61)

1. (a) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99-117.
2. (b) Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim. Germany, 1999.
3. (a) Blanchet, G.; Rogers, J. J. Imaging Sci. Technol. 2003, 47, 296-303.
4. (b) Blanchet, G. B.; Loo, Y.-L..; Rogers, J. A.; Gao, F.; Fincher, C. R. Appl. Phys. Lett. 2003, 82, 463-465.
5. (a) Karl, N. Synth. Met. 2003, 133-134, 649-657.
6. (b) Campbell, I. H.; Smith, D. L. Int. J. High Speed Electron. Syst. 2001, 11, 585-615.
7. (a) Campbell, R. B.; Robertson, J. M.; Trotter, S. Acta Crystallogr. 1961, 14, 705-711.
8. (b) Lin, Y. Y.; Gundlach, D. J.; Nelson, S. F.; Jackson, T. N. IEEE Electron Device Lett. 1997, 18, 606-608.
9. (c) Butko, V. Y.; Chi, X.; Lang, D. V.; Ramirez, A. P. Appl. Phys. Lett. 2003, 83, 4773-4775.
10. (d) Meng, H.; Bendikov, M.; Mitchell, G.; Helgeson, R.; Wudl, F.; Bao, Z.; Siegrist, T.; Kloc, C.; Chem, C.-H. Adv. Mater. 2003, 15, 1090-1093.
11. (e) Butko, V. Y.; Chi, X.; Ramirez, A. P. Solid State Commun. 2003, 128, 431-434.
12. Sirringhaus, H.; Brown, P. J.; Friend, R. H.; Nielsen, M. M.; Bechgaard, K.; Langeveld-Voss, B. M. W.; Spiering, A. J. H.; Janssen, R. A. J.; Meijer, E. W.; Herwig, P.; de Leeuw, D. M. Nature 1999, 401, 685-688.
13. Li, X.-C.; Sirringhaus, H.; Garnier, F.; Holmes, A. B.; Moratti, S. C.; Feeder, N.; Clegg, W.; Teat, S. J.; Friend, R. H. J. Am. Chem. Soc. 1998, 120, 2206-2207.
14. (a) Facchetti, A.; Yoon, M.-H.; Stern, C. L.; Katz, H. E.; Marks, T. J. Angew. Chem., Int. Ed. 2003, 42, 3900-3903.
15. (b) Facchetti, A.; Mushrush, M.; Katz, H. E.; Marks, T. J. Adv. Mater. 2003, 12, 33-38.
16. (c) Sakamoto, Y.; Komatsu, S.; Suzuki, T. J. Am. Chem. Soc. 2001, 123, 4643-4644.
17. (d) Yassar, A.; Demanze, F.; Jaafari, A.; El Idrissi, M.; Coupry, C. Adv. Funct. Mater. 2002, 12, 699-708.
18. 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 der Craats, A. M.; Warman, J. M.; Zuilhof, H.; Sudholter, E. J. R. J. Am. Chem. Soc. 2000, 122, 11057-11066.
19. Malenfant, P. R.; Dimitrakopoulos, C. D.; Gelorme, J. D.; Kosbar, L. L.; Graham, T. O.; Curioni, A.; Andreoni, W. Appl. Phys. Lett. 2002, 80, 2517-2519.
20. Pappenfus, T. M.; Chesterfield, R. J.; Frisbie, C. D.; Mann, K. R.; Casado, J.; Raff, J. D.; Miller, L. L. J. Am. Chem. Soc. 2002, 124, 4184-4185.
21. Chesterfield, R. J.; Newman, C. R.; Pappenfus, T. M.; Ewbank, P. C.; Haukaas, M. H.; Mann, K. R.; Miller, L. L.; Frisbie, C. D. Adv. Mater. 2003, 15, 1278-1282.
22. Haddon, R. C.; Chi, X.; Itkis, M. E.; Anthony, J. E.; Eaton, D. L.; Siegrist, T.; Mattheus, C. C.; Palstra, T. T. M. J. Phys. Chem. B 2002, 106, 8288-8292.
23. Klebe, G.; Graser, F.; Hadicke, E.; Berndt, J. Acta Crystallogr. 1989, B45, 69-77.
24. Cornil, J.; Beljonne, D.; Calbert, J.-P.; Bredas, J.-L. Adv. Mater. 2001, 13, 1053-1067.
25. Curtis, M. D.; Cao, J.; Kampf, J. W. J. Am. Chem Soc. 2004, 126, 4318-4328.
26. Pappenfus, T. M.; Raff, J. D.; Hukkanen, E. J.; Burney, J. R.; Casado, J.; Drew, S. M.; Miller, L. L.; Mann, K. R. J. Org. Chem. 2002, 67, 6015-6024.
27. Casado, J.; Miller, L. L.; Mann, K. R.; Pappenfus, T. M.; Higuchi, H.; Orti, E.; Milian, B.; Pou-Amerigo, R.; Hernandez, V.; Lopez Navarrete, J. T. J. Am. Chem. Soc. 2002, 124, 12380-12388.
28. Higuchi, H.; Nakayama, T.; Koyama, H.; Ojima, J.; Wada, T.; Sasabe, H. Bull. Chem. Soc. Jpn. 1995, 68, 2363-2377.
29. Graf, D. D.; Duan, R. G.; Campbell, J. P.; Miller, L. L.; Mann, K. R. J. Am. Chem. Soc. 1997, 119, 5888-5899.
30. Bidan, G.; De Nicola, A.; Enee, V.; Guillerez, S. Chem. Mater. 1998, 10, 1052-1058.
31. Gallazzi, M. C.; Castellani, L.; Zerbi, G.; Sozzani, P. Synth. Met. 1991, 41, 495-498.
32. Barbarella, G.; Bongini, A.; Zambianchi, M. Macromolecules 1994, 27, 3039-3045.
33. Azumi, R.; Götz, G.; Debaerdemaeker, T.; Bäuerle, P. Chem.-Eur. J. 2000, 6, 735-744.
34. Kokubo, H.; Yamamoto, T. Macromol. Chem. Phys. 2001, 202, 1031-1034.
35. Higuchi, H.; Yoshida, S.; Uraki, Y.; Ojima, J. Bull. Chem. Soc. Jpn. 1998, 71, 2229-2237.
36. Yui, K.; Aso, Y.; Otsubo, T.; Ogura, F. Bull. Chem. Soc. Jpn. 1989, 62, 1539-1546.
37. (a) Sheldrick, G. SADABS v.2.03; 2002.
38. (b) Blessing, R. Acta Crystallogr. 1995, A51, 33-38.
39. SHELXL v.6.1; Bruker AXS, Madison. WI, 2001.
40. New software for searching the Cambridge Structural Database and visualizing crystal structures. Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M. K.; Macrae, C. F.; McCabe, P.; Pearson, J.; Taylor, R. Acta Crystallogr. 2002, B58, 389-397.
41. 2 v3.O software; Molecular Simulations Inc., San Diego, CA.
42. Kitaigorodskii, A. I. Organic Chemical Crystallography, Consultants Bureau Enterprises: New York, 1961.
43. (a) Ridley, J.; Zerner, M. C. Theor. Chim. Acta 1973, 32, 111-134.
44. (b) Zerner, M. C.; Loew, G. H.; Kichner, R. F.; Mueller-Westerhoff, U. T. J. Am. Chem. Soc. 1980, 102, 589-599.
45. Cornil, J.; Calbert, J. P.; Brédas, J. L. J. Am. Chem. Soc. 2001, 123, 1250-1251.
46. Newton, M. D. Int. J. Quantum Chem. 2000, 77, 255-263.
47. 2 software and the CIF files for BDT (CCDC data code NOBJET) and C5PTCDI (CCDC data code DICMUX).
48. Desiraju, G. R.; Gavezotti, A. Acta Crystallogr. 1989, B45, 473-482.
49. Barclay, T. M.; Cordes, A. W.; MacKinnon, C. D.; Oakley, R. T. Reed, R. W. Chem. Mater. 1997, 9, 981-990.
50. Barbarella, G.; Ostoja, P.; Maccagnani, P.; Pudova, O.; Antolini, L.; Casarini, D.; Bongini, A. Chem. Mater. 1998, 10, 3683-3689.
51. Bader, M. M.; Custelcean, R.; Ward, M. D. Chem. Mater. 2003, 15, 616-618.
52. Pappenfus, T. M.; Burand, M. W.; Janzen, D. E.; Mann, K. R. Org. Lett. 2003, 5, 1535-1538.
53. Minxie, Q.; Heng, F.; Yong, C. Jiegou Huaxue (Chinese J. Struct. Chem.) 1986, 159.
54. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed.; Wiley: New York, 1988.
55. (a) Reddy, D. S.; Ovchinnikov, Y. E.; Shishkin, O. V.; Struchkov, Y. T.; Desiraju, G. R. J. Am. Chem. Soc. 1996, 118, 4085-4089.
56. (b) Cordes, A. W.; Haddon, R. C.; Hicks, R. G.; Oakley, R. T.; Palstra, T. T. M. Inorg. Chem. 1992, 31, 1802-1808.
57. (c) Cordes, A. W.; Haddon, R. C.; Hicks, R. G.; Kennepohl, D. K.; Oakley, R. T.; Palstra, T. T. M.; Schneemeyer, L. F.; Scott, S. R.; Waszczak, J. V. Chem. Mater. 1993, 5, 820-825.
58. Kazmaier, P. M.; Huffman, R. J. Am. Chem. Soc. 1994, 116, 9684-9691.
59. Brédas, J.-L.; Calbert, J. P.; da Silva Filho, D. A.; Cornil, J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5804-5809.
60. Cornil, J.; Calbert, J. P.; Beljonne, D.; Silbey, R.; Brédas, J.-L. Adv. Mater. 2000, 12, 978-983.
61. Senthilkumar, K.; Grozema, F. C.; Bickelhaupl, F. M.; Siebbeles, L. D. A. J. Chem. Phys. 2003, 119, 9809-9817.