Theoretical calculations of band gaps in the aromatic structures of polythieno[3,4-b]benzene and polythieno[3,4-b]pyrazine

Journal of Physical Chemistry A

Volumn 104, Issue 30, 2000, Pages 7106-7112

  Kwon, Ohyun ^a   McKee, Michael L ^a  

^a AUBURN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; EXTRAPOLATION; MOLECULAR STRUCTURE; OLIGOMERS; PROBABILITY DENSITY FUNCTION;

POLYTHIENO BENZENE; POLYTHIENO PYRAZINE;

AROMATIC POLYMERS;

EID: 0034250619     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp000434g     Document Type: Article

References (77)

1. Handbook of Conducting Polymers; Skotheim, T. A., Elsenbaumer, R. L., Eds.; Marcel Dekker: New York, 1998.
2. (a) Schopf, G.; Koßmehl, G. Polythiophenes - Electrically Conductive Polymers; Sprincer-Verlag: New York, 1997.
3. (b) Handbook of Oligoand Polythiophenes; Fichou, D., Ed.; Wiley-VCH: New York, 1999.
4. See contributed chapters: Conjugated Oligomers, Polymers, and Dendrimers: From Polyacetylene to DNA. Proceedings of the Fourth Francqui Colloquium, Brussels, October 21-23, 1998; Brédas, J.-L., Ed.; DeBoeck Université: Paris, 1999.
5. Kobayashi, M.; Chen, J.; Chung, T.-C.; Moraes, F.; Heeger, A. J.; Wudl, F. Synth. Met. 1984, 9, 77.
6. Chung, T.-C.; Kaufman, J. H.; Heeger, A. J.; Wudl, F. Phys. Rev. B 1984, 30, 702.
7. Photonic and Optoelectronic Polymers; Jenekhe, S. A., Wynne, K. J., Eds.; ACS Symposium Series 672; American Chemical Society; Washington, DC, 1997.
8. Electronic Materials: The Oligomer Approach; Müllen, K., Wegner, G., Eds.; Wiley-VCH: Weinheim, 1998.
9. Yong, C.; Renyuan, R. Solid State Commun. 1985, 54, 211.
10. Prasad, P. N.; Swiatkiewicz, J.; Pfleger, J. Mol. Cryst. Liq. Cryst. 1988, 160, 53.
11. Sugiyama, T.; Wada, T.; Sasabe, H. Synth. Met. 1989, 28, C323.
12. Cava, M. P.; Lakshhmikantham, M. V. Acc. Chem. Res. 1975, 8, 139.
13. Wudl, F.; Kobayashi, M.; Heeger, A. J. J. Org. Chem. 1984, 49, 3382.
14. Kobayashi, M.; Colaneri, N.; Boysel, M.; Wudl, F.; Heeger, A. J. J. Chem. Phys. 1985, 82, 5717.
15. Lazzaroni, R.; Riga, J.; Verbist, J.; Brédas, J. L.; Wudl, F. J. Chem. Phys. 1988, 88, 4257.
16. Poplawski, J.; Ehrenfreund, E.; Schaffer, H.; Wudl, F.; Heeger, A. J. Synth. Met. 1989, 28, C539.
17. Brédas, J. L.; Thémans, B.; Fripiat, J. G.; André, J. M.; Chance, R. R. Phys. Rev. B 1984, 29, 6761.
18. Brédas, J. L.; Chance, R. R.; Silbey, R. Phys. Rev. B 1982, 26, 5843.
19. (a) Brédas, J. L.; Heeger, A. L.; Wudl, F. J. Chem. Phys. 1986, 85, 4673.
20. (b) Brédas, J. L J. Chem. Phys. 1985, 82, 3808.
21. Geisselbrecht, J.; Kurti, J.; Kuzmany, H. Synth. Met. 1993, 55-57, 4266.
22. Kiebooms, R.; Hoogmartens, I.; Adriaensens, P.; Vanderzande, D.; Gelan, J. Macromolecules 1995, 28, 4961.
23. Zerbi, G.; Magnoni, M. C.; Hoogmartens, I.; Kiebooms, R.; Carleer, R.; Vanderzande, D.; Gelan, J. Adv. Mater. 1995, 7, 1027.
24. Chen, S.-A.; Lee, C.-C. Pure. Appl. Chem. 1995, 67, 1983.
25. Chen, S.-A.; Lee, C.-C. Polymer 1996, 37, 519.
26. Paulussen, H.; Ottenbourgs, B.; Vanderzande, D.; Adriaensens, P.; Gelan, J. Polymer 1997, 38, 5221.
27. Lee, Y. S.; Kertesz, M. Int. J. Quantum Chem., Quantum Chem. Symp. 1987, 21, 163.
28. Lee, Y.-S.; Kertesz, M. J. Chem. Phys. 1988, 88, 2609.
29. Nayak, K.; Marynick, D. S. Macromolecules 1990, 23, 2237.
30. Lee, Y.-S.; Kertesz, M.; Elsenbaumer, R. Chem. Mater. 1990, 2, 526.
31. Kürti, J.; Surján, P. R. J. Chem. Phys. 1990, 92, 3247.
32. Karpfen, A.; Kertesz, M. J. Phys. Chem. 1991, 95, 7680.
33. Hoogmartens, I.; Adriaensens, P.; Vanderzande, D.; Gelan, J.; Quattrocchi, C.; Lazzaroni, R.; Brédas, J. L. Macromolecules 1992, 25, 7347.
34. Hong, S. Y.; Marynick, D. S. Macromolecules 1992, 25, 4652.
35. Quattrocchi, C.; Lazzaroni, R.; Brédas, J. L.; Kiebooms, R.; Vanderzande, D.; Gelan, J.; Meervelt. L. V. J. Phys. Chem. 1995, 99, 3932.
36. Cuff, L.; Kertesz, M. J. Chem. Phys. 1997, 106, 5541.
37. Viruela, P. M.; Viruela, R.; Ortí, E.; Brédas, J. L. J. Am. Chem. Soc. 1997, 119, 1360.
38. Brocks, G. J. Phys. Chem. 1996, 100, 17327.
39. Otto, P.; Ladik, J. Synth. Met. 1990, 36, 327.
40. Pomerantz, M.; Chaloner-Gill, B.; Harding, L. O.; Tseng, J. J.; Pomerantz, W. J. Chem. Commun. 1992, 1672.
41. Pomerantz, M.; Chaloner-Gill, B.; Harding, L. O.; Tseng, J. J.; Pomerantz, W. J. Synth. Met. 1993, 55, 960.
42. Kastner, J.; Kuzmany, H.; Vegh, D.; Landl, M.; Cuff, L.; Kertesz, M. Macromolecules 1995, 28, 2922.
43. Akoudad, S.; Roncali, J. Chem. Commun. 1998, 2081.
44. Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
45. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
46. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
47. Gross, E. K. U.; Kohn, W. Adv. Quantum Chem. 1990, 21, 255.
48. Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1998, 250, 454.
49. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439.
50. Wiberg, K. B.; Stratmann, R. E.; Frisch, M. J. Chem. Phys. Lett. 1998, 297, 60.
51. Foresman, J. B.; Head-Gordon, M.; Pople, J. A.; Frisch, M. J. J. Phys. Chem. 1992, 96, 135.
52. (a) Salzner, U.; Lagowski, J. B.; Pickup, P. G.; Poirier, R. A. J. Comput. Chem. 1997, 18, 1943.
53. (b) Salzner, U.; Pickup, P. G.; Poirier, R. A.; Lagowski, J. B. J. Phys. Chem. A 1998, 102, 2572.
54. Salzner, U.; Lagowski, J. B.; Pickup, P. G.; Poirier, R. A. Synth. Met. 1998, 96, 111.
55. Salzner, U. J. Mol. Model. 2000, 6, 195.
56. Savin, A.; Umrigar, C. J.; Gonze, X. Chem. Phys. Lett. 1998, 288, 391.
57. Salzner, U.; Kiziltepe, T. J. Org. Chem. 1999, 64, 764.
58. Salzner, U.; Lagowski, J. B.; Pickup, P. G.; Poirier, R. A. J. Org. Chem. 1999, 64, 7419.
59. Krzeminski, C.; Delerue, C.; Allan, G.; Haguet, V.; Stiévenard, D.; Frère, P.; Levillain, E.; Roncali, J. J. Chem. Phys. 1999, 111, 6643.
60. Stowasser, R.; Hoffmann, R. J. Am. Chem. Soc. 1999, 121, 3414.
61. Tozer, D. J.; Amos, R. D.; Handy, N. C.; Roos, B. O.; Serrano-Andrés, L. Mol. Phys. 1999, 97, 859.
62. Kwon, O.; McKee, M. L. J. Phys. Chem. B 2000, 104, 1686.
63. SPARTAN version 5.0, Wavefunction, Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92612.
64. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7; Gaussian, Inc.: Pittsburgh, PA, 1998.
65. Zerner, M. C.; Correa de Mello, P.; Hehenberger, M. Int. J. Quantum Chem. 1982, 21, 251.
66. (a) André, J.-M.; Delhalle, J.; Brédas, J. L. Quantum Chemistry Aided Design of Organic Polymers; World Scientific: River Edge, NJ, 1991.
67. (b) Roncali, J. Acc. Chem. Res. 2000, 33, 147.
68. Meier, H.; Stalmach, U.; Kolshorn, H. Acta Polym. 1997, 48, 379.
69. Hotta, S.; Waragai, K. J. Mater. Chem. 1991, 1, 835.
70. Horowitz, G.; Bachet, B.; Yassar, A.; Lang, P.; Demanze, F.; Fave, J.-L.; Garnier, F. Chem. Mater. 1995, 7, 1337.
71. Fichou, D.; Bachet, B.; Demanze, F.; Billy, I.; Horowitz, G.; Gamier, F. Adv. Mater. 1996, 8, 500.
72. Viruela, P. M.; Viruela, R.; Orti, E. Int. J. Quantum Chem. 1998, 70, 303.
73. Huheey, J. E.; Keiter, E. A.; Keiter, R. L. Inorganic Chemistry; HarperCollins College Publishers: New York, 1993.
74. DiCésare, N.; Belletête, M.; Marrano, C.; Leclerc, M.; Durocher, G. J. Phys. Chem. A 1998, 102, 5142.
75. Brédas, J. L.; Street, G. B.; Thémans, B.; André, J. M. J. Chem. Phys. 1985, 83, 1323.
76. Karelson, M.; Zerner, M. C. Chem. Phys. Lett. 1994, 224, 213.
77. When the geometry of TN3 was optimized at the AM1 level with two hexyl substituents per unit, the planar form was more stable than the nonplanar form.