Geometric structure and torsional potential of biisothianaphthene. A comparative DFT and ab initio study

Journal of the American Chemical Society

Volumn 119, Issue 6, 1997, Pages 1360-1369

  Viruela, Pedro M ^a   Viruela, Rafael ^a   Ortí, Enrique ^a   Brédas, Jean Luc ^b  

^a UNIVERSITY OF VALENCIA   (Spain)

^b UNIVERSITY OF MONS   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BIISOTHIANAPHTHENE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; FOURIER TRANSFORMATION; MOLECULAR DYNAMICS; STEREOCHEMISTRY; THEORY;

EID: 0030901325     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961586l     Document Type: Article

References (105)

1. (a) Wudl, F.; Kobayashi, M.; Heeger, A. J. J. Org. Chem. 1984, 49, 3382.
2. (b) Chung, T. C.; Kaufman, J.; Heeger, A. J.; Wudl, F. Phys. Rev. B 1984, 30, 702.
3. (c) Kobayashi, M.; Colaneri, N.; Boysel, M.; Wudl, F.; Heeger, A. J. J. Chem. Phys. 1985, 82, 5717.
4. (d) Colaneri, N.; Kobayashi, M.; Heeger, A. J.; Wudl, F. Synth. Met. 1986, 14, 15.
5. (a) Brédas, J. L. J. Chem. Phys. 1985, 82, 3808.
6. (b) Brédas, J. L.; Thémans, B.; André, J. M.; Heeger, A. J.; Wudl, F. Synth. Met. 1985, 11, 343.
7. (c) Brédas, J. L.; Heeger, A. J.; Wudl, F. J. Chem. Phys. 1986, 85, 4673.
8. (d) Brédas, J. L. Synth. Met. 1987, 17, 115.
9. (a) Lee, Y. S.; Kertesz, M. J. Chem. Phys. 1988, 88, 2609.
10. (b) Kertesz, M.; Lee, Y. S. J. Phys. Chem. 1987, 91, 2690.
11. (c) Lee, Y. S.; Kertesz, M.; Elsenbaumer, R. L. Chem. Mater. 1990, 2, 526.
12. (d) Karpfen, A.; Kertesz, M. J. Phys. Chem. 1991, 95, 7680.
13. (e) Kürti, J.; Surján, P. R.; Kertesz, M. J. Am. Chem. Soc. 1991, 113, 9865.
14. (a) Toussaint, J. M.; Wudl. F.; Brédas, J. L. J. Chem. Phys. 1989, 91, 1783.
15. (b) Toussaint, J. M.; Brédas, J. L. J. Chem. Phys. 1991, 94, 8122.
16. (a) Bolognesi. A.; Catellani, M.; Destri, S.; Zamboni, R.; Taliani, C. J. Chem. Soc., Chem. Commum. 1988, 246.
17. (b) Taliani, C.; Ruani, G.; Zamboni, R.; Bolognesi, A.; Catellani, M.; Destri, S.; Porzio, W.; Ostoja, P. Synth. Met. 1989, 28, C507.
18. (c) Quattrocchi, C.; Lazzaroni, R.; Brédas, J. L.; Zamboni, R.; Taliani, C. Macromolecules 1993, 26, 1260.
19. (a) Hanack, M.; Mangold, K.-M.; Röhrig, U.; Maichle-Mössmer, C. Synth. Met. 1993, 60, 199.
20. (b) Hanack, M.; Schmid, U.; Röhrig, U.; Toussaint, J. M.; Adant, C.; Brédas, J. L. Chem. Ber. 1993, 126, 1487.
21. (a) Pomerantz, M.; Chaloner-Gill, B.; Harding, L. O.; Tseng, J.; Pomerantz, W. J. J. Chem. Soc., Chem. Commum. 1992, 1672.
22. (b) Quattrocchi, C.; Lazzaroni, R.; Kiebooms, R.; Vanderzande, D.; Gelan, J.; Brédas, J. L. Synth. Met. 1995, 69, 691.
23. (c) Kastner, J.; Kuzmany, H.; Vegh, D.; Landl, M.; Cuff, L.; Kertesz, M. Macromolecules 1995, 28, 2992.
24. Kürti, J.; Surján, P. R. J. Chem. Phys. 1990, 92, 3247.
25. (a) Faulques, E.; Wallnöfer, W.; Kuzmany, H. J. Chem. Phys. 1989, 90, 7585.
26. (b) Geisselbrecht, J.; Kürti, J.; Kuzmany, H. Synth. Met. 1993, 55-57, 4266.
27. Nayak, K.; Marynick, D. S. Macromolecules 1990, 23, 2237.
28. (a) Hoogmartens, I.; Adriaensens, P.; Carleer, R.; Vanderzande, D.; Martens, H.; Gelan, J. Synth. Met. 1992, 51, 219.
29. (b) Hoogmartens, I.; Adriaensens, P.; Vanderzande, D.; Gelan, J.; Quattrocchi, C.; Lazzaroni, R.; Brédas, J. L. Macromolecules 1992, 25, 7347.
30. (c) Kiebooms, R.; Hoogmartens, I.; Adriaensens, P.; Vanderzande, D.; Gelan, J. Macromolecules 1995, 28, 4961.
31. Zerbi, G.; Magnoni, M. C.; Hoogmartens, I.; Kiebooms, R.; Carleer, R.; Vanderzande, D.; Gelan, J. Adv. Mater. 1995, 7, 1027.
32. Brédas, J. L.; Chance, R. R.; Silbey, R.; Nicolas, G.; Durand, P. J. Chem. Phys. 1981, 75, 255; 1982, 77, 371.
33. Brédas, J. L.; Chance, R. R.; Silbey, R.; Nicolas, G.; Durand, P. J. Chem. Phys. 1981, 75, 255; 1982, 77, 371.
34. For a review of the experimental and theoretical studies on the conformational isomerism of 2,2′-bithiophene and other oligothiophenes see: (a) Ortí, E.; Viruela, P. M.; Sánchez-Marín, J.; Tomás, F. J. Phys. Chem. 1995, 99, 4955. (b) Hernández, V.; López-Navarrete, J. T. J. Chem. Phys. 1994, 101, 1369.
35. For a review of the experimental and theoretical studies on the conformational isomerism of 2,2′-bithiophene and other oligothiophenes see: (a) Ortí, E.; Viruela, P. M.; Sánchez-Marín, J.; Tomás, F. J. Phys. Chem. 1995, 99, 4955. (b) Hernández, V.; López-Navarrete, J. T. J. Chem. Phys. 1994, 101, 1369.
36. Quattrocchi, C.; Lazzaroni, R.; Brédas, J. L.; Kiebooms, R.; Vanderzande, D.; Gelan, J.; Van Meervelt, L. J. Phys. Chem. 1995, 99, 3932.
37. Following IUPAC nomenclature the isothianaphthene moiety has to be numbered starting from the carbon contiguous to the sulfur atom and assigning number 2 to the sulfur. The IUPAC name for biisothianaphthene therefore is 1,1′-biisothianaphthene. Unlike isothianaphthene, the numbering of thiophene starts with the sulfur atom and the dimer is named 2,2′-bithiophene. The numbering displayed in Figure 1 for the isothianaphthene moieties follows the sequence used for thiophene and has been defined to facilitate the comparison in the text between thiophene and isothianaphthene monomers and dimers.
38. (a) Visser, G. J.; Heeres, G. J.; Wolters, J.; Vos, A. Acta Crystallogr., B 1968, 24, 467.
39. (b) Chaloner, P. A.; Gunatunga, S. R.; Hitchcock, P. B. Acta Crystallogr., C 1994, 50, 1941.
40. (c) Pelletier, M.; Brisse, F. Acta Crystallogr., C 1994, 50, 1942.
41. (d) Pyrka, G, J.; Fernando, Q. Acta Crystallogr., C 1988, 44, 562.
42. (a) Hernández, V.; López-Navarrete, J. T. Synth. Met. 1992, 51, 211.
43. (b) Belletête, M.; Leclerc, M.; Durocher, G. J. Phys. Chem. 1994, 98, 9450.
44. (a) Parr, R. G.; Yang, W. Density-Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
45. (b) Levy, M. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 6062.
46. (c) Ziegler, T. Chem. Rev. 1991, 91, 651.
47. (d) Jones, R. O.; Gunnarsson, O. Rev. Mod. Phys. 1990, 61, 689.
48. For a discussion of the scaling properties of several methods, see, for example, the following: (a) Scuseria, G. E.; Lee, T. J. J. Chem. Phys. 1990, 93, 5851. (b) Strout, D. L.; Scuseria, G. E. J. Chem. Phys. 1995, 102, 8448. (c) Foresman, J. B.; Frisch, Æ. Exploring Chemistry with Electronic Structure Methods: A Guide to Using Gaussian; Gaussian Inc.: Pittsburgh, PA, 1993.
49. For a discussion of the scaling properties of several methods, see, for example, the following: (a) Scuseria, G. E.; Lee, T. J. J. Chem. Phys. 1990, 93, 5851. (b) Strout, D. L.; Scuseria, G. E. J. Chem. Phys. 1995, 102, 8448. (c) Foresman, J. B.; Frisch, Æ. Exploring Chemistry with Electronic Structure Methods: A Guide to Using Gaussian; Gaussian Inc.: Pittsburgh, PA, 1993.
50. For a discussion of the scaling properties of several methods, see, for example, the following: (a) Scuseria, G. E.; Lee, T. J. J. Chem. Phys. 1990, 93, 5851. (b) Strout, D. L.; Scuseria, G. E. J. Chem. Phys. 1995, 102, 8448. (c) Foresman, J. B.; Frisch, Æ. Exploring Chemistry with Electronic Structure Methods: A Guide to Using Gaussian; Gaussian Inc.: Pittsburgh, PA, 1993.
51. (a) Wimmer, E.; Andzelm, J. J. Chem. Phys. 1992, 96, 1280.
52. (b) Becke, A. D. J. Chem. Phys. 1988, 88, 2547.
53. (a) Andzelm, J.; Sosa, C.; Eades, R. A. J. Phys. Chem. 1993, 97, 4664.
54. (b) Sosa, C.; Andzelm, J.; Lee, C.; Blake, J. F.; Chenard, B. L.; Butler, T. W. Int. J. Quantum Chem. 1994, 49, 511.
55. (c) Sosa, C.; Lee, C. J. Chem. Phys. 1993, 98, 8004.
56. (a) Langreth, D. C.; Perdew, J. P. Phys. Rev. B 1980, 21, 5469.
57. (b) Becke, A. D. Int. J. Quantum Chem. 1983, 27, 1915.
58. (c) Perdew, J. P. Phys. Rev. Lett. 1985, 55, 1655.
59. (d) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
60. (e) Perdew, J. P. Physica B 1991, 172, 1.
61. (f) Wang, Y.; Perdew, J. P. Phys. Rev. B 1991, 44, 13298.
62. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Wong, M. W.; Johnson, B. G.; Wong, M. W.; Foresman, J. B.; Robb. M. A.; Head-Gordon, M.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; DeFrees, D. J.; Baker, J.; Stewart, J. J. P.; Pople, J. A. Gaussian 92/DFT, Revision G.3; Gaussian Inc.: Pittsburgh, PA, 1993.
63. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gil, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision B.1; Gaussian Inc.: Pittsburgh PA, 1995.
64. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 16, 217.
65. Møller, C.; Plesset, M. S. Phys. Rev. 1934, 46, 618.
66. (a) Binkley, J. S.; Pople, J. A. Int. J. Quantum Chem. 1975, 9, 229.
67. (b) Pople, J. A.; Binkley, J. S.; Seeger, R. Int. J. Quantum Chem. Symp. 1976, 10, 1.
68. (c) Krishnan, R.; Pople, J. A. Int. J. Quantum Chem. 1978, 14, 91.
69. (d) Krishnan, R.; Frisch, M. J.; Pople, J. A. J. Chem. Phys. 1980, 72, 4244.
70. (a) Hohenberg, P.; Kohn, W. Phys. Rev. B 1964, 136, 864.
71. (b) Kohn, W.; Sham. L. Phys. Rev. A 1965, 140, 1133.
72. (a) Dirac, P. A. M. Proc. Cambridge Philos. Soc. 1930, 26, 376.
73. (b) Slater, J. C. The Self-Consistent Field for Molecules and Solids; Quantum Theory of Molecules and Solids; McGraw-Hill: New York, 1974; Vol 4.
74. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
75. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
76. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1993, 37, 785.
77. VWN See the following: (a) Gaussian/DFT supplement manual. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372; 98, 5648. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 1623.
78. VWN See the following: (a) Gaussian/DFT supplement manual. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372; 98, 5648. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 1623.
79. VWN See the following: (a) Gaussian/DFT supplement manual. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372; 98, 5648. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 1623.
80. VWN See the following: (a) Gaussian/DFT supplement manual. (b) Becke, A. D. J. Chem. Phys. 1993, 98, 1372; 98, 5648. (c) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 1623.
81. Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
82. Perdew, J. P.; Wang, Y. Phys. Rev. B 1992, 45, 13244.
83. Novoa, J. J.; Sosa, C. J. Phys. Chem. 1995, 99, 15837.
84. Schlegel, H. B. J. Comput. Chem. 1982, 3, 214.
85. Bak, B.; Christensen, D.; Hansen-Nygaard, L.; Rastrup-Andersen, J. J. Mol. Spectrosc. 1961, 7, 58.
86. Charbonneau, G.; Delugeard, V. Acta Crystallogr., B 1976, 32, 1420.
87. Baughman, R. H.; Kohler, B. E.; Levy, I. J.; Spangler C. Synth. Met. 1985, 11, 37.
88. (a) Bolhuis, F. V.; Wynberg, H.; Havinga, E. E.; Meijer, E. W.; Staring, E. G. J. Synth. Met. 1989, 30, 381.
89. (b) DeWitt, L.; Blanchard, G. J.; LeGoff, E.; Benz, M. E.; Liao, J. H.; Kanatzidis, M. G. J. Am. Chem. Soc. 1993, 115, 12158.
90. (c) Barbarella, G.; Zambianchi, M.; Bongini, A.; Antolini, L. Adv. Mater. 1994, 6, 561.
91. (d) Barbarella, G.; Zambianchi, M.; Bongini, A.; Antolini, L. Adv. Mater. 1992, 4, 282.
92. (e) Hotta, S.; Waragai, K. J. J. Mater. Chem. 1991, 1, 835.
93. (f) Barbarella, G.; Zambianchi, M.; Bongini, A.; Antolini, L. Adv. Mater. 1993, 5, 834.
94. (g) Liao, J.-H.; Benz, M.; LeGoff, E.; Kanatzidis, M. G. Adv. Mater. 1994, 6, 135.
95. Samdal, S.; Samuelsen, E. J.; Volden, H. V. Synth. Met. 1993, 59, 259.
96. (a) Khetrapal, C. L.; Kunwar, A. C. Mol. Phys. 1974, 28, 441.
97. (b) Bucci, P.; Longeri, M.; Veracini, C. A.; Lunazzi, L. J. Am. Chem. Soc. 1974, 96, 1305.
98. (c) Ter Beek, L. C.; Zimmerman, D. S.; Burnell, E. E. Mol. Phys. 1991, 74, 1027.
99. (a) Rubio, M.; Merchán, M.; Ortí, E.; Roos, B. O. J. Chem. Phys. 1995, 102, 3580.
100. (b) Rubio, M.; Merchán, M.; Ortí, E.; Roos, B. O. Chem. Phys. Lett. 1996, 248, 321.
101. Dewar, M. J. S.; Thiel, W. J. Am. Chem. Soc. 1977, 99, 4899.
102. Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902.
103. Stewart, J. J. P. J. Comput. Chem. 1989, 10, 209, 221.
104. (a) López-Navarrete, J. T.; Tian, B.; Zerbi, G. Synth. Met. 1990, 38, 299.
105. (b) Alemán, C.; Julia, L. J. Phys. Chem. 1996, 100, 1524.