Biphenylene dimer. Molecular fragment of a two-dimensional carbon net and double-stranded polymer

Journal of the American Chemical Society

Volumn 118, Issue 31, 1996, Pages 7272-7279

  Rajca, Andrzej ^a   Safronov, Andrej ^a   Rajca, Suchada ^a   Ross II, Charles R ^a   Stezowski, John J ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; THEORY; X RAY CRYSTALLOGRAPHY;

EID: 0029739928     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961065y     Document Type: Article

References (92)

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25. Leading references for linear and angular oligophenylenes: (a) Barton, J. W.; Walker, R. B. Tetrahedron Lett. 1978, 1005. (b) Barton, J. W.; Rowe, D. J. Tetrahedron Lett. 1983, 299. (c) Berris, B. C.; Hovakeemian, G. H.; Lai, Y.-H.; Mestdagh, H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1985, 107, 5670. (d) Diercks, R.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1986, 108, 3150. (e) Blanco, L.; Helson, H. E.; Hirthammer, M.; Mestdagh, H.; Spyroudis, S.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1987, 26, 1246. (f) Schmidt-Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1992, 114, 9713. (g) Boese, R.; Matzger, A. J.; Mohler, D. L.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1478.
26. Leading references for linear and angular oligophenylenes: (a) Barton, J. W.; Walker, R. B. Tetrahedron Lett. 1978, 1005. (b) Barton, J. W.; Rowe, D. J. Tetrahedron Lett. 1983, 299. (c) Berris, B. C.; Hovakeemian, G. H.; Lai, Y.-H.; Mestdagh, H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1985, 107, 5670. (d) Diercks, R.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1986, 108, 3150. (e) Blanco, L.; Helson, H. E.; Hirthammer, M.; Mestdagh, H.; Spyroudis, S.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1987, 26, 1246. (f) Schmidt-Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1992, 114, 9713. (g) Boese, R.; Matzger, A. J.; Mohler, D. L.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1478.
27. Leading references for linear and angular oligophenylenes: (a) Barton, J. W.; Walker, R. B. Tetrahedron Lett. 1978, 1005. (b) Barton, J. W.; Rowe, D. J. Tetrahedron Lett. 1983, 299. (c) Berris, B. C.; Hovakeemian, G. H.; Lai, Y.-H.; Mestdagh, H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1985, 107, 5670. (d) Diercks, R.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1986, 108, 3150. (e) Blanco, L.; Helson, H. E.; Hirthammer, M.; Mestdagh, H.; Spyroudis, S.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1987, 26, 1246. (f) Schmidt-Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1992, 114, 9713. (g) Boese, R.; Matzger, A. J.; Mohler, D. L.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1478.
28. Leading references for linear and angular oligophenylenes: (a) Barton, J. W.; Walker, R. B. Tetrahedron Lett. 1978, 1005. (b) Barton, J. W.; Rowe, D. J. Tetrahedron Lett. 1983, 299. (c) Berris, B. C.; Hovakeemian, G. H.; Lai, Y.-H.; Mestdagh, H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1985, 107, 5670. (d) Diercks, R.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1986, 108, 3150. (e) Blanco, L.; Helson, H. E.; Hirthammer, M.; Mestdagh, H.; Spyroudis, S.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1987, 26, 1246. (f) Schmidt-Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1992, 114, 9713. (g) Boese, R.; Matzger, A. J.; Mohler, D. L.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1478.
29. Leading references for linear and angular oligophenylenes: (a) Barton, J. W.; Walker, R. B. Tetrahedron Lett. 1978, 1005. (b) Barton, J. W.; Rowe, D. J. Tetrahedron Lett. 1983, 299. (c) Berris, B. C.; Hovakeemian, G. H.; Lai, Y.-H.; Mestdagh, H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1985, 107, 5670. (d) Diercks, R.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1986, 108, 3150. (e) Blanco, L.; Helson, H. E.; Hirthammer, M.; Mestdagh, H.; Spyroudis, S.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1987, 26, 1246. (f) Schmidt-Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1992, 114, 9713. (g) Boese, R.; Matzger, A. J.; Mohler, D. L.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1478.
30. Leading references for linear and angular oligophenylenes: (a) Barton, J. W.; Walker, R. B. Tetrahedron Lett. 1978, 1005. (b) Barton, J. W.; Rowe, D. J. Tetrahedron Lett. 1983, 299. (c) Berris, B. C.; Hovakeemian, G. H.; Lai, Y.-H.; Mestdagh, H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1985, 107, 5670. (d) Diercks, R.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1986, 108, 3150. (e) Blanco, L.; Helson, H. E.; Hirthammer, M.; Mestdagh, H.; Spyroudis, S.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1987, 26, 1246. (f) Schmidt-Radde, R. H.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1992, 114, 9713. (g) Boese, R.; Matzger, A. J.; Mohler, D. L.; Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1995, 34, 1478.
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40. (b) A large DOS at the Fermi level, such as associated with narrow and partially-filled bands, is also relevant to magnetism; for a review on organic high-spin polyradicals, exhibiting near-degeneracies at the HOMO level, see: Rajca, A. Chem. Rev. 1994, 94, 871. Band structure calculations at the EHT level for model polymeric polyradicals: Yoshizawa, K.; Hoffmann, R. Chem. Eur. 1995, 1, 403.
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44. f° for biphenylene at the 6-31G*(RMP2-FC)//6-31G* level of theory is 99.8 kcal/ mol; see: Schulman, J. M.; Disch, R. L. J. Mol. Struct.: THEOCHEM 1992, 259, 173.
45. f° for biphenylene at the 6-31G*(RMP2-FC)//6-31G* level of theory is 99.8 kcal/ mol; see: Schulman, J. M.; Disch, R. L. J. Mol. Struct.: THEOCHEM 1992, 259, 173.
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