Revised Structures of N-Substituted Dibrominated Pyrrole Derivatives and Their Polymeric Products. Termaleimide Models with Low Optical Band Gaps

Journal of Organic Chemistry

Volumn 63, Issue 8, 1998, Pages 2646-2655

  Choi, Dong Sook ^a   Huang, Shenlin ^a   Huang, Mingsheng ^a   Barnard, Thomas S ^a   Adams, Richard D ^a   Seminario, Jorge M ^a   Tour, James M ^a  

^a UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000318431     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9722055     Document Type: Article

References (33)

1. Street, G. B. In Handbook of Conducting Polymers; Skotheim, T. J., Ed.; Dekker: New York, 1986.
2. (b) Bureau, J. M.; Gazard, M.; Champagne, M.; Dubois, J. C.; Tourillon, G.; Gamier, F. Mol. Cryst. Liq. Cryst. 1985, 118, 235.
3. (c) Street, G. B.; Lindsey, S. E.; Nazzal, A. I.; Wynne, K. J. Mol. Cryst. Liq. Cryst. 1985, 118, 137.
4. Groenendaal, L.; Peerlings, H. W. I.; van Dongen, J. L. J.; Havinga, E. E.; Vekemans, J. A. J. M.; Meijer, E. W. Macromolecules 1995, 28, 116.
5. (b) Pomerantz, M.; Yang, H.; Cheng, Y. Macromolecules 1995, 28, 5706.
6. Brockmann, T. W.; Tour, J. M. J. Am. Chem. Soc. 1995, 117, 4437.
7. (b) Brockmann, T. W.; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 7435.
8. Beddoes, R. L.; Zhao, Y.; Joule, J. A. Acta Crystallogr. 1996, C52, 2313. This reference contains the corrected structure for the Diels-Alder adduct, confirmed by X-ray analysis, resulting from the [4 + 2] cycloaddition of 4a and cyclopentadiene; however, the structures suggested by Beddoes et al. for the NBS-bromination products of N-alkylpyrroles are incorrect.
9. Gilow, H. M.; Burton, D. E. J. Org. Chem. 1981, 46, 2221.
10. (b) Artico, M. In Heterocyclic Compounds, Pyrroles; Jones, R. A., Ed.; Wiley: New York, 1990; Vol. 48, Part I.
11. w = 0.043.
12. Tour, J. M. Chem. Rev. 1996, 96, 537.
13. Earl, R. A.; Clough, F. W.; Townsend, L. B. J. Heterocycl. Chem. 1978, 15, 1479.
14. (b) Brown, J. P. Chem. Abstr. 1966, 65, 2131a.
15. Sandosham, J. Undheim, K. Acta Chem. Scand. 1989, 43, 684.
16. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
17. (b) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478.
18. Khan, M. N. J. Chem. Soc., Perkin Trans. 2 1987, 819.
19. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.
20. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, 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.; Ciolowski, J.; Stefanov, B. B.; Nenayakkara, 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 E.1, Gaussian, Inc., Pittsburgh, PA, 1996.
21. (b) Hehre, J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory; Wiley: New York, 1986.
22. (c) Modern Density Functional Theory: A Tool for Chemistry; Seminario J. M., Politzer, P., Eds.; Elsevier: Amsterdam, 1995.
23. (d) Recent Developments and Applications of Modern Density Functional Theory; Seminario, J. M., Ed., Elsevier: Amsterdam, 1996.
24. Wang, N.; Teo, K.; Anderson, H. J. Can. J. Chem. 1977, 55, 4112.
25. Khoury, Y.; Kovacic, P.; Gilow, H. M. J. Polym. Sci., Polym. Lett. 1981, 19, 395.
26. Mehta, N. B.; Phillips, A. P.; Lui, F. F.; Brooks, R. E. J. Org. Chem. 1960, 25, 1012.
27. Sakata, Y. Yakugaku Zasshi 1962, 82, 929.
28. Scharf, H.-D.; Korte, F. Chem. Ber. 1965, 24, 764.
29. Balasubramaniyan, V.; Laddha, G. K.; Argade, N. P. Org. Prep. Proc. Intl. 1991, 23, 388.
30. (b) Martin, E. L.; Dickinson, C. L.; Roland, J. R. J. Org. Chem. 1961, 26, 2032.
31. Xie, G.; Lown, J. W. Tetrahedron Lett. 1994, 35, 5555.
32. Edge, S.; Charlton, A.; Hansen, T. K.; Varma, K. S. Underhill, A. E.; Kathirgamanathan, P.; Becher, J. Chem. Ind. 1991, 4, 130.
33. Felix, G.; Dunogues, J.; Pisciotti, F.; Calas, R. Angew. Chem., Int. Ed. Engl. 1977, 16, 488.