Are N,N-dihydrodiazatetracene derivatives antiaromatic?

Journal of the American Chemical Society

Volumn 130, Issue 23, 2008, Pages 7339-7344

  Miao, Shaobin ^a   Brombosz, Scott M ^a   Schleyer, Paul V R ^b   Wu, Judy I ^b   Barlow, Stephen ^a   Marder, Seth R ^a   Hardcastle, Kenneth I ^c   Bunz, Uwe H F ^a  

^a GEORGIA INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF GEORGIA   (United States)

^c EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; AROMATIZATION; BIOELECTRIC PHENOMENA; VOLTAMMETRY;

AMERICAN CHEMICAL SOCIETY (ACS); AROMATICITY; COMPUTATIONAL RESULTS; ELECTRON SYSTEMS; HETEROACENES; NUCLEUS INDEPENDENT CHEMICAL SHIFT (NICS); PLANARITY; RADICAL ANIONS; SYNTHESIS (OF CHIRAL IONIC LIQUIDS); X RAY CHARACTERIZATION;

CYCLIC VOLTAMMETRY;

ANION; AROMATIC COMPOUND; N,N DIHYDRODIAZATETRACENE;

ARTICLE; CYCLIC POTENTIOMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 44949233322     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077614p     Document Type: Article

References (48)

1. Nelson, S. F.; Lin, Y. Y.; Gundlach, D. J.; Jackson, T. N. Appl. Phys. Lett. 1998, 72, 1854-1856.
2. (a) Dimitrakopoulos, C. D.; Malenfant, P. R. L. Adv. Mater. 2002, 14, 99-117.
3. (b) Dimitrakopoulos, C. D.; Mascara, D. J. IBM J. Res. Develpment 2001, 45, 11-27.
4. (c) Reese, C.; Bao, Z. N. J. Mater. Chem. 2006, 16, 329-333.
5. (d) Roberson, L. B.; Kowalik, J.; Tolbert, L. M.; Kloc, C.; Zeis, R.; Chi, X. L.; Fleming, R.; Wilkins, C. J. Am. Chem. Soc. 2005, 127, 3069-3075.
6. (a) Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048.
7. (b) Anthony, J. E.; Brooks, J. S.; Eaton, D. L.; Parkin, S. R. J. Am. Chem. Soc. 2001, 123, 9482-9483.
8. (c) Payne, M. M.; Parkin, S. R.; Anthony, J. E. J. Am. Chem. Soc. 2005, 127, 8028-8029.
9. (d) Payne, M. M.; Delcamp, J. H.; Parkin, S. R.; Anthony, J. E. Org. Lett. 2004, 6, 1609-1612.
10. Anthony, J. E.; Eaton, D. L.; Parkin, S. R. Org. Lett. 2002, 4, 15-18.
11. (a) Fischer, O.; Hepp, E. Chem. Ber. 1890, 23, 2789-2798.
12. (b) Fischer, O.; Hepp, E. Chem. Ber. 1900, 33, 1485-1498.
13. (c) Kehrmann, F. Chem. Ber. 1890, 23, 2446-2454.
14. Winkler, M.; Houk, K. N. J. Am. Chem. Soc. 2007, 129, 1805-1815.
15. Wudl, F.; Koutenis, P. A.; Weitz, A.; Ma, B.; Strassner, T.; Houk, K. N.; Khan, S. I. Pure Appl. Chem. 1999, 71, 295-302.
16. Miao, Q.; Nguyen, T. Q.; Someya, T.; Blanchet, G. B.; Nuckolls, C. J. Am. Chem. Soc. 2003, 125, 10284-10287.
17. Tadokoro, M.; Yasuzuka, S.; Nakamura, M.; Shinoda, T.; Tatenuma, T.; Mitsumi, M.; Ozawa, Y.; Toriumi, K.; Yoshino, H.; Shiomi, D.; Sato, K.; Takui, T.; Mori, T.; Murata, K. Angew. Chem., Int. Ed. 2006, 45, 5144-5147.
18. Jenekhe, S. A. Macromolecules 1991, 24, 1-10.
19. Nishida, J.; Naraso; Murai, S.; Fujiwara, E.; Tada, H.; Tomura, M.; Yamashita, Y. Org. Lett. 2004, 6, 2007-2010.
20. Hinsberg, O. Liebigs Ann. Chem. 1901, 319, 257-286.
21. Breslow, R.; Brown, J.; Gajewski, J. J. J. Am. Chem. Soc. 1967, 89, 4383-4390.
22. Cava, M. P.; Schlessinger, R. H. Tetrahedron Lett. 1964, 3815-3817.
23. Miao, S.; Smith, M. D.; Bunz, U. H. F. Org. Lett. 2006, 8, 757-760.
24. (b) Miao, S.; Schleyer, P. v. R.; Wu, J. I.; Hardcastle, K. I.; Bunz, U. H. F. Org. Lett. 2007, 9, 1073-1076.
25. (a) Odom, S. A.; Parkin, S. R.; Anthony, J. E. Org. Lett. 2003, 5, 4245-4248.
26. (b) Anthony J. E. In Functional Organic Materials; Bunz, U. H. F., Müller, T. J. J., Eds.; Wiley-VCH: Weinheim, 2007; pp 511-545.
27. Holmes, D.; Kumaraswamy, S.; Matzger, A. J.; Vollhardt, K. P. C. Chem. Eur. J. 1999, 5, 3399-3412.
28. Perkampus H.-H. UV-Vis Atlas of Organic Compounds, 2nd ed.; VCH: Weinheim, 1992.
29. +/0 reduction wave corresponds to more than one electron. This may suggest coupled electron and proton transfer processes as have been seen for other phenazine derivatives; however, we have not investigated this aspect in detail.
30. (b) Laviron, E.; Roullier, L. J. Electroanal. Chem. 1983, 157, 7-18.
31. (c) Sawyer, D. T.; Komai, R. Y. Anal. Chem. 1972, 44, 715-721.
32. (a) These estimates were made as previously described using Alq3 and TPD as references for EA and IP, respectively. As discussed, alternative less conservative (more exothermic) estimates of EA can be obtained using other comparisons.
33. (b) Zhan, X.; Risko, C.; Amy, F.; Chan, C.; Zhao, W.; Barlow, S.; Kahn, A.; Brédas, J. L.; Marder, S. R. J. Am. Chem. Soc. 2005, 127, 9021-9029.
34. (c) An, Z.; Yu, J.; Jones, S. C.; Barlow, S.; Yoo, S.; Domercq, B.; Prins, P.; Siebbeles, L. D. A.; Kippelen, B.; Marder, S. R. Adv. Mater. 2005, 17, 2580-2583.
35. (d) Cahen, D.; Kahn, A. Adv. Mater. 2003, 15, 271-277.
36. (e) Anderson, J. D.; McDonald, E. M.; Lee, P. A.; Anderson, M. L.; Ritchie, E. L.; Hall, H. K.; Hopkins, T.; Nash, E. A.; Wang, J.; Padias, A.; Thayumanavan, S.; Barlow, S.; Marder, S. R.; Jabbour, G.; Shaheen, S.; Kippelen, B.; Peyghambarian, N.; Wightman, R. M.; Armstrong, N. R. J. Am. Chem. Soc. 1998, 120, 9646-9655.
37. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H. J.; Hommes, N. J. R. V J. Am. Chem. Soc. 1996, 118, 6317-6318.
38. (a) Corminboeuf, C.; Hein, T.; Seifert, G.; Schleyer, P. v. R. J. Phys. Chem. Chem. Phys. 2004, 6, 273-276.
39. (b) Chen, Z. F.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842-3888.
40. (c) Fallah-Bagher-Shaidaei, H.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Org. Lett. 2006, 8, 863-866.
41. Schleyer, P. v. R.; Manoharan, M.; Wang, Z. X.; Kiran, B.; Jiao, H.; Puchta, R.; Hommes, N. J. R. V. Org. Lett. 2001, 3, 2465-2468.
42. (a) Kutzelnigg, W. Isr. J. Chem. 1980, 19, 193-200.
43. (b) Pipek, J.; Mezey, P. G. J. Chem. Phys. 1989, 90, 4916-4926.
44. (c) Malkin, V. G.; Malkina, O. L.; Casida, M. E.; Salahub, D. R. J. Am. Chem. Soc. 1994, 116, 5898-5908.
45. (a) Corminboeuf, C.; Heine, T.; Weber, J. Org. Lett. 2003, 5, 1127-1130.
46. (b) Moran, D.; Manoharan, M.; Heine, T.; Schleyer, P. v. R. Org. Lett. 2003, 5, 23-26.
47. (c) Heine, T.; Schleyer, P. v. R.; Corminboeuf, C.; Seifert, G.; Reviakine, R.; Weber, J. J. Phys. Chem. A 2003, 107, 6470-6475.
48. Schleyer, P. v. R.; Manoharan, M.; Jiao, H.; Stahl, F. Org. Lett. 2001, 3, 3643-3646.