Heptacene: Increased persistence of a 4n+2 π-electron polycyclic aromatic hydrocarbon by oxidation to the 4n π-electron dication

Angewandte Chemie - International Edition

Volumn 52, Issue 37, 2013, Pages 9818-9820

  Einholz, Ralf ^a   Bettinger, Holger F ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

aromaticity; dications; heptacene; sulfuric acid; UV Vis spectroscopy

Indexed keywords

AROMATICITIES; DICATIONS; HEPTACENE; ROOM TEMPERATURE; TETRACENE; UV/ VIS SPECTROSCOPY;

SULFURIC ACID; ULTRAVIOLET VISIBLE SPECTROSCOPY;

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 84883553955     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201209722     Document Type: Article

References (50)

1. E. Clar, Ber. Dtsch. Chem. Ges. B 1942, 75, 1330.
2. C. Marschalk, Bull. Soc. Chim. Fr. 1943, 10, 511
3. E. Clar, C. Marschalk, Bull. Soc. Chim. Fr. 1950, 17, 444
4. C. Marschalk, Bull. Soc. Chim. Fr. 1941, 8, 354.
5. W. J. Bailey, C.-W. Liao, J. Am. Chem. Soc. 1955, 77, 992.
6. B. Boggiano, E. Clar, J. Chem. Soc. 1957, 2681.
7. C. Tönshoff, H. F. Bettinger, Top. Curr. Chem. 2013, DOI:.
8. D. Biermann, W. Schmidt, J. Am. Chem. Soc. 1980, 102, 3163.
9. R. Mondal, B. K. Shah, D. C. Neckers, J. Am. Chem. Soc. 2006, 128, 9612.
10. R. Mondal, C. Toenshoff, D. Khon, D. C. Neckers, H. F. Bettinger, J. Am. Chem. Soc. 2009, 131, 14281
11. H. F. Bettinger, R. Mondal, D. C. Neckers, Chem. Commun. 2007, 5209.
12. R. Mondal, A. N. Okhrimenko, B. K. Shah, D. C. Neckers, J. Phys. Chem. B 2008, 112, 11.
13. R. Mondal, R. M. Adhikari, B. K. Shah, D. C. Neckers, Org. Lett. 2007, 9, 2505.
14. C. Tönshoff, H. F. Bettinger, Angew. Chem. 2010, 122, 4219
15. Angew. Chem. Int. Ed. 2010, 49, 4125.
16. S. S. Zade, N. Zamoshchik, A. R. Reddy, G. F. Marueli, D. Sheberla, M. Bendikov, J. Am. Chem. Soc. 2011, 133, 10803
17. S. S. Zade, M. Bendikov, J. Phys. Org. Chem. 2012, 25, 452.
18. J. Heiss, K.-P. Zeller, A. Rieker, Org. Mass Spectrom. 1969, 2, 1325
19. R. P. Bula, I. M. Oppel, H. F. Bettinger, J. Org. Chem. 2012, 77, 3538.
20. B. Purushothaman, S. R. Parkin, J. E. Anthony, Org. Lett. 2010, 12, 2060.
21. A. J. Athans, J. B. Briggs, W. Jia, G. P. Miller, J. Mater. Chem. 2007, 17, 2636.
22. J. R. Dias, K. K. Koehler, Polycyclic Aromat. Compd. 1995, 5, 79
23. E. Clar, Polycyclic Hydrocarbons, Vol. I, Academic Press, London und Springer, Berlin, 1964.
24. E. de Boer, S. I. Weissmann, J. Am. Chem. Soc. 1958, 80, 4549
25. V. Gold, F. L. Tye, J. Chem. Soc. 1952, 2172
26. K. W. Bowers, F. J. Weigert, J. Chem. Phys. 1966, 44, 416
27. J. R. Bolton, J. Chem. Phys. 1967, 46, 408
28. K. W. Bowers, J. E. Butler, F. J. Weigert, J. Chem. Phys. 1967, 46, 409
29. R. Makela, M. Vuolle, Fin. Chem. Lett. 1984, 3, 66
30. T. M. Halasinski, D. M. Hudgins, F. Salama, L. J. Allamandola, T. Bally, J. Am. Chem. Soc. 2000, 104, 748
31. for anions see also, P. Balk, G. J. Hoijtink, J. W. H. Schreurs, Receuil 1957, 76, 813.
32. H. Angliker, E. Rommel, J. Wirz, Chem. Phys. Lett. 1982, 87, 208
33. H. Angliker, F. Gerson, J. Lopez, J. Wirz, Chem. Phys. Lett. 1981, 81, 242
34. A. N. Sidorov, Zh. Fiz. Khim. 1974, 48, 1571
35. D. Distler, G. Hohlneicher, Chem. Phys. Lett. 1970, 7, 345.
36. J. Szczepanski, J. Drawdy, C. Wehlburd, M. Vala, Chem. Phys. Lett. 1995, 245, 539
37. S. Hirata, M. Head-Gordon, J. Szczepanski, M. Vala, J. Phys. Chem. A 2003, 107, 4940.
38. F. Cataldo, S. Iglesias-Groth, A. Manchado, Spectrochim. Acta Part A 2012, 77, 998. The optical spectra for anthracene, tetracene, and pentacene in oleum were incorrectly assigned to their radical cations. The optical spectra in Figure 3 and 4 in this reference are those of the anthracene, tetracene, and pentacene dications. Compare with Refs. [8a, 17g,h, 18c,d].
39. F. Neese, J. Chem. Phys. 2003, 119, 9428. For technical details, see Supporting Information.
40. D. A. Forsyth, G. A. Olah, J. Am. Chem. Soc. 1976, 98, 4086.
41. J. Ivanic, J. Chem. Phys. 2003, 119, 9364. For technical details, see Supporting Information.
42. B. Hajgatõ, D. Szieberth, P. Geerlings, F. De Proft, M. S. Deleuze, J. Chem. Phys. 2009, 131, 224321.
43. M. Baldo, G. Piccitto, R. Pucci, P. Tomasello, Phys. Lett. A 1983, 95, 201
44. M. Bendikov, H. M. Duong, K. Starkey, K. N. Houk, E. A. Carter, F. Wudl, J. Am. Chem. Soc. 2004, 126, 7416
45. J. Hachmann, J. J. Dorando, M. Avilés, G. K.-L. Chan, J. Chem. Phys. 2007, 127, 134309
46. Z. Qu, D. Zhang, C. Liu, Y. Jiang, J. Phys. Chem. A 2009, 113, 7909
47. D. Casanova, M. Head-Gorden, Phys. Chem. Chem. Phys. 2009, 11, 9779
48. H. F. Bettinger, Pure Appl. Chem. 2010, 82, 905.
49. E. Clar, The Aromatic Sextet, Wiley-Interscience, London, 1972.
50. J. Dominikowska, M. Palusiak, Phys. Chem. Chem. Phys. 2011, 13, 11976.