Fluoreno[4,3-c]fluorene: A closed-shell, fully conjugated hydrocarbon

Organic Letters

Volumn 14, Issue 9, 2012, Pages 2426-2429

  Rose, Bradley D ^a   Vonnegut, Chris L ^a   Zakharov, Lev N ^a   Haley, Michael M ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84860617047     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300942z     Document Type: Article

References (29)

1. Balaban, A. T.; Banciu, M.; Ciorba, V. Annulenes, Benzo-, Hetero-, Homo-Derivatives and their Valence Isomers; CRC Press: Boca Raton, FL, 1987.
2. Hopf, H. Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives; Wiley-VCH: Weinheim, Germany, 2000.
3. Müeller, T. J. J.; Bunz, U. H. F. Functional Organic Materials: Syntheses, Strategies and Applications; Wiley-VCH: Weinheim, Germany, 2007.
4. Müllen, K.; Scherf, U. Organic Light Emitting Devices: Synthesis, Properties and Applications; Wiley-VCH: Weinheim, Germany, 2006.
5. Haley, M. M.; Tykwinski, R. R. Carbon-Rich Compounds: From Molecules to Materials; Wiley-VCH: Weinheim, Germany, 2006.
6. Anthony, J. E. Chem. Rev. 2006, 106, 5028-5048
7. Shimizu, A.; Tobe, Y. Angew. Chem., Int. Ed. 2011, 50, 6906-6910
8. Chase, D. T.; Rose, B. D.; McClintock, S. P.; Zakharov, L. N.; Haley, M. M. Angew. Chem., Int. Ed. 2011, 50, 1127-1130
9. Chase, D. T.; Fix, A. G.; Rose, B. D.; Weber, C. D.; Nobusue, S.; Stockwell, C. E.; Zakharov, L. N.; Lonergan, M. C.; Haley, M. M. Angew. Chem., Int. Ed. 2011, 50, 11103-11106
10. Chase, D. T.; Fix, A. G.; Kang, S. J.; Rose, B. D.; Weber, C. D.; Zhong, Y.; Zakharov, L. N.; Lonergan, M. C.; Nuckolls, C.; Haley, M. M., submitted.
11. Anthony, J. E.; Facchetti, A.; Heeney, M.; Marder, S. R.; Zhan, X. Adv. Mater. 2010, 22, 3876-3892
12. Cramer, C. J. Essentials of Computational Chemistry: Theories and Models; John Wiley & Sons Ltd: Chichester, U.K., 2002; pp 335-338.
13. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
14. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B: Condens. Matter 1988, 37, 785-789
15. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
16. All calculations were performed using: Frisch, M. J. Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009. See Supporting Information for the full citation.
17. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermochemical Data of Organic Compounds, 2nd ed.; Chapman and Hall: New York, 1986.
18. Fallah-Bagher-Shaidaei, H.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v R. Org. Lett. 2006, 8, 863-866
19. Kubo, T.; Shimizu, A.; Uruichi, M.; Yakushi, K.; Nakano, M.; Shiomi, D.; Sato, K.; Takui, T.; Morita, Y.; Nakasuji, K. Org. Lett. 2007, 9, 81-84
20. Sun, Z.; Huang, K.-W.; Wu, J. J. Am. Chem. Soc. 2011, 133, 11896-11899
21. Purushothaman, B.; Bruzek, M.; Parkin, S. R.; Miller, A.-F.; Anthony, J. E. Angew. Chem., Int. Ed. 2011, 50, 7013-7017
22. Gao, X.; Hodgson, J. L.; Jiang, D.; Zhang, S. B.; Nagase, S.; Miller, G. P.; Chen, Z. Org. Lett. 2011, 13, 3316-3319
23. Takano, Y.; Taniguchi, T.; Isobe, H.; Kubo, T.; Morita, Y.; Yamamoto, K.; Nakasuji, K.; Takui, T.; Yamaguchi, K. J. Am. Chem. Soc. 2002, 124, 11122-11130
24. Wittig, G.; Wiemer, W. Liebigs Ann. Chem. 1930, 483, 144-156
25. Brauer, H. D.; Reinsch, E. A. Ber. Bunsenges. Phys. Chem. 1973, 77, 348-353
26. Preis, E.; Scherf, U. Macromol. Rapid Commun. 2006, 27, 1105-1109
27. + to SCE, as described in: Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877-910
28. Reiss, H.; Heller, A. J. Phys. Chem. 1985, 89, 4207-4213
29. Sanz, F.; Daly, J. J. J. Chem. Soc., Perkin Trans. 2 1975, 1141-1145