Molecular propellers that consist of dehydrobenzo[14]annulene blades

Chemistry - A European Journal

Volumn 18, Issue 40, 2012, Pages 12814-12824

  Nobusue, Shunpei ^a   Mukai, Yuichi ^a   Fukumoto, Yo ^a   Umeda, Rui ^a,b   Tahara, Kazukuni ^a   Sonoda, Motohiro ^a,c   Tobe, Yoshito ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KANSAI UNIVERSITY   (Japan)

^c Osaka Prefecture University   (Japan)

Author keywords

activation barrier; annulenes; density functional calculations; fused ring systems; propeller shaped compounds

Indexed keywords

ACTIVATION BARRIERS; ANNULENE RINGS; ANNULENES; BASIS SETS; BENZENE RING; DFT CALCULATION; FUNCTIONALS; FUSED-RING SYSTEM; INTERCONVERSIONS; NMR MEASUREMENTS; NMR STUDIES; PROPELLER-SHAPED COMPOUNDS; STERIC REPULSIONS; SYMMETRIC CONFORMATIONS; SYMMETRIC STRUCTURES; TRANSITION STATE; VARIABLE TEMPERATURE; X-RAY CRYSTALLOGRAPHIC ANALYSIS;

ACETYLENE; BENZENE; DENSITY FUNCTIONAL THEORY; ENERGY BARRIERS; LIGHTING; NAPHTHALENE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

PROPELLERS;

EID: 84867064986     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201201061     Document Type: Article

References (55)

1. For a review on overcrowded polycyclic aromatic compounds, see:, R. A. Pascal, Jr., Chem. Rev. 2006, 106, 4809-4819.
2. M. B. Hursthouse, V. B. Smith, J. Fluorine Chem. 1977, 10, 145-155
3. C. S. Frampton, D. D. MacNicol, S. J. Rowan, J. Mol. Struct. 1997, 405, 169-178
4. Y. Wang, A. D. Stretton, M. C. McConnell, P. A. Wood, S. Parsons, J. B. Henry, A. R. Mount, T. H. Galow, J. Am. Chem. Soc. 2007, 129, 13193-13200.
5. L. Barnett, D. M. Ho, K. K. Baldridge, R. A. Pascal, Jr., J. Am. Chem. Soc. 1999, 121, 727-733.
6. D. Peña, D. Pérez, E. Guitián, L. Castedo, Org. Lett. 1999, 1, 1555-1557
7. D. Peña, A. Cobas, D. Pérez, E. Guitián, L. Castedo, Org. Lett. 2000, 2, 1629-1632.
8. M. A. Bennett, M. R. Kopp, E. Wenger, A. C. Willis, J. Organomet. Chem. 2003, 667, 8-15.
9. C. Romero, D. Peña, D. Pérez, E. Guitián, Chem. Eur. J. 2006, 12, 5677-5684.
10. J. M. Alonso, A. E. Díaz-Álvarez, A. Criado, D. Pérez, D. Peña, E. Guitián, Angew. Chem. 2012, 124, 177-181
11. Angew. Chem. Int. Ed. 2012, 51, 173-177.
12. K. Zimmermann, R. Goddard, C. Krüger, M. W. Haenal, Tetrahedron Lett. 1996, 37, 8371-8374
13. J. K. Gimzewski, C. Joachim, P. R. Schlittler, V. Langlais, H. Tang, I. Johannsen, Science 1998, 281, 531-533
14. B. Iglesias, D. Peña, D. Pérez, E. Guitián, L. Castedo, Synlett 2002, 0486-0488.
15. A. Pradhan, P. Dechambenoit, H. Bock, F. Durola, Angew. Chem. 2011, 123, 12790-12793
16. Angew. Chem. Int. Ed. 2011, 50, 12582-12585.
17. T. Yoshimura, A. Inaba, M. Sonoda, K. Tahara, Y. Tobe, R. V. Williams, Org. Lett. 2006, 8, 2933-2936.
18. K. Tahara, T. Yoshimura, M. Sonoda, Y. Tobe, R. V. Williams, J. Org. Chem. 2007, 72, 1437-1442.
19. K. P. Baldwin, A. J. Matzger, D. A. Scheiman, C. A. Tessier, K. P. C. Vollhardt, W. J. Youngs, Synlett 1995, 1216-1218
20. J. A. Marsden, J. J. Miller, M. M. Haley, Angew. Chem. 2004, 116, 1726-1729
21. Angew. Chem. Int. Ed. 2004, 43, 1694-1697.
22. S. Toyota, T. Yamamori, T. Makino, Tetrahedron 2001, 57, 3521-3528
23. T. Makino, S. Toyota, Bull. Chem. Soc. Jpn. 2005, 78, 917-928
24. S. Toyota, Chem. Rev. 2010, 110, 5398-5424.
25. Recently, Haley and co-workers reported the synthesis- and optical properties of trefoil-shaped molecules in which three [14]DBA rings were fused to a central triphenylene, -dehydrobenzo[12]annulene, or -dehydrobenzo[18] annulene core. However, because of the large core size, these compounds would not exhibit hindered rotation around the [14]DBA blades. See:, T. Takeda, A. G. Fix, M. M. Haley, Org. Lett. 2010, 12, 3824-3827.
26. C. Huynh, G. Linstrumelle, Tetrahedron 1988, 44, 6337-6344
27. J. A. John, J. M. Tour, J. Am. Chem. Soc. 1994, 116, 5011-5012.
28. R. Diercks, J. C. Armstrong, R. Boese, K. P. C. Vollhardt, Angew. Chem. 1986, 98, 270-271
29. Angew. Chem. Int. Ed. Engl. 1986, 25, 268-269
30. T. X. Neenan, G. M. Whitesides, J. Org. Chem. 1988, 53, 2489-2496
31. M. Sonoda, A. Inaba, K. Itahashi, Y. Tobe, Org. Lett. 2001, 3, 2419-2421.
32. S. Ito, H. Inabe, N. Morita, K. Ohta, T. Kitamura, K. Imafuku, J. Am. Chem. Soc. 2003, 125, 1669-1680
33. J. Nierle, D. Barth, D. Kuck, Eur. J. Org. Chem. 2004, 867-872
34. M. Hasegawa, H. Enozawa, Y. Kawabata, M. Iyoda, J. Am. Chem. Soc. 2007, 129, 3072-3073
35. M. Schmittel, P. Mal, Chem. Commun. 2008, 960-962.
36. Y. Zhao, N. E. Schultz, D. G. Truhlar, J. Chem. Phys. 2005, 123, 161103
37. Y. Zhao, N. E. Schultz, D. G. Truhlar, J. Chem. Theory Comput. 2006, 2, 364-382
38. Y. Zhao, D. G. Truhar, J. Chem. Theory Comput. 2006, 2, 1009-1018
39. S. Toyota, H. Miyahara, M. Goichi, S. Yamasaki, T. Iwanaga, Bull. Chem. Soc. Jpn. 2009, 82, 931-945.
40. K. P. Baldwin, A. J. Matzger, D. A. Scheiman, C. A. Tessier, K. P. C. Vollhardt, W. J. Youngs, Synlett 1995, 1215-1218
41. H. Hinrichs, A. K. Fischer, P. G. Jones, H. Hopf, M. M. Haley, Org. Lett. 2005, 7, 3793-3795
42. H. S. Blanchette, S. C. Brand, H. Naruse, T. J. R. Weakley, M. M. Haley, Tetrahedron 2000, 56, 9581-9588
43. M. J. O'Connor, R. B. Yelle, L. N. Zakharov, M. M. Haley, J. Org. Chem. 2008, 73, 4424-4432.
44. W. B. Wan, M. M. Haley, J. Org. Chem. 2001, 66, 3893-3901
45. K. West, C. Wang, A. S. Batsanov, M. R. Bryce, J. Org. Chem. 2006, 71, 8541-8544.
46. Q. Zhou, P. J. Carroll, T. M. Swager, J. Org. Chem. 1994, 59, 1294-1301
47. I. Hisaki, T. Eda, M. Sonoda, H. Niino, T. Sato, T. Wakabayashi, Y. Tobe, J. Org. Chem. 2005, 70, 1853-1864.
48. For the chemical-shift calculations we used the HF method because this had been shown to be the most reliable means for evaluating the chemical shifts (i.e., magnetic properties) of annulenes. For example, see:, R. V. Williams, J. R. Armantrout, B. Twamley, R. H. Mitchell, T. R. Ward, S. Bandyopadhyay, J. Am. Chem. Soc. 2002, 124, 13495-13505.
49. R. Jain, T. Bally, P. R. Rablen, J. Org. Chem. 2009, 74, 4017-4023
50. T. Bally, P. R. Rablen, J. Org. Chem. 2011, 76, 4818-4830
51. M. Cossi, G. Scalmani, N. Rega, V. Barone, J. Chem. Phys. 2002, 117, 43-54.
52. Y. Okamoto, T. Ikai, Chem. Soc. Rev. 2008, 37, 2593-2608
53. T. Ikai, Y. Okamoto, Chem. Rev. 2009, 109, 6077-6101.
54. A. R. Lippert, A. Naganawa, V. L. Keleshian, J. W. Bode, J. Am. Chem. Soc. 2010, 132, 15790-15799
55. M. He, J. W. Bode, Proc. Natl. Acad. Sci. USA 2011, 108, 14752-14756.