Structures and conformational analysis of 1,8-bis(9-triptycylethynyl) anthracene and its derivatives as prototypes of molecular spur gears

Chemistry Letters

Volumn 40, Issue 3, 2011, Pages 312-314

  Toyota, Shinji ^a   Shimizu, Takamasa ^a   Iwanaga, Tetsuo ^a   Wakamatsu, Kan ^a  

^a OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79951929177     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2011.312     Document Type: Article

References (35)

1. V. Balzani, M. Venturi, A. Credi, Molecular Devices and Machines: A Journey into the Nanoworld, Wiley-VCH, Weinheim, 2003, Chap. 11.
2. G. S. Kottas, L. I. Clarke, D. Horinek, J. Michl, Chem. Rev. 2005, 105, 1281.
3. Selected examples of molecular gears with various aromatic wheels. a) S. Ogi, T. Ikeda, R. Wakabayashi, S. Shinkai, M. Takeuchi, Chem. - Eur. J. 2010, 16, 8285.
4. K. Fuji, T. Oka, T. Kawabata, T. Kinoshita, Tetrahedron Lett. 1998, 39, 1373.
5. A. M. Stevens, C. J. Richards, Tetrahedron Lett. 1997, 38, 7805.
6. G. Vives, H.-P. J. de Rouville, A. Carella, J.-P. Launay, G. Rapenne, Chem. Soc. Rev. 2009, 38, 1551.
7. L. Zhao, Z. Li, T. Wirth, Chem. Lett. 2010, 39, 658.
8. J. H. Chong, M. J. MacLachlan, Chem. Soc. Rev. 2009, 38, 3301.
9. T. M. Swager, Acc. Chem. Res. 2008, 41, 1181.
10. H. Iwamura, K. Mislow, Acc. Chem. Res. 1988, 21, 175, and references therein.
11. Y. Kawada, H. Sakai, M. Oguri, G. Koga, Tetrahedron Lett. 1994, 35, 139.
12. W. Setaka, T. Nirengi, C. Kabuto, M. Kira, J. Am. Chem. Soc. 2008, 130, 15762.
13. G. Yamamoto, S. Ohta, M. Kaneko, K. Mouri, M. Ohkuma, R. Mikami, Y. Uchiyama, M. Minoura, Bull. Chem. Soc. Jpn. 2005, 78, 487.
14. G. Yamamoto, Tetrahedron 1990, 46, 2761.
15. T. R. Kelly, M. C. Bowyer, K. V. Bhaskar, D. Bebbington, A. Garcia, F. Lang, M. H. Kim, M. P. Jette, J. Am. Chem. Soc. 1994, 116, 3657.
16. C. Joachim, H. Tang, F. Moresco, G. Rapenne, G. Meyer, Nanotechnology 2002, 13, 330.
17. L. Grill, K.-H. Rieder, F. Moresco, G. Rapenne, S. Stojkovic, X. Bouju, C. Joachim, Nat. Nanotechnol. 2007, 2, 95.
18. G. Rapenne, G. Jimenez-Bueno, Tetrahedron 2007, 63, 7018.
19. M. A. Garcia-Garibay, C. E. Godinez, Cryst. Growth Des. 2009, 9, 3124.
20. S. Toyota, T. Yamamori, T. Makino, Tetrahedron 2001, 57, 3521.
21. S. Toyota, T. Yamamori, M. Asakura, M. Oki, Bull. Chem. Soc. Jpn. 2000, 73, 205.
22. P. K. T. Mew, F. Vögtle, Angew. Chem., Int. Ed. Engl. 1979, 18, 159.
23. S. Toyota, Chem. Rev. 2010, 110, 5398.
24. J. C. Bryan, R. A. Sachleben, A. A. Gakh, G. J. Bunick, J. Chem. Crystallogr. 1999, 29, 513.
25. D. K. Frantz, K. K. Baldridge, J. S. Siegel, Chimia 2009, 63, 201.
26. S. Toyota, M. Goichi, M. Kotani, Angew. Chem., Int. Ed. 2004, 43, 2248.
27. S. Toyota, M. Goichi, M. Kotani, M. Takezaki, Bull. Chem. Soc. Jpn. 2005, 78, 2214.
28. T. Ishikawa, T. Shimasaki, H. Akashi, T. Iwanaga, S. Toyota, M. Yamasaki, Bull. Chem. Soc. Jpn. 2010, 83, 220.
29. S. Toyota, T. Kawakami, R. Shinnishi, R. Sugiki, S. Suzuki, T. Iwanaga, Org. Biomol. Chem. 2010, 8, 4997.
30. S. Toyota, Chem. Lett. 2011, 40, 12.
31. M. Goichi, K. Segawa, S. Suzuki, S. Toyota, Synthesis 2005, 2116.
32. B. Bossenbroke, D. C. Sanders, H. M. Curry, H. Shechter, J. Am. Chem. Soc. 1969, 91, 371.
33. Supporting Information (spectroscopic data of the final products, calculated structures, and VT NMR spectra) is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.
34. Crystallographic data reported in this manuscript have been deposited with Cambridge Crystallographic Data Centre as supplementary publication Nos. CCDC-802618 (2a) and -802619 (4a). Copies of the data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge, CB2 1EZ, U.K.; fax: +44 1223 336033); or deposit@ccdc.cam.ac.uk).
35. Calculations were carried out with M05 density functional and 6-31G basis set. This level of calculations reasonably reproduced the X-ray structures of 2a and 4a. Y. Zhao, D. G. Truhlar, Acc. Chem. Res. 2008, 41, 157.