Axially chiral facial amphiphiles with a dihydronaphthopentaphene structure as molecular tweezers for swnts

Chemistry - A European Journal

Volumn 15, Issue 42, 2009, Pages 11187-11196

  Marquis, Renaud ^a   Kulikiewicz, Krystyna ^a   Lebedkin, Sergei ^b   Kappes, Manfred M ^b   Meunier, Charles Mioskowski Stéphane ^a   Wagner, Alain ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Amphiphiles; Anthracenes; Carbon nanotubes; Chirality pi interactions

Indexed keywords

CIRCULAR DICHROISM SPECTRA; CO CONVERSION; DIELS-ALDER REACTION; ENANTIOMERIC RESOLUTION; FACIAL AMPHIPHILES; MOLECULAR TWEEZERS; OPTICAL ACTIVITY; SOLUBILISATION;

ADSORPTION; ANTHRACENE; CARBON MONOXIDE; CARBON NANOTUBES; CHEMICAL REACTIONS; CHIRALITY; CIRCULAR DICHROISM SPECTROSCOPY; DICHROISM; ENANTIOMERS; OPTICAL MATERIALS; SINGLE CRYSTALS; SINGLE-WALLED CARBON NANOTUBES (SWCN); STEREOCHEMISTRY;

AMPHIPHILES;

6,15 DIHYDRONAPHTHO(2,3 C)PENTAPHENE; 6,15-DIHYDRONAPHTHO(2,3-C)PENTAPHENE; ANTHRACENE; ANTHRACENE DERIVATIVE; CARBON NANOTUBE;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; STEREOISOMERISM;

ANTHRACENES; CIRCULAR DICHROISM; NANOTUBES, CARBON; STEREOISOMERISM;

EID: 70350499756     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200901545     Document Type: Article

References (40)

1. Y. Cheng, D. M. Ho, G. R. Gottlieb, D. Kahne, J. Am. Chem. Soc. 1992, 114, 7319-7320.
2. a) E. T. Kaiser, F. J. Kezdy, Science 1984, 223, 249-255;
3. b) S. Taka- hashi, Biochemistry 1990, 29, 6257-6264.
4. a) F. M. Menger, J. L. Sorrells, J. Am. Chem. Soc. 2006, 128, 4960- 4961;
5. b) U. Taotafa, D. B. McMullin, S. C. Lee, L. D. Hansen, P. B. Sauvage, Org. Lett. 2000, 2, 4117-4120;
6. c) J. Lu, S.-Z. Kang, S. L. Xu, Q.-D. Zeng, C. Wang, L.-J. Wan, C.-L. Bai, Chem. Commun. 2003, 1498-1499;
7. d) Z. Zhong, J. Yan, Y. Zhao, Langmuir 2005, 21, 6235-6239;
8. e) S.-L. Xu, S.-Z. Kang, J. Lu, Y-H. Liu, C. Wang, L.-J. Wan, C.-L. Bai, Surfactant Sci. Ser. 2003, 527, L171-L176.
9. R. Marquis, C. Greco, I. Sadokierska, S. Lebedkin, M. M. Kappes, T. Michel, L. Alvarez, J.-L. Sauvajol, S. Meunier, C. Mioskowski, Nano Lett. 2008, 8, 1830-1835.
10. Z. Chen, J. Appenzeller, J. Knoch, Y-M. Lin, P. Avouris, Nano Lett. 2005, 5, 1497-1502.
11. a) D. Yuan, J. Liu, Small 2007, 3, 366-367;
12. b) R. Krupke, F. Hennrich, H. V. Loehneysen, M. M. Kappes, Science 2003, 301, 344-347;
13. c) M. S. Arnold, A. A. Green, J. F. Hulvát, S. I. Stupp, M. C. Hersam, Nat. Nanotechnol. 2006, 7, 60-65;
14. d) M. S. Strano, M. Zheng, A. Jagota, G. B. Onoa, D. A. Heller, P. W. Barone, M. L. Usrey, Nano Lett. 2004, 4, 543-550;
15. e) A. Nish, J.-Y. Hwang, J. Doig, R. J. Nicholas, Nat. Nanotechnol. 2007, 2, 640.
16. a) N. Nish, J.-Y. Hwang, J. Doig, R. J. Nicholas, Nat. Nanotechnol. 2007, 2, 640-646;
17. b) F. Chen, B. Wang, Y. Chen, L.-J. Li, Nano Lett. 2007, 7, 3013-3017;
18. c) R. M. Tromp, A. Afzali, M. Freitag, D. B. Mitzi, Z. Chen, Nano Lett. 2008, 8, 469-472.
19. a) N. Komatsu, J. Inclusion Phenom. Macrocyclic Chem. 2008, 67, 195-216;
20. b) X. Peng, N. Komatsu, S. Bhattacharya, T. Shimawaki, J. Aonuma, T. Kimura, A. Osuka, Nat. Nanotechnol. 2007, 2, 361-365;
21. c) X. Peng, N. Komatsu, T. Kimura, A. Osuka, J. Am. Chem. Soc. 2007, 129, 15947-15953;
22. d) X. Peng, F. Wang, T. Kimura, N. Komatsu, A. Osuka, J. Phys. Chem. C2009, 113, 9108-9113.
23. D. Biermann, W. Schmidt, J. Am. Chem. Soc. 1980, 102, 3173-3181.
24. a) N. Harada, Y. Takuma, H. Uda, J. Am. Chem. Soc. 1976, 98, 5408-5409;
25. b) N. Harada, Y. Takuma, H. Uda, Bull. Chem. Soc. Jpn. 1977, 50, 2033-2038.
26. E. Ciar, Chem. Ber. 1948, 81, 169-175.
27. a) A. Sygula, R. Sygula, A. Ellern, P. W. Rabideau, Org. Lett. 2003, 5, 2595-2597;
28. b) R. Schweninger, Y. Ramondenc, K. Wurst, J. Schlögl, B. Kräutler, Chem. Eur. J. 2000, 6, 1214-1223;
29. c) J. C. Adrian, Jr., T. M. Ovitt, Tetrahedron: Asymmetry 1996, 7, 2407-2410;
30. d) M. A. Petti, T. J. Shepodd, R. E. Barrans, D. A. Dougherty, J. Am. Chem. Soc. 1988, 110, 6825-6840.
31. B. C Ranu, P. Dutta, A. Sarkar, J. Org. Chem. 1998, 63, 6027-6028.
32. a) M. N. Tahir, P. Theato, W. E. G. Mueller, H. C. Schroeder, A. Janshoff, J. Zhang, J. Huth, W. Tremei, Chem. Commun. 2004, 2848- 2849;
33. b) Z. Huang, J. I. Park, D. S. Watson, P. Hwang, F. C. Szoka, Jr., Bioconjugate Chem. 2006, 17, 1592-1600.
34. a) H. Wissmann, H. J. Kleiner, Angew. Chem. 1980, 92, 129-130;
35. Angew. Chem. Int. Ed. 1980, 19, 133-134;
36. b) J. Klose, C. Mollenkopf, D. Wehle, C.-W. Zhang, L. A. Carpino, P. Henklein, Chem. Commun. 1999, 1847-1848;
37. c) M. Schwarz, Synlett 2000, 1369.
38. S. M. Bachilo, M. S. Strano, C. Kittrell, R. H. Hauge, R. E. Smalley, R. B. Weisman, Science 2002, 298, 2361-2366.
39. S. Lebedkin, K. Arnold, F. Hennrich, R. Krupke, B. Renker, M. M. Kappes, New J. Phys. 2003, 5, 140.
40. To date, and as underlined by N. Komatsu (ref. [8]), CD measurements do not allow the discrimination of optical activity due to SWNTs and induced optical activity of racemic SWNTs (as observed, for example, by adsorbing DNA on a racemic mixture of SWNTs; G. Dukovic, M. Balaz, P. Doak, N. D. Bérova, M. Zheng, R. S. Mclean, L. E. Brus, J. Am. Chem. Soc. 2006, 128, 9004-9005). For this reason, and because of the very high optical activity of compounds 1, extensive washings were required for its complete removal from the SWNT samples in order to unequivocally measure the optical enrichment due to the chiral SWNTs. In this process, we incurred a dramatic loss in material, which prevented us from recording CD signals strong enough to be conclusive.