Molecular self-assembly inhibition leads to basket-shaped cyclophane formation with chiral dynamics

Journal of Physical Chemistry A

Volumn 112, Issue 14, 2008, Pages 3094-3103

  Wang, Wei ^a,d   Bain, Alex D ^a,b   Wang, Li Qiong ^a,c   Exarhos, Gregory J ^a,c   Li, Alexander D Q ^a  

^a WASHINGTON STATE UNIVERSITY   (United States)

^b MCMASTER UNIVERSITY   (Canada)

^c PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ENTHALPIES; CHIRAL STRUCTURES; CONFORMATIONAL DYNAMICS; CYCLIC COMPOUNDS; CYCLOPHANE; LEFT-HANDEDNESS (LH); LOW TEMPERATURE (LTR); MACRO-CYCLIC; MOLECULAR SELF ASSEMBLIES; MULTIMERIC; N MR STUDIES; PERYLENE (PE); PERYLENE DERIVATIVES; ROOM-TEMPERATURE (RT); UNIMOLECULAR;

CONFORMATIONS; CYCLIZATION; DIMERS; DYNAMICS; ELECTRON TRANSITIONS; MOLECULES; MONOMERS; NUCLEAR MAGNETIC RESONANCE; OLIGOMERS; OPTICAL DEVICES;

SELF ASSEMBLY;

ETHER DERIVATIVE; PERYLENE;

ARTICLE; CHEMISTRY; CYCLIZATION; DIMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ROTATION; STEREOISOMERISM;

CYCLIZATION; DIMERIZATION; ETHERS, CYCLIC; MAGNETIC RESONANCE SPECTROSCOPY; PERYLENE; ROTATION; STEREOISOMERISM;

EID: 43049095771     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp077650a     Document Type: Article

References (33)

1. Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725-2828.
2. (a) Gabriel, G. J.; Sorey, S.; Iverson, B. L. J. Am. Chem. Soc. 2005, 127, 2637-2640.
3. (b) Neuteboom, E. E.; Van Hal, P. A.; Janssen, R. A. Chem.-Eur. J. 2004, 10, 3907-3918 and references therein.
4. (c) Kieran, A. L.; Pascu, S. I.; Jarrosson, T.; Gunter, M. J.; Sanders, J. K. M. Chem. Commun. 2005, 1842-1844.
5. (d) Li, Z. T.; Stein, P. C.; Becher, J.; Jensen, D.; Mork, P. Chem.-Eur. J. 1996, 2, 624-633.
6. (a) Stoddart, J. F.; Tseng, H.-R. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 4797-4800.
7. (b) Raehm, L.; Kern, J.-M.; Sauvage, J.-P.; Hamann, C.; Palacin, S.; Bourgoin, J.-P. Chem.-Eur. J. 2002, 8, 2153-2162.
8. (c) Kaiser, G.; Jarrosson, T.; Otto, S.; Ng, Y.-F.; Bond, A. D.; Sanders, J. K. M. Angew. Chem., Int. Ed. Engl. 2004, 43, 1959-1962.
9. (d) Aricó, F.; Badjic, J. D.; Cantrill, S. J.; Flood, A. H.; Leung, K. C.-F.; Liu, Y.; Stoddart, J. F. Top. Curr. Chem. 2005, 203-259.
10. (e) Fuller, A. M. L.; Leigh, D. A.; Lusby, P. J.; Slawin, A. M. Z.; Walker, D. B. J. Am. Chem. Soc. 2005, 127, 12612-12619.
11. (f) Leigh, D. A.; Lusby, P. J.; Slawin, A. M. Z.; Walker, D. B. Angew. Chem., Int. Ed. 2005, 44, 4557-4564.
12. Wang, W.; Wang, L. Q.; Palmer, B. J.; Exarhos, G. J.; Li, A. D. Q. J. Am. Chem. Soc. 2006, 128, 11150-11159.
13. Deng, N. L.; Marwaha, V. R.; Garcia, M. E.; Benesi, A.; Mallouk, T. E. Tetrahedron Lett. 1995, 36, 7599-7602.
14. Garcia, M. E.; Gavin, J. A.; Deng, N. L.; Andrievsky, A.; Mallouk, T. E. Tetrahedron Lett. 1996, 37, 8313-8316.
15. Nishimura, J.; Nakamura, Y.; Hayashida, Y.; Kudo, T. Acc. Chem. Res. 2000, 33 (10), 679-686 and references therein.
16. Das, B.; Abe, S. J. Phys. Chem. B 2006, 110 (47), 23806-23811.
17. Vignon, S. A.; Wong, J.; Tseng, H. R.; Stoddart, J. F. Org. Lett. 2004, 6, 1095-1098.
18. Wurthner, F.; Osswald, P.; Schmidt, R.; Kaiser, T.; Mansikkamaki, H.; Konemann, M.; Org. Lett. 2006, 8 (17), 3765-68.
19. Jones, B. A.; Ahrens, M. J.; Yoon, M. H.; Facchetti, A.; Marks, T. J.; Wasielewski, M. R. Angew. Chem., Int. Ed. 2004, 43 (46), 6363-6366.
20. Wurthner, F.; Stepaneko, V.; Chen, Z.; Saha-Moller, C.; Kocher, N.; Stalke, D. J. Org. Chem. 2004, 69, 7933-9.
21. Wurthner, F.; Sautter, A.; Schilling, J. J. Org. Chem. 2002, 67, 3037-44.
22. Wurthner, F.; Osswald, P.; Schmidt, R.; Kaiser, T.; Mansikkamaki, H.; Konemann, M. Org. Lett. 2006, 8 (17), 3765-68.
23. Chen, Z. J.; Debije, M. G.; Debaerdemaker, T.; Osswald, P.; Würthner, F. Chem. Phys. Chem. 2004, 5, 137-140.
24. Wang, W.; Wan, W.; Zhou, H.-H.; Niu, S.-Q.; Li, A. D. Q. J. Am. Chem. Soc. 2003, 125, 5248-5249.
25. Wang, W.; Han, J.; Wang, L.; Li, L.; Shaw, W.; Li, A. Nano Lett. 2003, 3, 455-458.
26. Wurthner, F.; Sautter, A.; Thalacker, C. Angew. Chem., Int. Ed. Engl. 2000, 39, 1243-1245.
27. Kanomata, N.; Ochiaia, Y. Tetrahedron Lett. 2001, 42, 1045-1048.
28. Bodwell, G. J.; Li, J.; Miller, D. O. Tetrahedron 1999, 55, 12939-12956.
29. Gutowsky, H. S.; Holm, C. H. J. Chem. Phys. 1956, 25, 1228-1234.
30. Jackman, L. M.; Cotton, F. A. Dynamic Nuclear Magnetic Resonance Spectroscopy; Academic Press: New York, 1975.
31. Sandstrom, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
32. Binsch, G. A. J. Am. Chem. Soc. 1969, 91, 1304-1309.
33. Bain, A. D.; Duns, G. J. Can. J. Chem. 1996, 74, 819-824.