Browse > Article
http://dx.doi.org/10.5012/bkcs.2004.25.11.1641

Synthesis and Shuttling Behavior of Rotaxanes Consisting of Crown Ether Wheel and Disulfide Dumbbell with Two Ammonium Centers  

Furusho, Yoshio (Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University)
Sanno, Ryoko (Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University)
Oku, Tomoya (Department of Organic and Polymeric Materials, Tokyo Institute of Technology)
Takata, Toshikazu (Department of Organic and Polymeric Materials, Tokyo Institute of Technology)
Publication Information
Bulletin of the Korean Chemical Society / v.25, no.11, 2004 , pp. 1641-1644 More about this Journal
Abstract
Several [2]- and [3]rotaxanes bearing some functional groups on their wheel components and spacers with different lengths between two ammonium centers on their dumbbell components were prepared in good yields from dibenzo-24-crown-8-ether derivatives and dumbbell-shaped bis(sec-ammonium salt)s having a centrally located disulfide linkage, by utilizing the reversible thiol-disulfide interchange reaction. The shuttling behaviors of the [2]rotaxanes were investigated by $^1H$ NMR by use of the spin polarization transfer-selective inversion recovery technique. It was found that the change in spacer length in the axle resulted in a drastic change in shuttling rate of the [2]rotaxanes, although the introduction of the functional groups to the wheels did not affect the shuttling behavior at all.
Keywords
[2]Rotaxane; Crown ether; Ammonium salt; Disulfide; Shuttling;
Citations & Related Records

Times Cited By Web Of Science : 3  (Related Records In Web of Science)
Times Cited By SCOPUS : 3
연도 인용수 순위
1 Kelly, T. R.; Tellitu, I.; Sestelo, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1866.   DOI   ScienceOn
2 Sutherland, I. O. Annu. Rep. NMR Spectrosc. 1971, 4, 71.
3 Pease, A. R.; Jeppesen, J. O.; Stoddart, J. F.; Luo, Y.; Collier, C. P.; Heath, J. Acc. Chem. Res. 2001, 34, 433.   DOI   ScienceOn
4 Molecular Catenanes, Rotaxanes and Knots; Sauvage, J.-P.; Dietrich-Buchecker, C., Eds.; Wiley-VCH: Weinheim, 1999.
5 Diedrich, F.; Echegoyen, L.; Gomez-Lopez, M.; Kessinger, R.; Stoddart, J. F. J. Chem. Soc., Perkin Trans. 2: Phys. Org. Chem. 1999, 1577-1586.
6 Furusho, Y.; Hasegawa, H.; Tsuboi, A.; Kihara, N.; Takata, T. Chem. Lett. 2000, 18.
7 Oku, T.; Furusho, Y.; Takata, T. submitted to Macromolecules.
8 Sandstrom, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
9 Dahlquist, F. W.; Longmur, K. J.; Du Vernet, R. B. J. Magn. Reson. 1975, 17, 406.
10 Furusho, Y.; Oku, T.; Hasegawa, H.; Tsuboi, A.; Kihara, N.; Takata, T. Chem. Eur. J. 2003, 9, 2895.   DOI   ScienceOn
11 Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458.   DOI   ScienceOn
12 Ashton, P. R.; Baxter, I.; Cantrill, S. J.; Fyfe, M. C. T.; Glink, P. T.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem. Int. Ed. 1998, 37, 1294.   DOI   ScienceOn
13 Schill, G. Catenanes, Rotaxanes and Knots; Academic: New York, 1971.
14 Ben-David Blanca, M.; Maimon, E.; Kost, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2216.   DOI   ScienceOn
15 Oku, T.; Furusho, Y.; Takata, T. Angew. Chem., Int. Ed. Engl. 2004, 43, 966.   DOI   ScienceOn
16 Collier, C. P.; Mattersteig, G.; Wong, E. W.; Luo, Y.; Beverly, K.; Sampaio, J.; Raymo, F. M.; Stoddart, J. F.; Heath, J. R. Science 2000, 289, 1172.   DOI   ScienceOn
17 Oku, T.; Furusho, Y.; Takata, T. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 119.   DOI   ScienceOn