Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

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)
  • Published : 2004.11.20
Download PDF
⟨ Previous Next ⟩

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

References

  1. Schill, G. Catenanes, Rotaxanes and Knots; Academic: New York, 1971.
  2. Molecular Catenanes, Rotaxanes and Knots; Sauvage, J.-P.; Dietrich-Buchecker, C., Eds.; Wiley-VCH: Weinheim, 1999.
  3. Pease, A. R.; Jeppesen, J. O.; Stoddart, J. F.; Luo, Y.; Collier, C. P.; Heath, J. Acc. Chem. Res. 2001, 34, 433. https://doi.org/10.1021/ar000178q
  4. 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. https://doi.org/10.1126/science.289.5482.1172
  5. Furusho, Y.; Hasegawa, H.; Tsuboi, A.; Kihara, N.; Takata, T. Chem. Lett. 2000, 18.
  6. Furusho, Y.; Oku, T.; Hasegawa, H.; Tsuboi, A.; Kihara, N.; Takata, T. Chem. Eur. J. 2003, 9, 2895. https://doi.org/10.1002/chem.200204644
  7. Oku, T.; Furusho, Y.; Takata, T. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 119. https://doi.org/10.1002/pola.10571
  8. Oku, T.; Furusho, Y.; Takata, T. Angew. Chem., Int. Ed. Engl. 2004, 43, 966. https://doi.org/10.1002/anie.200353046
  9. Diedrich, F.; Echegoyen, L.; Gomez-Lopez, M.; Kessinger, R.; Stoddart, J. F. J. Chem. Soc., Perkin Trans. 2: Phys. Org. Chem. 1999, 1577-1586.
  10. Oku, T.; Furusho, Y.; Takata, T. submitted to Macromolecules.
  11. Sutherland, I. O. Annu. Rep. NMR Spectrosc. 1971, 4, 71.
  12. Sandstrom, J. Dynamic NMR Spectroscopy; Academic Press: London, 1982.
  13. Dahlquist, F. W.; Longmur, K. J.; Du Vernet, R. B. J. Magn. Reson. 1975, 17, 406.
  14. Ben-David Blanca, M.; Maimon, E.; Kost, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 2216. https://doi.org/10.1002/anie.199722161
  15. Kelly, T. R.; Tellitu, I.; Sestelo, J. P. Angew. Chem., Int. Ed. Engl. 1997, 36, 1866. https://doi.org/10.1002/anie.199718661
  16. Leigh, D. A.; Murphy, A.; Smart, J. P.; Deleuze, M. S.; Zerbetto, F. J. Am. Chem. Soc. 1998, 120, 6458. https://doi.org/10.1021/ja974065m
  17. 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. https://doi.org/10.1002/(SICI)1521-3773(19980518)37:9<1294::AID-ANIE1294>3.0.CO;2-F

Cited by

  1. Fluorescence Control of Boron Enaminoketonate Using a Rotaxane Shuttle vol.15, pp.18, 2013, https://doi.org/10.1021/ol401984j
  2. Synthesis and Shuttling Behavior of Rotaxanes Consisting of Crown Ether Wheel and Disulfide Dumbbell with Two Ammonium Centers. vol.36, pp.12, 2005, https://doi.org/10.1002/chin.200512068
  3. Effect of Steric Barrier on the Shuttling of Rotaxane Having Crown Ether Wheel vol.36, pp.2, 2004, https://doi.org/10.1246/cl.2007.208