Hostname: page-component-78c5997874-fbnjt Total loading time: 0 Render date: 2024-11-17T15:14:31.274Z Has data issue: false hasContentIssue false
  • English
  • Français

Semi-Empirical Study of a pH-Switchable [2] Rotaxane

Published online by Cambridge University Press:  11 February 2011

Laura Frankfort  and
Karl Sohlberg
Laura Frankfort
Affiliation:
Department of Chemistry, Drexel University, 3141 Chestnut Street, Philadelphia, PA, 19104
Karl Sohlberg
Affiliation:
Department of Chemistry, Drexel University, 3141 Chestnut Street, Philadelphia, PA, 19104
Get access

Abstract

Semi-empirical (AM1) electronic structure calculations are reported on a pH-switchable [2] rotaxane whose synthesis was reported in [Angew. Chem. Int. Ed., 36 (1997) 1904]. The [2] rotaxane possesses two cationic binding sites, with different affinities toward dibenzo [24] crown-8 (the ring component of the [2] rotaxane) depending upon the pH of the system. The computational results capture this pH-sensitive bistability, the key device-like characteristic of the rotaxane.

Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 741: Symposium J – Nano- and Microelectromechanical Systems (NEMS and MEMS) and Molecular Machines , 2002 , J7.4
Copyright
Copyright © Materials Research Society 2003

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

[1] Raymo, F.M. and Stoddart, J.F., Chem. Rev. 99, 1643 (1999).Google Scholar
[2] Balzani, V., Gomez-Lopez, M. and Stoddart, J.F., Acc. Chem. Res. 31, 405 (1998).Google Scholar
[3] Anelli, P.L., Spencer, N. and Stoddart, J.F., J. Am. Chem. Soc. 113, 5131 (1991).Google Scholar
[4] Martinez-Diaz, M.-V., Spencer, N. and Stoddart, J.F., Angew. Chem. Int. Ed. Engl. 36, 1904 (1997).Google Scholar
[5] Dewar, M.J.S., Zoebisch, E.G., Healy, E.F. and Stewart, J.J.P., J. Am. Chem. Soc. 107, 3902 (1985).Google Scholar
[6] Levine, I.N., Quantum Chemistry (Prentice-Hall, Englewood Cliffs, NJ, 1991), chapter 17.Google Scholar
[7] Buemi, G., Zuccarello, F. and Raudino, A., J. Mol. Struct. (Theochem) 164, 379 (1988).Google Scholar
[8] Allinger, N.L., J. Am. Chem. Soc. 99, 8127 (1977).Google Scholar
[9] Hyperchem™ Release 6.02 for Windows™. Copyright 2000 by Hypercube Inc. 419 Phillip Street, Waterloo, Ontario, Canada N2L3X2.Google Scholar
[10] Schmidt, M.W., Baldridge, K.K., Boatz, J.A., Elbert, S.T., Gordon, M.S., Jensen, J.H., Koseki, S., Matsunga, N., Nguyen, K.A., Su, S.J., Windus, T.L., Dupuis, M. and Montgomery, J.A., J. Comput. Chem. 14, 1347 (1993).Google Scholar
[11] Ricketts, H.G., Stoddart, J.F. and Hann, M.M., in Computational Approaches in Supramolecular Chemistry, edited by Wipff, G. (Kluwer Academic Publishers, Dordrecht, 1994), p. 377.Google Scholar
[12] Weast, R.C. (Editor), CRC Handbook of Chemistry and Physics, 57th ed. (CRC Press, Cleveland, 1976–1977), p. F–216.Google Scholar