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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
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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 761: Symposia B/C/D/F/G/NN – Molecular Electronics , 2002 , NN4.4/J7.4
Copyright
Copyright © Materials Research Society 2003

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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