Fluorescence sensing due to allosteric switching of pyrene functionalized cis-cyclohexane-1,3-dicarboxylate

Abstract

The excimer/monomer fluorescence ratio for a pyrene functionalized cis-cyclohexane-1,3-dicarboxylate decreases upon titration with divalent and monovalent metal cations, as well as strong and weak acids.

References

1. H.-J. Schneider and A. K. Mohammad-Ali, in Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. D. Davies, D. D. MacNicol and F. Vögtle, Pergamon, New York, 1996, vol. 2, pp. 81–86.
2. G. L. Arnold and S. A. van Arman, Tetrahedron Lett., 1997, 38, 4745; G. E. Collins and L.-S. Choi, Chem. Commun., 1997, 1135; H. Matsumoto and S. Shinkai, Tetrahedron Lett., 1996, 37, 77; M. Takeshita and S. Shinkai, Chem. Lett., 1994, 125; I. Aoki, T. Harada, T. Sakaki, Y. Kawahara and S. Shinkai, J. Chem. Soc., Chem. Commun., 1992, 1341.
3. G. K. Walkup and B. Imperiali, J. Am. Chem. Soc., 1996, 118, 3053; H. Ikeda, M. Nakamura, N. Ise, N. Oguma, A. Nakamura, T. Ikeda, F. Toda and A. Ueno, J. Am. Chem. Soc., 1996, 118, 10 980.
4. Other switchable cyclohexane-based systems include the following: V. V. Samoshin, V. A. Chertkov, L. P. Vatlina, E. K. Dobretsova, N. A. Simonov, L. P. Kastorsky, D. E. Gremyachinsky and H.-J. Schneider, Tetrahedron Lett., 1996, 37, 3981; M. Goodall, P. M. Kelly, D. Parker, K. Gloe and H. Stephan, J. Chem. Soc., Perkin Trans. 2, 1997, 59; S. M. Shirdkar and G. R. Weisman, J. Chem. Soc., Chem. Commun., 1989, 236.
5. D. S. Kemp and K. S. Petrakis, J. Org. Chem., 1981, 46, 5140.
6. F. M. Menger, P. A. Chicklo and M. J. Sherrod, Tetrahedron Lett., 1989, 30, 6943.
7. K. Izutsu, Dissociation Constants in Dipolar Aprotic Solvents, Blackwell Scientific Publications, Oxford, 1990.
8. I. M. Kolthoff, M. K. Chantooni and S. Bhowmik, J. Am. Chem. Soc., 1968, 90, 23.
9. I. M. Kolthoff and M. K. Chantooni, J. Am. Chem. Soc., 1975, 97, 1376.