Abstract
Photoinduced electron transfer was studied in a supramolecular complex assembled by an electron-donating substrate (N-(1-naphthylacetyl)-1-adamantanamine (1)) and an electron-accepting receptor (p-nitrobenzoyl-β-cyclodextrin (NBCD)), which was stabilized by hydrophobic interactions in water/methanol (9 : 1) binary solvents. Fluorescence quenching results indicated that the electron transfer process occurred in a intra-supramolecular system. The electron transfer reactions of 1- or 2-naphthyl acetate with NBCD were also studied, and upward Stern-Volmer curves were obtained. It is concluded that two different electron transfer pathways, intra-supramolecular and inter-molecular electron transfer processes, exist.
Similar content being viewed by others
REFERENCES
G. L. Closs, M. D. Johnson, J. R. Miller and P. Piotrowiak, J. Am. Chem. Soc. 111, 3751 (1989).
D. Gust, T. A. Moore, A. L. Moore, S.-J. Lee, E. Bittersmann, D. K. Luttrull, A. A. Rehm, J. M. DeGraziano, X. C. Ma, F. Gao, R. E. Belfored and T. T. Trier, Science 248, 199 (1990).
C. Walsh, Acc. Chem. Res. 13, 148 (1980).
J.-M. Lehn, Supramolecular Chemistry: Concepts and Perspectives. VCH, Weinheim (1995).
P. J. F. de Rege, S. A. Williams and M. J. Therien, Science 269, 1409 (1995).
M. R. Arkin, E. D. A. Stemp, C. Turro, N. J. Turro and J. K. Barton, J. Am. Chem. Soc. 118, 2267 (1996).
B. König, M. Pelka, H. Zieg, T. Ritter, H. Bouas-Laurent, R. Bonneau and J.-P. Desvergne, J. Am. Chem. Soc. 121, 1681 (1999).
V. Y. Shafirovich, S. H. Courtney, N. Ya and N. E. Geactinov, J. Am. Chem. Soc. 117, 4920 (1995).
Y.-H. Wang, H.-M. Zhang, Z.-X. Liang, L. Liu, Q.-X. Guo, C.-H. Tung, Y. Inoue and Y.-C. Liu, J. Org. Chem. 67, 2429 (2002).
D. Rehm and A. Weller, Isr. J. Chem. 8, 259 (1970).
I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules. Academic Press, New York, NY (1971).
G. D. Santis, L. Fabbrizzi, M. Licchelli, A. Poggi and A. Taglietti, Angew. Chem. Int. Ed. Engl. 35, 202 (1996).
E. S. Psych and N. C. Yang, J. Am. Chem. Soc. 85, 2124 (1963).
M. Kropf, E. Joselevich, H. Dürr and I. Willner, J. Am. Chem. Soc. 118, 655 (1996).
Q. X. Guo, X. Q. Zheng, S. H. Luo and Y. C. Liu, Chin. Chem. Lett. 7, 357 (1996).
K. Harata, Bull. Chem. Soc. Jpn. 52, 1807 (1979).
R. I. Gelb, L. M. Schwartz and D. A. Laufer, J. Chem. Soc., Perkin Trans. 2, 15 (1984).
R. I. Gelb, L. M. Schwartz and D. A. Laufer, J. Chem. Soc., Perkin Trans. 2, 15 (1984).
P. Debye, Polar Molecules. Dover Publications, New York, NY (1945).
Rights and permissions
About this article
Cite this article
Wang, YH., Fu, Y., Zhu, MZ. et al. Photoinduced electron-transfer reactions in a host-guest assembly of mono-6-p-nitrobenzoyl-β-cyclodextrin with N-(1-naphthylacetyl)-1-adamantanamine. Research on Chemical Intermediates 29, 11–19 (2003). https://doi.org/10.1163/156856703321328370
Issue Date:
DOI: https://doi.org/10.1163/156856703321328370