Photoinduced Electron Transfer in Host-Guest Complexes of 2-Naphthyl-O(CH2) n -adamantanamines with Mono-6-O-p-nitrobenzoyl-β-cyclodextrin and Mono-6-O-m-nitrobenzoyl-β-cyclodextrin

  • HUI-YUAN HU
  • MAN-ZHOU ZHU
  • ZHI-PING ZHANG
  • GUO-TAO WEN
  • QING-XIANG GUO
Article
First Online:

Abstract

A number of naphthalene derivatives containing adamantanamine binding moiety and an (CH2) n (n=2, 3, 4, 5, 6) spacer were prepared as the electron donor. A supramolecular assembly was fabricated by the inclusion between the donor substrates and the host molecules, i.e., mono-6-O-p-nitrobenzoyl-β-cyclodextrin (pNBCD) and mono-6-O-m-nitrobenzoyl-β-cyclodextrin (mNBCD), in water. The fluorescence quenching in these systems was studied in detail. It revealed efficient photoinduced electron transfers (PET) between the naphthalene donors and the cyclodextrin acceptors. This PET process was partitioned into a dynamic quenching component caused by bimolecule collision reactions and a static quenching component due to hydrophobic binding between the donor and acceptor molecules. Detailed Stern–Volmer constants were measured and they were partitioned into dynamic Stern–Volmer quenching constants (dynamic quenching) and static binding constants (static quenching). In these two pathways, the static quenching was found to be highly efficient and dominant in the presence of NBCD.

Key words

cyclodextrin fluorescence quenching photoinduced electron transfer supramolecule 
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

Acknowledgement

We thank NSFC for the financial support (No 20332020 and 20472079).

Reference

  1. 1.
    (a) J. Deisenhofer and H. Michel: Angew. Chem. Int. Ed. Engl. 28, 829 (1989); (b) R. Huber: Angew. Chem. Int. Ed. Engl. 28, 848 (1989); (c) M.R. Wasielewski: Chem. Rev. 92, 435 (1992); (d) V.K. Yachandra, K. Sauer, and M. P. Klein: Chem. Rev. 96, 2927 (1996); (e) C.H. Tung, L.Z. Wu, and L.P. Zhang: Chin. J. Org. Chem. 21, 784 (2001); (f) L. Sun, L. Hammarstrom, B. Akermark, and S. Btyring: Chem. Soc. Rev. 30, 36 (2001)Google Scholar
  2. 2.
    (a) M.D. Newton and N. Sutin : Annu. Rev. Phys. Chem. 35, 437 (1984); (b) R.A. Marcus and N. Sutin: Biochim. Biophys. Acta 811, 265 (1985); (c) K.V. Mikkelsen and M.A. Ratner: Chem. Rev. 87, 113 (1987); (d) T. Ito, T.Ujiie, M. Naka, and H. Nakamure: Chem. Phys. Lett. 340, 308 (2001); (e) R.A. Marcus: Agew. Chem. Int. Ed. Engl. 32, 1111 (1993)Google Scholar
  3. 3.
    (a) S. Speciser: Chem. Rev. 96, 1953 (1996); (b) E. David, R. Born, E. Kaganer, E. Joselevich, H. Durr, and I. Willner: J. Am. Chem. Soc. 119, 7778 (1997); (c) V. Balzani, S. Campagna, G. Denti, A. Juris, S. Serroni, and M. Venturi: Acc. Chem. Res. 31, 26(1998); (d) X.Y. Yi, L.Z. Wu, and C.H. Tung: J. Phys. Chem. 104, 9468 (2000); (e) W. Liu, Z.X. Zhou, F.Y. Wang, and Z.Y. Zhang: Acta Chim. Sin. 59, 629 (2001); (f) Z. Zhou, W. Liu, F. Wang, and Z. Zhang: Science in China C 44, 241 (2001)Google Scholar
  4. 4.
    (a) 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); (b) H. Tsue, H. Imahori, T. Kaneda, Y. Tanaka, T. Okada, K. Tamaki, and Y. Sakata: J. Am. Chem. Soc. 122, 2279 (2000); (c) J. Sun, Y. Liu, D.W. Cheng, Q.Y. Zhang, F.Y. Li, Y.L. Li, D.B. Zhu, L.B. Gan, and C.H. Huang: Acta Chim. Sin. 58, 786 (2000); (d) H. Jiang and H. Xu: J. Chin. Chem. Lett. 11, 767 (2000); (e) C.S. Rajesh, G.J. Capitosti, S.J. Cramer, and D.A. Modarelli: J. Phys. Chem. B 105, 10175 (2001); (f) K. Ban, T. Veki, Y. Tamada, T. Saito, S.-I. Imabayshi, and M. Watanabe: Electrochem. Commun. 3, 649 (2001); (g) M. Lor, J. Thielemans, L. Viaene, M. Cotlet, J. Hofkens, T. Weil, C. Hampel, K. Mullen, J.W. Verhoeven, M. Van der Auweraer, and F.C. De Schryver: J. Am.Chem. Soc. 124, 9918 (2002); (h) R. Ballardini, V. Balzani, M. Clemente-Leon, A. Credi, M.T. Gandolfi, P.J. Elena, J.F. Stoddart, and H.R. Tseng: J. Am. Chem. Soc. 124, 12786 (2002); (i) S. Fukuzumi, J. Okamoto, Y. Yoshida, H. Imahori, Y. Araki, and O. Ito: J. Am. Chem. Soc. 125, 1007 (2003); (j) H.P. Zhang, Y.L. Zhou, M.H. Zhang, T. Shen, Y.L. Li, and D.B. Zhu: Chem. J. Chin. Univ. 24, 492 (2003); (k) H.-B. Yi, X.-H. Duan, X.-Y. Li, and S.-Y. Yang: Chem. J. Chin. Univ. 24, 1438 (2003)Google Scholar
  5. 5.
    (a) D. Gust and T.A. Moore: Top. Curr. Chem. 159, 103 (1991); (b) D. Gust and T.A. Moore: Science 244, 35 (1989); (c) T.A. Moore, D. Gust, A.L. Moore, R.V. Bensasson, P. Seta, E. Bienvenue: In V. Balzani (ed.), Supramolecular Photochemistry, D. Reidel, Boston (1987) p. 283; (d) D. Gust and T.A. Moore, In V. Balzani (ed.), Supramolecular Photochemistry; D. Reidel: Boston (1987), p.␣267; (e) M.R. Wasielewski, G.L. Gains, III, G.P. Wiederrecht, W.A. Svec, and M.P. Niemczyk: J. Am. Chem. Soc. 115, 10442 (1993); (f) G.M. Sanders, M. van Dijk, A. van Veldhuizen, and M.J. van der Plas: J. Chem. Soc., Chem. Commun. 1311 (1986); (g) M.R. Wasielewski, M.P. Niemczyk, W.A. Svec, and E.B. Pewitt: J. Am. Chem. Soc. 107, 5562 (1985); (h) S.L. Mecklenburg, B.M. Peek, B.W. Erickson, and T.J. Meyer: J. Am. Chem. Soc. 109, 3297(1987); (i) E. Danielson, C.M. Elliott, J.W. Mesket, and T.J. Meyer: J. Am. Chem. Soc. 109, 2519 (1987); (j) D.G. Johnson, M.P. Niemczyk, D.W. Minsek, G.P. Widerrecht, W.A. Svec, G.L. Gaines, III, and M.R. Wasielewski: J. Am. Chem. Soc. 115, 5692 (1993)Google Scholar
  6. 6.
    (a) H. Kurreck and M. Huber: Angew. Chem., Int. Ed. Engl. 34, 849 (1995); (b) D. Gust, T.A. Moore, A.L. Moore, S.-J. Lee, E. Bittersmann, D.K. Luttrull, A.A. Rehms, J. M. DeGraziano, J. M. DeGraziano, X.C. Ma, F. Gao, R.E. Belfored, and T.T. Trier: Science. 248, 199 (1990) Google Scholar
  7. 7.
    (a) C. Walsh, J. Fisher, R. Spencer, D.W. Graham, W.T. Ashton, J.E. Brown, R.D. Brown, and E.F. Rogers: Biochemistry 17, 1942 (1978); (b) C. Walsh: Acc. Chem. Res. 13, 148 (1980)Google Scholar
  8. 8.
    (a) R. Breslow and S. Chung: J. Am. Chem. Soc. 112, 9659 (1990); (b) B. Zhang and R. Breslow: J. Am. Chem. Soc. 115, 9353 (1993); (c) W.-Q. Tong, J.L. Lach, T.F. Chin, and J.K. Guillory: J.␣Pharm. Biomed. Anal. 9, 1139 (1991); (d) Y. Inoue, Y. Liu, L.-H.Tong, B.-J. Shen, and D.-S. Jin: J. Am.Chem. Soc. 115, 10637 (1993); (e) H. Ikeda, M. Nakamura, N. Ise, N. Oguma, A. Nakamura, T. Ikeda, F. Toda, and A. Ueno: J. Am. Chem. Soc. 118, 10980 (1996); (f) A. Matsushita, T. Kuwabara, A. Nakamura, H. Ikeda, and A. Ueno: J. Chem. Soc., Perkin Trans. 2 1705 (1997)Google Scholar
  9. 9.
    (a) Y. Kuroda, M. Ito, T. Sera, and H. Ogoshi: J. Am. Chem. Soc. 115, 7003 (1993); (b) V.Y. Shafirovich, S.H. Courtney, N. Ya, and N.E. Geactinov: J. Am. Chem. Soc. 117, 4920 (1995)Google Scholar
  10. 10.
    (a) K.A. Connors: Chem. Rev. 97, 1325 (1997); (b) Y. Liu and C.C. You: Chin. J. Chem. 19, 533 (2001); (c) L. Liu and Q.X. Guo: J. Incl. Phenom. 42, 1 (2002)Google Scholar
  11. 11.
    (a) K. Uekama, F. Hirayama, and T. Irie: Chem. Rev. 98, 2045 (1998); (b) B. Tang, L. Ma, and H. Wang: Chin. J. Anal. Chem. 30, 482 (2002)Google Scholar
  12. 12.
    (a) R. Breslow, Acc. Chem. Res. 28, 146 (1995); (b) F. Cao, Y. Ren, W.-Y. Hua, K.-F. Ma, and Y.-L. Guo: Chin. J. Org. Chem. 22, 827 (2002)Google Scholar
  13. 13.
    (a) A.P. Croft and R.A. Bartsch: Tetrahedron 39, 1417 (1983); (b) A.R. Khan, P. Forgo, K.J. Stine, and V.T. D’Souza: Chem. Rev. 98, 1977 (1998)Google Scholar
  14. 14.
    (a) R. Breslow and S. Chung: J. Am. Chem. Soc. 112, 9659 (1990); (b) B. Zhang and R. Breslow: J. Am. Chem. Soc. 115, 9353 (1993); (c) W.-Q. Tong, J.L. Lach, T.F. Chin, J.K. Guillory: J. Pharm.Biomed. Anal. 9, 1139 (1991); (d) Y. Inoue, Y. Liu, L.-H. Tong, B.-J. Shen, and D.-S. Jin, J. Am. Chem. Soc. 115, 10637 (1993); (e) H. Ikeda, M. Nakamura, N. Ise, N. Oguma, A. Nakamura, T. Ikeda, F. Toda, and A. Ueno: J. Am. Chem. Soc. 118, 10980 (1996); (f) A. Matsushita, T. Kuwabara, A. Nakamura, H. Ikeda, and A. Ueno: J. Chem. Soc., Perkin Trans. 2 1705 (1997)Google Scholar
  15. 15.
    Nelissen H.F.M., Kercher M., De Cola L., Feiters M.C., Nolte R. (2002) J. M. Chem. Eur. J. 8: 5407CrossRefGoogle Scholar
  16. 16.
    Park J.W., Song H.E., Lee S.Y. (2002) J. Phys. Chem. B. 106: 7186CrossRefGoogle Scholar
  17. 17.
    (a) Y.-H. Wang, H.-M. Zhang, L. Liu, Z.-X. Liang, Q.-X. Guo, C.-H. Tung, Y. Inoue, and Y.-C. Liu: J. Org. Chem. 67, 2429 (2002); (b) Y.-H. Wang, M.-Z. Zhu, X.-Y. Ding, J.-P. Ye, L. Liu, and Q.-X. Guo: J. Phys. Chem. B 107, 14087 (2003)Google Scholar
  18. 18.
    (a) T. Morii, T. Tanaka, S.-I. Sato, M. Hagihara, Y. Aizawa, and K. Makino: J. Am. Chem. Soc. 124, 180 (2002); (b) L.-X. Song, X.-K.␣Ke, and Z.-J. Guo: Acta Chim. Sin. 60, 1419 (2002)Google Scholar
  19. 19.
    Rehm D., Weller A. (1970) Isr. J. Chem. 8:259Google Scholar
  20. 20.
    (a) C.H. Evans, M. Partyka, and J. Van Stam: J. Inclusion. Phenom. 38, 381 (2000); (b) X.-Y. Sun, Z.-C. Wen, and Y.-B. Jiang: Chin. J. Chem. 21, 1335 (2003)Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • HUI-YUAN HU
    • 1
  • MAN-ZHOU ZHU
    • 1
  • ZHI-PING ZHANG
    • 1
  • GUO-TAO WEN
    • 1
  • QING-XIANG GUO
    • 1
  1. 1.Department of ChemistryUniversity of Science and Technology of ChinaHefeiP. R. China

Personalised recommendations