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Synthesis and Guest Binding Properties of Cyclophanes Containing Two Benzo[b]furan Rings

  • Published : 2004.11.20

Abstract

The cyclophanes 1a-d containing two benzo[b]furan rings connected by various bridges have been prepared and their binding behaviors with N-benzylphenethylammonium cation 2 were examined by NMR titration method. The successive alkylation reactions of 4-hydroxyl groups and then 2-hydroxyl groups of 2,4-dihydroxybenzophenonse gave macrocycles 5a-c. Photoirradiation of the macrocycles 5a-c with 350 nm mercury lamp followed by dehydration afforded the cyclophanes 1a-c. Hydrolysis of two ester groups pendant on a bridge of 1b produced the carboxyl group-containing cyclophane 1d. The cyclophane 1a having a p-xylene bridge showed 1 : 1 binding with 2 with the binding constant of $36{\pm}6M^{-1}$ in 3 : 1 $CDCl_3$/methanol-$d_4$ solvent, while 1b and 1c which have neutral flexible bridges exhibited no appreciable binding with 2. The disodium salt of 1d showed much higher binding affinity for 2 forming 1 : 1 and 1 : 2 complexes.

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References

  1. Breitenbach, J.; Boosfeld, J.; Vogtle, F. In Comprehensive Supramolecular Chemistry; Vogtle, F., Ed.; Elsevier Science: 1996; Vol. 2, pp 29-67.
  2. Vogtle, F. Cyclophane Chemistry; Wiley: Chichester, 1993.
  3. Park, K. K.; Seo, H.; Kim, J.-G.; Suh, I.-H. Tetrahedron Lett. 2000, 41, 1393. https://doi.org/10.1016/S0040-4039(99)02300-X
  4. Park, K. K.; Han, I. K.; Park, J. W. J. Org. Chem. 2001, 66, 6800. https://doi.org/10.1021/jo0103165
  5. Park, K. K.; Lim, H.; Kim, S.-H.; Bae, D. H. J. Chem. Soc. Perkin Trans. 1 2002, 310.
  6. Park, K. K.; Lim, H. Heterocycles 2002, 57, 657. https://doi.org/10.3987/COM-02-9446
  7. Abdul-Aziz, M.; Auping, J. V.; Meador, M. A. J. Org. Chem. 1995, 60, 1303. https://doi.org/10.1021/jo00110a038
  8. Lappin, G. R.; Zannucci, J. S. J. Org. Chem. 1971, 36, 1808. https://doi.org/10.1021/jo00812a019
  9. Sumathi, T.; Balasubramanian, K. K. Tetrahedron Lett. 1992, 33, 2213. https://doi.org/10.1016/0040-4039(92)88180-D
  10. Sharshira, E. M.; Okamura, M.; Hasegawa, E.; Horaguchi, T. J. Heterocyclic Chem. 1997, 34, 861. https://doi.org/10.1002/jhet.5570340325
  11. Sharshira, E. M.; Horaguchi, T. J. Heterocyclic Chem. 1997, 34, 1837. https://doi.org/10.1002/jhet.5570340634
  12. Wagner, P. J. Acc. Chem. Res. 1989, 22, 83. https://doi.org/10.1021/ar00159a001
  13. Wagner, P. J.; Meador, M. A.; Scaiano, J. C. J. Am. Chem. Soc. 1984, 106, 7988. https://doi.org/10.1021/ja00337a066
  14. Physical Methods in Supramolecular Chemistry; Davies, J. E. D., Ripmeester, J. A., Eds.; Comprehensive Supramolecular Chemistry; Pergamon: 1996; Vol. 8, pp 428-435.
  15. Park, K. K.; Lim, H. S.; Park, J. W. Bull. Korean Chem. Soc. 1999, 20, 211.

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  2. Synthesis and Guest Binding Properties of Cyclophanes Containing Two Benzo[b]furan Rings. vol.36, pp.13, 2005, https://doi.org/10.1002/chin.200513063