Advertisement

Inclusion and Reaction Chemistry of Two Anthracene-Appended γ-Cyclodextrins

  • Akihiko Ueno
  • Fumio Moriwaki
  • Akiko Azuma
  • Tetsuo Osa

Summary

The anthracene moieties of regioisomers of 6A,6X-bis(anthracene-9-carbonyl)-γ-cyclodextrins undergo photodimerization, affording a trans photodimer for AC, AD, and AE isomers and a cis photodimer for the AB isomer. The photodimers of the AD and AE isomers were stable, but those of AB and AC were unstable, returning to the original anthracene monomers. The dissociation of the photodimers was suggested to be due to the inherent instability of the cis photodimer of the AB isomer and the strain-rich nature of the trans photodimer of the AC isomer. The photodimerization followed by hydrolysis of 6A,6X-bis-(anthracene-1-carbonyl)-γ-cyclodextrins afforded four photodimers of 1-anthracenecarboxylic acid, the relative yields of the photodimers being controlled by the locations of the anthracene moieties in the regioisomers. These results demonstrate that the γ-cyclodextrin template method is useful to make chemical reactions proceed stereoselectively as well as to produce new photochrome systems.

Keywords

Circular Dichroism Photochromic Behavior Guest Binding Naphthyl Moiety Anthracene Moiety 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Ueno, A.; Takahashi, K.; Osa, T. J. Chem. Soc., Chem. Commun. 1980, 921Google Scholar
  2. 2.
    Ueno, A; Moriwaki, R; Osa, T.; Hamada, F.; Murai, K. Tetrahedron 1987,43, 1571CrossRefGoogle Scholar
  3. 3.
    Ueno, A.; Tomita, Y.; Osa, T. J. Chem. Soc., Chem. Commun. 1983, 976Google Scholar
  4. 4.
    Ueno, A; Moriwaki, F.; Osa, T.; Hamada, F.; Murai, K. Bull. Chem. Soc. Jpn. 1986, 59, 465CrossRefGoogle Scholar
  5. 5.
    Ueno, A; Moriwaki, F.; Osa, T.; Hamada, F.; Murai, K. J. Am. Chem. Soc. 1988, 110, 4323CrossRefGoogle Scholar
  6. 6.
    Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433.CrossRefGoogle Scholar

Copyright information

© Plenum Press, New York 1990

Authors and Affiliations

  • Akihiko Ueno
    • 1
  • Fumio Moriwaki
    • 1
  • Akiko Azuma
  • Tetsuo Osa
    • 1
  1. 1.Pharmaceutical InstituteTohuko UniversitySendaiJapan

Personalised recommendations