Journal of Photoscience

Korean Society of Photoscience (한국광과학회)
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PHOTOPHYSICAL PROPERTIES OF FLUORENONES WITH CHIRAL SUBSTITUENTS AND THEIR ASYMMETRIC RECOGNITION THROUGH INTERMOLECULAR HYDROGEN BONDING INTERACTIONS IN THE EXCITED STATES

  • Aikawa, Yoshihide (Department of Applied Chemistry, Graduate Course of Engineering, Tokyo Metropolitan University) ;
  • Shimada, Tetsuya (Department of Applied Chemistry, Graduate Course of Engineering, Tokyo Metropolitan University) ;
  • Tachibana, Hiroshi (Department of Applied Chemistry, Graduate Course of Engineering, Tokyo Metropolitan University) ;
  • Inoue, Haruo (Department of Applied Chemistry, Graduate Course of Engineering, Tokyo Metropolitan University)
  • Published : 1999.12.01
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Abstract

Asymmetric recognition of chiral alcohol by fluorenone derivatives with chiral substituents through intermolecular hydrogen bonding interaction in the singlet excited state was attempted. 1-((1S, 2R, 5S)-(+)-Menthyloxycarbonyl)aminofluoren-9-one (1-MAF) and 1-((1S, 2R, 5S)-(+)-menthyloxycarbonyl)oxyfluoren-9-one (1-MOF) were synthesized and their photophysical behaviors were characterized by the measurement of absorption and fluorescence spectra, as well as the quantum yield and the lifetime of fluorescence. The excited singlet states of 1-MAF and 1-MOF were revealed to have characteristics similar to those of fluorenone, though the intramolecular CT nature was fairly suppressed as compared with 3- and 4-substituted aminofluorenones. Fluorescences of 1-MAF and 1-MOF in acetonitrile were quenched by the addition of alcohols. Differences in fluorescence quenching efficiency were hardly observe for rather small chiral alcohols such as (R)-(-)- or (S)-(+)-2-butanol, while bulky alcohols such as menthol and isopinocampheol showed chiral recognition effects in their fluorescence quenching of 1-MAF in either acetonitrile or butyronitrile.

Keywords

References

  1. Chem. Rev. v.83 Asymmetric photochemistry in solution H. Rau
  2. Chem. Rev. v.92 Asymmetric photochemical reactions in solution Y. Inoue
  3. J. Org. Chem. v.57 Enantiodifferentiating Z-E photoisomerization of cyclooctene sensitized by chiral polyalkyl benzenepolycarboxylates Inoue, Y.;Yamasaki, N.;Yokoyama, T.;Tai, A.
  4. J. Org. Chem. v.58 Highly enantiodifferentiating photoisomerization of cyclooctene by congested and/or triplet-forming chiral sensitizers Inoue, Y.;Yamasaki, N.;Yokoyama, T.;Tai, A.
  5. J. Chem. Soc., Chem. Commun. Asymmetric cis-trans photoisomerization of cyclooctene sensitized by chiral aromatic esters Inoue Y.;Kunitomi Y.;Takamuku S.;Sakurai H.
  6. J. Chem. Soc., Perkin Trans. no.2 Singlet photoisomerization of simple alkene. part 1. cis-trans-photoisomerization of cyclooctene sensitized by aromatic esters 1 Inoue, Y.;Takamuku, S.;Kunitomi, Y.;Sakurai, H.
  7. J. Am. Chem. Soc. v.111 Temperature switching of product chirality upon photosensitized enantiodifferentiating cis-trans isomerization of cyclooctene Inoue, Y.;Yokoyama, T.;Yamasaki, N.;Tai, A.
  8. J. Am. Chem. Soc. v.120 Pressure and temperature control of product chirality in asymmetric photochemistry, enantiodifferentiating photoisomerization of cyclooctene sensitized by chiral benzenepolycarboxylates Inoue, Y.;Matsushima, E.;Wada, T.
  9. J. Am. Chem. Soc. v.119 Optically active (E, Z)-1,3-cyclooctadiene: First enantioselective synthesis through asymmetric photosensitization and chiroptical property Inoue, Y.;Tsuneishi, H.;Hakushi, T.;Tai, A.
  10. J. Chem. Soc. Perkin Trans. no.2 Enantiodifferentiating photoisomerization of 1-methylcyclooct-1-ene sensitized by chiral alkyl benzenecarboxylates: Steric effects upon stereodifferentiation Tsuneishi, H.;Hakushi, T.;Tai, A.;Inoue Y.
  11. J. Chem. Soc. Perkin. Trans. no.2 Direct and sensitized geometrical photoisomerization of 1-methylcyclooctene Tsuneishi, H.;Inoue, Y.;Hakusho, T.;Tai, A.
  12. Nature v.341 An optical yield that increases with temperature in a photochemically induced enantiomeric isomerization Inoue, Y.;Yokoyama, T.;Yamasaki, N.;Tai, A.
  13. J. Am. Chem. Soc. v.102 Chiral discrimination in excimer formation Tran, C. D.;Flender, J. H.
  14. J. Am. Chem. Soc. v.100 Steric effect on flurescence quenching of 1,1'-binaphthyl by chiral amines Irie, M.;Yorozu, T.;Hayashi, K.
  15. J. Am. Chem. Soc. v.103 Chiral discrimination in fluorescence quenching Yorozu, T.;Hayashi, K.;Irie, M.
  16. J. Am. Chem. Soc. v.111 Photophysical recognition of chiral surfaces Avnir, D.;Wellner, E.;Ottolenghi, M.
  17. J. Am. Chem. Soc. v.102 Photophysical investigations of chiral recognition in crown ethers Tundo, P.;Fendler, J. H.
  18. Tetrahedron Lett. Enantiotropic interactions in the fluorescence quenching of camphor by chiral amines Fox, M. A.;Singletary, N. J.
  19. J. Chem. Soc. Chem. Commun. Generation of optical activity by photoinduced chiroselective electron transfer Porter, G. B.;Sparks, R. H.
  20. J. Phys. Chem. v.82 Charge separation in photoinitiated electron transfer reaction induced by a polyelectrolyte Meyerstein, D.;Rabani, J.;Matheson, M. S.;Meisel, D.
  21. J. Phys. Chem. v.89 Photoinduced electron-transfer reactions between optical isomers Kaizu, Y.;Mori, T.;Kobayashi, H.
  22. Chem. Lett. Enantioselective electron transfer reaction catalyzed by a novel photosensitizer, $[Ru(S(-)\;or\;R(+)-phEtbpy)_3]^{2+}$ Ohkubo, K.;Ishida, H.;Hamada, T.;Inaoka, T.
  23. Fundamentals of Photoinduced Electron Transfer Kavarnos, G. J.
  24. J. Phys. Chem. Soc. v.86 Picoseond fluorescence lifetime of anthraquinone derivatives, Radiationless deactivation via intra- and intermolecular hydrogen bonds Inoue, H.;Hida, M.;Nakashima, N.;Yoshihara, K.
  25. J. Phys. Chem. A v.102 Photophysical properties of intramolecular chargetransfer exicited singlet state of aminofluorenone derivatives Yatsuhashi, T.;Nakajima, Y.;Shimada, T.;Inoue, H.
  26. J. Phys. Chem. A v.103 Effects of molecular structure and hydrogen bonding on the radiationless deactivation of singlet excited fluorenone derivatives Biczok, L.;Berces, T.;Inoue, H.
  27. J. Phys. Chem. A v.101 Molecular mechanism of radiationless deactivation of aminoanthraquinones through intermolecular hydrogen-bonding interaction with alcohols and hydroperoxides Yatsuhashi, T.;Inoue, H.
  28. J. Phys. Chem. A v.102 Molecular mechanism for the radiationless deactivation of the intramolecular charge-transfer excited singlet state of aminofluorenones through hydrogen bonds with alcohols Yatsuhashi, T.;Nakajima, Y.;Shimada, T.;Tachibana, H.;Inoue, H.
  29. Tetrhedron Lett. Fluorenone fluorescence Monroe, B. M.;Groff, R. P.
  30. Tetrahedron Lett. The quenching of fluorenone fluorescence by triethylamine. Medium effects on the singlet lifetime Caldwell, R. A.
  31. Bull. Chem. Soc. Jpn. v.69 Fujii, T.;Sano, M.;Mishima, S.;Hiratsuka, H.