Photochemical Transformation of Chalcone Derivatives

  • Published : 2001.03.01

Abstract

The photoisomerization behavior of benzylideneacetophenones, known as chalcones, was studied. We synthesized the chalcone derivatives that have ether groups at 4 and 4' positions. Due to the electron donating ability of the ether oxygen, the bond order of the single bond between two phenyl ring of the chalcone strengthened, which eventually increased the rotational barrier of the single bond. The rotational barrier of the single bond is about 20-22 kcal/mole. Thermal recovery of this process took about 1 min. The UV-visible spectra of these chromophores exhibit two characteristic absorption peaks at 276 nm and 340 nm. The relative intensity of the peaks varies depending on the alkyl chain length of the substituent. Photo-irradiation with the 365 nm light monotonously decreases the 340 nm peak. However, the photo-irradiation with 254 nm light induce two competing processes and produced rather complicated absorption profile.

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References

  1. The chemistry of chalcones and related compounds Dhar D.N.
  2. Spectrochimica Acta Part A v.55 Ab initio calculations of the absorption spectrum of chalcone Oumi M.;D. Maurice;M.H. Gordon
  3. Journal of Photochemistry and Photobiology v.A no.130 Spectrometric evidence for the existence of rotamers in solutions of some ketocyanine dyes Marcotte N.;S.F. Forgues
  4. Colloids and Surfaces v.A Synthesis and evaluation of the photo-sensitive polyimide containing the chalcone structure for the photoalignment in liquid crystal display Shin D.M.;D.M. Song
  5. Polymer v.40 Photocrosslinked polymers based on pendant extended chalcone as photosensitive moieties Rehab A;N. Salahuddin
  6. Chem. Rev. v.100 Photoalignment of liquid crystal systems Ichimura K.
  7. Liquid Crystals v.20 Command surfaces 15[1]. Photoregulation of liquid crystal alignment by cinnamoyl residues on a silica surface Tomita H.;K. Kudo;K. Ichimura
  8. IDW'97 New photo alignment materials containing chalcone structures Makita Y.;T. Ogawa;S.I. Kimura;S. Nakata;M. Kimura;Y. Matsuki;Y. Takeuchi
  9. Liquid Crystals v.27 Photoinduced orientation in poly(vinylcinnamate)and poly(7-methacryloyloxycoumarin)thin films and the consequences on liquid crystal alignment Perny S.;P.L. Barny
  10. Supramolecular Science v.3 Surface-assisted photo regulation of molecular assemblages as commander/soldier molecular systems Ichimura K.
  11. IEICE Trans. ELECTRON v.E79 Alignment Control of Liquid Crystal Molecules using Photo-dimerization Reaction of Poly(Vinyl Cinnamate) Iimura Y.;S. Kobayashi;T. Hashimoto;T. Sugiyama;K. Katoh
  12. Polymer v.40 Photoinduced alignment of polymer liquid crystals containing azobenzene moieties in the side chain. 4. Dynamic study of the alignment process Wu Y.;A. Kanazawa;T. Shiono;T. Ikeda;Q. Zhang