Journal of Photoscience

Korean Society of Photoscience (한국광과학회)
권호 표지

"KALEIDOSCOPIC" TOPOCHEMICAL PHOTOPOLYMERIZATION BEHAVIOR OF DIOLEFIN COMPOUNDS

  • Published : 1997.09.01
Download PDF
⟨ Previous Next ⟩

Abstract

INTRODUCTION : Various types of organic reactions in the crystalline state, so-called "topochemical reaction", have been reported in this century." Among the reactions, [2+2] photocycloaddition of diolefin crystals are one of the most intensively investigated examples. In the topochemical reaction in a pure sense, the space group symmetry is perfectly preserved throughout the reaction as were demonstrated by the crystalline-state photopolymerization of 2,5-distyrylpyrazine (2,5-DSP) and photodimerization of propyl $\alpha$-cyano-4-[2-(4-pyridyl) ethenyl]cinnamate. 2,5-DSP was initially prepared by Franke and in 1958 Koelsch and Gumprecht described briefly in their article of diazine-derivatives that it was found that the compound (2,5-DsP) was converted into a colorless insoluble polymer (\ulcorner) dec. 331~331$\circ$ when the solid was exposed for a few hours to ultraviolet light. Wright described in his book as if Koelsch and Gumprecht had investigated both the structure of the photoproduct and the crystal structure 2,5-DSP in detail. However, in the paper, they have not described any study on chemically correct analysis and crystallography of the resulting photoproduct at all. In 1967, one of present authors (M. H.) independently made the same observation as Franke that brilliant yellow crystal of 2,5-DSP was converted into powdery white substance under the sunlight in the course of a preparative study of pyrazine-2,5-dicarboxylic acid from 2,5-DSP. He investigated this phenomenon and concluded for the first time that a linear highmolecular-weight polymer crystal ([$\eta$] > 3.0 in $CF_3COOH$ solution) with recurring cyclobutane units in the main chain, had been produced from 2,5-DSP crystal by the action of sunlight.on of sunlight.

Keywords

References

  1. Photochemistry in Organized and Constrained Media Ramamurthy, V.
  2. Mol. Cryst. Liq. Cryst. v.30 Photodimerization and photopolymerization Organic Chemistry For recent reviews, see: Hasegawa, M.
  3. Mol. Cryst. Liq. Cryst. v.219 Kaleidoscopic photochemical behavior of unsymmetric diolefin crystals Hasegawa, M.;Y. Hashimoto
  4. J. Polym. Sci. v.A2 10 Four-center type photopolymerization in the crystalline state. V. X-Ray crystallographic study of the polymerization of 2,5-distyryl-pyrazine Nakanishi, H.;M. Hasegawa;Y. Sasada
  5. J. Photochem. Photobiol., A, Chem v.41 Topochemical photopolymerization of unsymmetrically substituted diloefinsi. Topochemical [2+2]photopolymerization of n-propyl α-cyano-4-[2(4-pyridyl) ethenyl]cinnamate Hasegawa, M.;S. Kato;K. Saigo;S. R. Wilson;C. L. Stern;I. C. Paul
  6. Chem. Ber. v.38 Kondensation des 2,5-dimethyl-pyrazins mit salicylaldehyd zu 2-o-oxycinnamethyl-5-methylpyrazin Franke, R.
  7. J. Org. Chem. v.23 Some diazine-N-oxides Koelsch, C. F.;W. H. Cumprecht
  8. Molecular Crystals Wright, J. D.
  9. Polym. Lett. v.B5 Four-center type photopolymerization in the solid state. Poly-2,5-distyrylpyrazine Hasegawa, M.;Y. Suzuki
  10. J. Polym. Sci., Phys. Ed. v.16 Four-center type photopolymerization. A heterogeneous topochemical solid-state reaction Meyer, W.;G. Lieser;G. Wegner
  11. Polym. Lett. v.17 On the space group of poly-2,5-distyrylpyrazine Nakanishi, H.;Y. Sasada;M. Hasegawa
  12. J. Am. Chem. Soc. v.115 Structural and lattice dynamical investigation of models for reaction in organic crystals Stezowski, J. J.;M. Peachey;P. Goebel;C. J. Eckhardt
  13. Chem. Lett. Formation of a tricyclic [2,2] paracyclophane derivative in the low-temperature photoreaction of an unsymmetric diolefin crystal Chung, C.-M.;F. Nakamura;Y. Hashimoto;M. Hasegawa
  14. Macromolecules v.22 Topochemical photoreactions of unsymmetrically substituted diolefins. 3. Photochemical behavior of 4-[2-(2-pyrazyl)ethenyl]styrene derivative crystals Hasegawa, M.;M. Aoyama;Y. Maekawa;Y. Ohashi
  15. Macromolecules v.21 Topochemical photoreactions of unsymmetrically substituted diolefins. 2. Photopolymerization of 4'-(Alkoxycarbonyl)-2,5-distyrylpyrazines Hasegawa, M.;T. Katsumata;Y. Ito;K. Saigo;Y. Iitaka
  16. Hasegawa, M.
  17. Chem. Rev. v.83 Photopolymerization of diolefin crystals Hasegawa, M.
  18. Pure Appl. Chem. v.58 Topochemical photopolymerization of diolefin crystals Hasegawa, M.
  19. Macromolecules v.24 Crystallographic interpretation of the topochemical behavior of alkyl a-cyano-4-[2-(4-pyridyl)ethenyl]cinnamates Maekawa, Y.;S. Kato;K. Saigo;M. Hasegawa;Y. Ohashi
  20. J. Am. Chem. Soc. v.107 Topochemical "Double" photo-cyclodimerization of the 1,4-dicinnamoyl-benzene crystal Hasegawa, M.;K. Saigo;T. Mori;H. Uno;M. Nohara;H. Nakanishi
  21. Bull. Chem. Soc. Jpn. v.66 Photochemical reaction of 2,3-di[(E)-styryl]pyrazine derivatives in the crystalline state and in solution Takeuchi, A.;H. Komiya;t. Mori;T. Tsutsumi;Y. Hashimoto;M. Hasegawa;Y. Iitaka;K. Saigo
  22. J. Am. Chem. Soc. v.113 Quantitative formation of a highly strained tricyclic [2,] paracyclophane derivative from a mixed crystal of ethyl and propyl α-cyano-4-[2-(4-pyridyl)ethenyl]cinnamates through a topochemical reaction Maekawa, Y.;S. Kato;M. Hasegawa
  23. a private communication Ishida, W.;Y. Takenaka(et al.)
  24. J. Chem. Soc. Topochemistry Part Ⅰ. A Survey Cohen, M. D.;G. M. J. Schmidt
  25. Pure Appl. Chem. v.27 Photodimerization in the solid state Schmidt G. M. J.
  26. Chem. Lett A novel type of polymer effect due to a rigid rod-shaped chain. Thermal depolymerization behavior of poly-2,5-distyrylpyrazine Hasegawa, M.;H. Nakanishi;T. Yurugi
  27. J. Polym. Sci., Polym. Chem. Ed. v.16 Four-center type photopolymerization in the crystalline state. Ⅸ. Characteristic features of topochemical process and polymer properties thus obtained Hasegawa, M.;H. Nakanishi;T. Yurugi
  28. Solid State Commn. v.63 Thermal depolymerization of linear polymers Hanamura, E.
  29. J. Am. Chem. Soc. v.115 Single-crystal-to-single-crystal photodimerization of cinnamic acid Enkelmann, V.;G. Wegner
  30. J. Am. Chem. Soc. v.113 Kaleidoscopic photoreaction behavior of alkyl 4-[2-(4-pyridyl)ethenyl] cinnamate crystals: A crystalline linear high polymer from the methyl ester, an "Absolute" asymmetric reaction of the ethyl ester, and two types of dimer formation from the propyl ester Chung, C.-M.;M. Hasegawa
  31. J. Am. Chem. Soc. v.113 Topochemical induction to an altermating zigzag-linear and "Syndiotactic" chain structure in the course of a [2+2]photoreaction of alkyl α-cyano-4-[2-(2-pyridyl)ethenyl] cinnamate crystals Chung, C.-M.;A. Kunita;K. Hayashi;F. Nakamura;K. Saigo;M. Hasegawa
  32. Mixed Crystals Kitaigorodsky, A. I.
  33. Acta Crystallogr. v.B35 2,5-Distyrylprazine(DSP)-1,4-bis[2-(2-pyridyl)vinyl] benzene(P2VB)(4:6); a photopolymerizable mixed crystal Nakanishi, H.;W. Jones;G. M. Parkinson
  34. Macromolecules v.24 Preparation photo-polymerization of diolefin mixed crystals Maekawa, Y.;P. J. Lim;K. Saigo;M. Hasegawa
  35. Chem. Lett. Solid-state co-crystallization of diacetylenes and its topochemical polymerization Hasegawa, M.;T. Ikeda;H. Noguchi
  36. J. Am. Chem. Soc. v.115 Photoreactive molecular complex of 2,5-distyrylpyrazine and ethyl 4-[2-(2-pyrazinyl)ethenyl]cinnamate. Formation of perfectly ordered polymer composite by crystalline-state photopolymerization Hasegawa, M.;K. Kinbara;Y. Adegawa;K. Saigo
  37. Bull. Chem. Soc. Jpn. v.66 Formation of a topochemically photoreactive mixed crystal by grinding and its mechanistic interpretation Kinbara, K.;Y. Adegawa;K. Saigo;M. Hasegawa
  38. Graduation Thesis, Faculty of Engineering, The University of Tokyo Crystalline-state photoreaction of unsymmetrically substituted diolefin compounds of β-type packing Hatada, S.
  39. Reactivity in Molecular Crystals Determining factors of molecular arrangement and reaction course in the crystalline-state photoreaction of unsymmetrically substituted diolefins Hasegawa, M.;Ohashi, Y(ed.)
  40. MS Thesis, Faculty of Engineering, The University of Tokyo Analysis of the behavior of the topochemical photoreaction Sukegawa, M.
  41. Bull. Chem. Soc. Jpn. v.68 Topochemical photopolymerization of 4-[2-(unsubstituted and methyl-substituted pyrazinyl)ethenyl]cinnamates and -thiocinnamates in the crystalline state Saigo, K.;M. Sukegawa;Y. Maekawa;M. Hasegawa
  42. Hasegawa, M.(et al.)
  43. Hasegawa, M.(et al.)