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Volumn 118, Issue 40, 1996, Pages 9498-9508

Photopolymerization of carbohydrate-based discotic mesogens. Synthesis and phase properties of 1,2,3,4,6-penta-O-(trans-3,4-dialkoxycinnamoyl)-(D)-glucopyranoses and their oligomers

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CARBOHYDRATE ANALYSIS; DRUG SYNTHESIS; PHOTOCHEMISTRY; POLYMERIZATION; X RAY ANALYSIS;

EID: 0029956352     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961665x     Document Type: Article
Times cited : (21)

References (62)
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    • For details on cinnamate photochemistry in anisotropic phases, see: (a) Schmidt, G. M. J., et al. Solid Slate Photochemistry; Ginsburg, D., Ed.; Verlag-Chemie: Weinheim, 1976. (b) Venkatesan, K.; Ramamurthy, V. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: Weinheim, 1991; pp 133-184. (c) Weiss, R. G. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: Weinheim, 1991; pp 603-690. (d) Enkelman, V.; Wegner, G.; Novak, K.; Wagener, K. B. J. Am. Chem. Soc. 1993, 115, 203. (e) Greiving, H.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Desvergne, J. P.; Bouas-Laurent, H. J. Chem. Soc., Chem. Commun. 1994, 1075.
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    • Venkatesan, K.1    Ramamurthy, V.2
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    • Ramamurthy, V., Ed.; VCH: Weinheim
    • For details on cinnamate photochemistry in anisotropic phases, see: (a) Schmidt, G. M. J., et al. Solid Slate Photochemistry; Ginsburg, D., Ed.; Verlag-Chemie: Weinheim, 1976. (b) Venkatesan, K.; Ramamurthy, V. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: Weinheim, 1991; pp 133-184. (c) Weiss, R. G. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: Weinheim, 1991; pp 603-690. (d) Enkelman, V.; Wegner, G.; Novak, K.; Wagener, K. B. J. Am. Chem. Soc. 1993, 115, 203. (e) Greiving, H.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Desvergne, J. P.; Bouas-Laurent, H. J. Chem. Soc., Chem. Commun. 1994, 1075.
    • (1991) Photochemistry in Organized and Constrained Media , pp. 603-690
    • Weiss, R.G.1
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    • For details on cinnamate photochemistry in anisotropic phases, see: (a) Schmidt, G. M. J., et al. Solid Slate Photochemistry; Ginsburg, D., Ed.; Verlag-Chemie: Weinheim, 1976. (b) Venkatesan, K.; Ramamurthy, V. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: Weinheim, 1991; pp 133-184. (c) Weiss, R. G. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: Weinheim, 1991; pp 603-690. (d) Enkelman, V.; Wegner, G.; Novak, K.; Wagener, K. B. J. Am. Chem. Soc. 1993, 115, 203. (e) Greiving, H.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Desvergne, J. P.; Bouas-Laurent, H. J. Chem. Soc., Chem. Commun. 1994, 1075.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 203
    • Enkelman, V.1    Wegner, G.2    Novak, K.3    Wagener, K.B.4
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    • For details on cinnamate photochemistry in anisotropic phases, see: (a) Schmidt, G. M. J., et al. Solid Slate Photochemistry; Ginsburg, D., Ed.; Verlag-Chemie: Weinheim, 1976. (b) Venkatesan, K.; Ramamurthy, V. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: Weinheim, 1991; pp 133-184. (c) Weiss, R. G. In Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH: Weinheim, 1991; pp 603-690. (d) Enkelman, V.; Wegner, G.; Novak, K.; Wagener, K. B. J. Am. Chem. Soc. 1993, 115, 203. (e) Greiving, H.; Hopf, H.; Jones, P. G.; Bubenitschek, P.; Desvergne, J. P.; Bouas-Laurent, H. J. Chem. Soc., Chem. Commun. 1994, 1075.
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    • Greiving, H.1    Hopf, H.2    Jones, P.G.3    Bubenitschek, P.4    Desvergne, J.P.5    Bouas-Laurent, H.6
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    • note
    • Diffraction patterns of the higher temperature crystalline phases were not recorded due to our inability to thermostat the samples with adequate precision.
  • 56
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    • note
    • -1.
  • 58
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    • note
    • The 7αGP and 7βGP exhibit photochemical behavior that is similar to their tetradecyl homologues. Irradiations of mesophases near the clearing temperatures or of solid II phases at 25-35 °C gave high photoconversions with no detectable changes in optical textures. Proton NMR and IR spectra of the photoproducts were comparable to those of similarly irradiated tetradecyl homologues. However, GPC analyses of oligomers from irradiation of the various phases of the 7GP led only to very small peaks from which no usable information could be extracted. The oligomers were not completely soluble in the initial eluent, THF, and do not have sufficiently different indices of refraction from a second eluent, toluene, to allow reasonable signals from the RI detector. For that reason, we have emphasized data from the longer homologues.
  • 59
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    • note
    • w values for unirradiated 14βGP, the degrees of oligomerization have been calculated assuming the monomeric molecular masses from the appropriate data set (rather than using 2950, the correct molar mass).
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    • Nakanishi, K.1    Berova, N.2


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