Helical arrangement of a hydrogen-bonded columnar liquid crystal induced by a centered triphenylene derivative bearing chiral side-chains

Shinsuke Ishihara, Yusuke Furuki, Shinji Takeoka

    Research output: Contribution to journalArticle

    10 Citations (Scopus)

    Abstract

    A hydrogen-bonded helical columnar liquid crystal was synthesized, in which the helical structure is induced by a centered triphenylene derivative bearing chiral side-chains. The triphenylene derivative, 2,6,10-tris(carboxymethoxy)-3,7,11-tris((S)-(-)-2-methyl-1-butanoxy) triphenylene (TPC4(S)), and a dendric amphiphile, 3,5-bis-(3,4-bis-dodecyloxy-benzyloxy)-N-pyridine-4-yl-benzamide (DenC12), were mixed in a 1:3 ratio to obtain a complex, TPC4(S)-DenC12. Analyses by 1H-NMR spectroscopy, diffusion ordered spectroscopy (DOSY), CD spectroscopy, infrared (IR) spectroscopy, polarized optical microscopy (POM), differential scanning calorimetry (DSC), and X-ray diffractometry revealed that TPC-4(S)-DenC12 self-assembles to form helical columnar stacks in solution and a helical columnar liquid crystal in bulk. The hydrogen bonding between TPC4(S) and DenC12 is essential for the helical columnar organization, and the preference for a one-handed helical conformation is likely derived from the steric interaction between the chiral side-chains and the dendric amphiphiles in the packing of the hydrogen-bonded columnar assemblies.

    Original languageEnglish
    Pages (from-to)1097-1104
    Number of pages8
    JournalPolymers for Advanced Technologies
    Volume19
    Issue number8
    DOIs
    Publication statusPublished - 2008 Aug

    Fingerprint

    Bearings (structural)
    Liquid Crystals
    Amphiphiles
    Liquid crystals
    Hydrogen
    Spectroscopy
    Derivatives
    Pyridine
    X ray diffraction analysis
    Nuclear magnetic resonance spectroscopy
    Optical microscopy
    Conformations
    Differential scanning calorimetry
    Infrared spectroscopy
    Hydrogen bonds
    triphenylene

    Keywords

    • Columnar structure
    • Hydrogen bonding
    • Induced helicity
    • Liquid crystal
    • Supramolecular chemistry

    ASJC Scopus subject areas

    • Polymers and Plastics

    Cite this

    Helical arrangement of a hydrogen-bonded columnar liquid crystal induced by a centered triphenylene derivative bearing chiral side-chains. / Ishihara, Shinsuke; Furuki, Yusuke; Takeoka, Shinji.

    In: Polymers for Advanced Technologies, Vol. 19, No. 8, 08.2008, p. 1097-1104.

    Research output: Contribution to journalArticle

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