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Title: Preparation and chiroptical properties of cellulose chlorophenylcarbamate–silica hybrids having a chiral nematic mesomorphic structure
Authors: Sato, Junichi
Sugimura, Kazuki  kyouindb  KAKEN_id  orcid (unconfirmed)
Teramoto, Yoshikuni  kyouindb  KAKEN_id  orcid (unconfirmed)
Nishio, Yoshiyuki  kyouindb  KAKEN_id
Author's alias: 杉村, 和紀
寺本, 好邦
西尾, 嘉之
Keywords: Cellulose phenylcarbamate derivatives
Chiral nematic liquid crystals
Silica hybrids
Issue Date: 31-May-2019
Publisher: Elsevier BV
Journal title: Polymer
Volume: 173
Start page: 172
End page: 181
Abstract: An attempt was made to fabricate optically functional cellulosic–silica hybrid materials wherein a helically ordered mesomorphic structure of the cellulosic component was fixed. Cellulose 3-chlorophenylcarbamate (3Cl-CPC) and cellulose 4-chlorophenylcarbamate (4Cl-CPC) were synthesized by carbanilating reaction of cellulose with 3-chlorophenyl or 4-chlorophenyl isocyanate in a homogeneous solution system. The hydrophobic cellulose derivatives were examined for the solubility and liquid crystallinity in various solvents containing alkoxysilane as a main component. Concentrated (∼40 wt%) solutions of 3Cl-CPC in 3-aminopropyltrimethoxysilane (APTMS) and those of 4Cl-CPC in a mixed solvent of tetramethoxysilane (TMOS)/N, N-dimethylformamide (DMF)/dichloroacetic acid (DCA) formed a chiral nematic mesophase to impart vivid reflection colors. These liquid crystalline solutions were subjected to a sol–gel conversion process of the respective alkoxysilane components in moist air. In the process for the 4Cl-CPC lyotropic system, we utilized a "surface-coating solvent" consisting of TMOS/phenyltrimethoxysilane/DCA to facilitate the sol–gel reaction of TMOS and also to preserve the reflective coloration. Thereby a left-handed chiral nematic hybrid series of 4Cl-CPC–silica was successfully obtained as a monolithic glassy bulk showing iridescent colors. The 3Cl-CPC/APTMS lyotropics were readily converted into a colored solid form without any coating solution, resulting in production of a right-handed chiral nematic series of 3Cl-CPC–silica. Besides investigating the chiroptical characteristics of the liquid crystalline solutions and hybrids, we preliminarily tried separating a racemic compound into two enantiomers by open column chromatography using the cellulosic–silica hybrids as a filler material of the column.
Rights: © 2019. This manuscript version is made available under the CC-BY-NC-ND 4.0 license
The full-text file will be made open to the public on 31 May 2021 in accordance with publisher's 'Terms and Conditions for Self-Archiving'
This is not the published version. Please cite only the published version.
DOI(Published Version): 10.1016/j.polymer.2019.04.049
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