Journal
POLYMER CHEMISTRY
Volume 7, Issue 29, Pages 4793-4801Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6py00967k
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Funding
- Japan Society for the Promotion of Science (JSPS) KAKENHI [26410129]
- Grants-in-Aid for Scientific Research [26410129] Funding Source: KAKEN
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Chiral fluorescent sensors were designed and synthesized from naturally occurring optically active cellulose, in which a terthienyl moiety was used as a fluorescent signaling unit, and their chiral recognition abilities were investigated on the basis of an enantioselective fluorescence response to aromatic nitro compounds as quenchers. A cellulose phenylcarbamate derivative (Ce-1b) exhibited an apparent enantioselectivity for various types of aromatic nitro compounds containing either central or axial chirality. Considering the fact that a corresponding monosaccharide derivative showed almost no enantioselectivity, the chiral recognition ability of the cellulose-based fluorescence sensor is attributed to its regular highero-rder structures, probably a one-handed helical conformation. The resolution ability of Ce-1b as a chiral stationary phase for high-performance liquid chromatography was basically higher than that of the previously reported cellulose tris(phenylcarbamate), revealing that the terthienyl-based pendant provides attractive chiral recognition sites along the helical backbone as well as the fluorescent functionality.
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