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Thermotropic Liquid Crystalline Behavior of Penta-O-4-{4'-(cyanophenylazo)phenoxy}alkyl-D-glucopyranoses  

Jeong, Seung Yong (Center for Photofuctional Energy Materials, Dankook University)
Kim, In Soo (Center for Photofuctional Energy Materials, Dankook University)
Ma, Yung Dae (Center for Photofuctional Energy Materials, Dankook University)
Publication Information
Applied Chemistry for Engineering / v.20, no.6, 2009 , pp. 603-611 More about this Journal
Abstract
Thermotropic liquid crystalline behavior of a homologous series of penta-O-4-{4'-(cyanophenylazo)phenoxy}alkyl-D-glucopyranoses(CAGETn, n = 2~10, the number of methylene units in the spacer) has been investigated. The CAGETn with n of 2 and 7 exhibited enantiotropic nematic phases whereas other derivatives showed monotropic nematic phases. This is the first report of glucose derivatives that form thermotropic nematic phases. The isotropic-nematic transition temperatures ($T_{iNS}$) of CAGETns and their entropy variation at $T_{iN}$ showed the odd-even effect as a function of n. This behavior was rationalized in terms of the change in the average shape of the side chains as the parity of the spacer is varied. This rationalization also accounts for the observed variation of nematic-crystalline phase transition temperatures ($T_{NkS}$) and associoated entropy change at $T_{Nk}$. The entropy change at $T_{iN}$ or $T_{Nk}$ reaches a mininum at n = 3, before it increases again for n = 4. This may be attributed to the difference in the arrangement of the side groups. The mesophase properties of CAGETns were entirely different from those reported for partially or fully alkylated glucopyranoses. This result suggests that the degree of substitution and chemical structure of the substituents play an important role in the formation of the mesophase structures in the liquid crystals.
Keywords
glucose; cyanoazobenzene; spacer length; nematic phase;
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