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Thermotropic Liquid Crystalline Behaviors of 4-{4'-(nitrophenylazo)phenoxy}alkanoic Acids and 4-{4'-(nitrophenylazo)phenoxy}alkanoyl Chlorides  

Jeong, Seung Yong (Department of Polymer Science and Engineering, Dankook University)
Ma, Yung Dae (Department of Polymer Science and Engineering, Dankook University)
Publication Information
Applied Chemistry for Engineering / v.19, no.5, 2008 , pp. 504-511 More about this Journal
Abstract
Two kinds of nitroazobenzene derivatives: 4-{4'-(nitrophenylazo)phenoxy}alkanoic acids (NAAn, n = 2~8, 10, number of methylene units in the alkyl chain) and 4-{4'-(nitrophenylazo)phenoxy}alkanoyl chlorides (NACn, n = 2~8, 10) were synthesized, and their thermotropic liquid crystalline behaviors were investigated. NAA6 formed an enantiotropic nematic phase, while the remainders, except NAA2, showed monotropic nematic phases. Isotropic-nematic transition temperature ($T_{iN}$) and change of entropy (${\Delta}S$) at $T_{iN}$ for both of NAAn and NACn varied by the change of n, and pronounced odd-even effects of n were also observed. However, the $T_{iN}$ and ${\Delta}S$ values of NAAn were much higher than those of NACn. This fact may be attributed to the hydrogen bonding between carboxyl groups. Thermal properties and degree of order in the mesophase and the magnitude of the odd-even effects of both NAAn and NACn were significantly different from those reported for 4-(alkoxy)-4'-nitroazobenzenes. It was discussed in terms of the differences in the molecular anisotropy and the temperature-dependent flexibility of the substituted groups.
Keywords
nitroazobenzene; nematic phase; odd-even effect; the number of methylene units; substituent effect;
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