Design and synthesis of 2(5H)-furanone liquid-crystal compounds based on natural molecules and biphenyl derivatives
Design and synthesis of 2(5H)-furanone liquid-crystal compounds based on natural molecules and biphenyl derivatives
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DOI：
10.1007/s11164-012-0721-8
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发表时间：
2013-04
影响因子：
3.3
通讯作者：
Shi-He Luo;Jin-Feng Xiong;Zhao‐Yang Wang;Guang-Zhen Mo
中科院分区：
文献类型：
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作者：
Shi-He Luo;Jin-Feng Xiong;Zhao‐Yang Wang;Guang-Zhen Mo
从天然分子，如薄荷醇和氨基酸出发，设计了一系列2(5H)-呋喃酮液晶化合物，并在脱水剂存在下，将n -[5-薄荷氧基-2(5H)-呋喃酮]氨基酸与联苯-4-醇或联苯-4,4 ' -二醇酯化合成。所有新化合物的结构均通过FTIR、1H NMR、质谱和元素分析得到证实。采用差示扫描量热法（DSC）、x射线衍射仪（XRD）和偏振光学显微镜（POM）对目标化合物的液晶性质进行了表征。DSC和XRD结果表明，一些含有短烷基链或氨基酸单元中苯基远离氨基酸的化合物形成了中晶相。从联苯-4,4 ' -二醇得到的产物更容易形成中形相。然而，POM没有显示光学纹理。这些研究首次为2(5H)-呋喃酮通过联苯、l-薄荷醇和氨基酸等不同功能单元的组合在液晶中的应用奠定了基础。
Starting from natural molecules, for examplel-menthol and amino acids, a series of 2(5H)-furanone liquid-crystal compounds were designed, and synthesized by esterification ofN-[5-menthoxy-2(5H)-furanonyl] amino acids with biphenyl-4-ol or biphenyl-4,4′-diol in the presence of dehydrating agents. The structures of all the novel compounds were confirmed by FTIR,1H NMR, and mass spectroscopy, and by elemental analysis. The liquid-crystal properties of the target compounds were characterized by differential scanning calorimetry (DSC), X-ray diffraction (XRD), and polarization optical microscopy (POM). The DSC and XRD results showed that some compounds containing short alkyl chains or with the phenyl far from the amino in the amino acid unit formed a mesomorphic phase. Products obtained from biphenyl-4,4′-diol were more likely to form a mesomorphic phase. However, POM revealed no optical texture. These investigations provide, for the first time, a basis for application of 2(5H)-furanones in liquid crystals by combination of different functional units, including biphenyl,l-menthol, and amino acids.