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Synthesis and characterization of photoactive columnar liquid crystals containing azobenzene and quinoxaline moieties
Journal of Molecular Liquids ( IF 5.3 ) Pub Date : 2020-03-21 , DOI: 10.1016/j.molliq.2020.112944
Welisson P. Silva , Edivandro Girotto , Hugo Gallardo , Rodrigo Cristiano

In this study, we report the synthesis and characterization of thermal and optical properties of photoactive molecules containing both quinoxaline and azobenzene moieties. Two series of molecules in which the quinoxaline is connected to the azobenzene without a flexible alkyl chain were accessed via esterification reactions between the 4-(hydroxy)-4′-substituted-azobenzenes (substituents on azobenzene ring: -ODecyl, -NO2, -Cl, -OMe and -O(2-Et-Hexyl)) and 2,3-bis(4-methoxyphenyl)quinoxaline-6-carboxylic acid or 2,3-bis(3,4-bis(dodecyloxy)phenyl)quinoxaline-6-carboxylic acid. The other two series of molecules containing an alkyl chain spacer of six carbon atoms between both aromatic systems were obtained via O-alkylation reactions of the same quinoxaline acids mentioned above with 4-(6-bromohexyloxy)-4′-substituted-azobenzenes. The absence of long alkyl chains on the quinoxaline side led to glassy materials and some of them showed a calamitic type mesophase, mostly monotropic. On the other hand, a considerable increase of side-chain density in compounds containing the long alkyl chains on the quinoxaline ring gave materials with hexagonal columnar phases (Colh). In these materials, the incorporation of small polar substituents such as nitro or chlorine on the azobenzene system increased the stability of the Colh. The presence of alkyl chain spacer was responsible for lowering the melting points and room temperature Colh phases were observed for some of these compounds. The molecular arrangement of molecules on the Colh is different from the analogous without the alkyl spacer between the aromatic systems. The absorption and fluorescence properties, as well as the photoisomerization of the azo group in solution were investigated. Colh phase was able to be destroyed under UV light and this process was found to be reversible.



中文翻译:

含偶氮苯和喹喔啉部分的光敏柱状液晶的合成与表征

在这项研究中,我们报告了同时包含喹喔啉和偶氮苯部分的光敏分子的热学性质和光学性质的合成和表征。通过4-(羟基)-4'-取代的偶氮苯(偶氮苯环上的取代基:-ODecyl,-NO 2, -Cl,-OMe和-O(2-Et-己基))和2,3-双(4-甲氧基苯基)喹喔啉-6-羧酸或2,3-双(3,4-双(十二烷氧基)苯基)喹喔啉-6-羧酸。通过O获得了在两个芳族系统之间含有六个碳原子的烷基间隔基的另外两个分子上述相同的喹喔啉酸与4-(6-溴己氧基)-4'-取代的偶氮苯的-烷基化反应。喹喔啉侧缺少长烷基链会导致产生玻璃状物质,其中一些表现出cal型中间相,大部分为单相性。另一方面,在喹喔啉环上含有长烷基链的化合物中,侧链密度的显着增加使材料具有六方柱状相(Col h)。在这些材料中,在偶氮苯系统上引入小的极性取代基(例如硝基或氯)可提高Col h的稳定性。烷基链间隔物的存在是负责降低熔点和室温山口ħ这些化合物中的某些观察到了相。Col h上分子的分子排列不同于在芳族系统之间没有烷基间隔基的类似物。研究了溶液中偶氮基的吸收和荧光性质以及光致异构化。Col h相能够在紫外线下被破坏,并且发现该过程是可逆的。

更新日期:2020-03-22
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