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Synthesis and liquid crystalline properties of novel fluorinated N-benzoyl thiourea compounds. Effect of perfluoroalkyl chains on the thermal behavior and smectic phases stability
Journal of Fluorine Chemistry ( IF 1.9 ) Pub Date : 2017-10-26 , DOI: 10.1016/j.jfluchem.2017.10.008
Monica Iliş , Marin Micutz , Iuliana Pasuk , Teodora Staicu , Viorel Cîrcu

A series of novel N-benzoyl-N’-aryl thiourea derivatives (BTU) bearing different number of alkoxy groups in terminal positions of benzoyl unit and a perfluorooctyl group on the other side have been designed and prepared. Their liquid crystalline properties were investigated by a combination of three techniques: polarizing optical microscopy (POM), differential scanning calorimetry (DSC) and variable-temperature powder X-ray diffraction (XRD). Their thermal stability was studied by thermogravimetric analysis (TG). It was found that only the compounds which have only one alkoxy chain attached to benzoyl unit, 1a and 1b, show calamitic mesomorphic behavior, with smectic A and C phases being displayed. The type and stability of these mesophases are greatly influenced by the alkyl chain length as well as by the presence of perfluorooctyl group. The clearing and the mesophase ranges are significantly increased with the incorporation of perfluoroalkyl chains when compared to non-fluorinated analogues, with almost 40 °C. The attachment of additional alkoxy groups on the benzoyl moiety led to a significant decrease of the clearing points and suppression of the mesogenic character.



中文翻译:

新型氟化N-苯甲酰基硫脲化合物的合成和液晶性能。全氟烷基链对热行为和近晶相稳定性的影响

设计并制备了一系列新颖的N-苯甲酰基-N'-芳基硫脲衍生物(BTU),其在苯甲酰基单元的末端位置和另一侧的全氟辛基具有不同数目的烷氧基。通过三种技术的组合研究了它们的液晶特性:偏振光学显微镜(POM),差示扫描量热法(DSC)和变温粉末X射线衍射(XRD)。通过热重分析(TG)研究了它们的热稳定性。发现仅具有仅一个烷氧基链连接至苯甲酰基单元1a1b的化合物,显示出弯曲的介晶行为,并显示出近晶的A和C相。这些中间相的类型和稳定性受烷基链长以及全氟辛基基团的存在的影响。当与全氟烷基类似物相比,全氟烷基链的引入,其澄清和中间相的范围显着增加,几乎达到40°C。在苯甲酰基部分上附加的烷氧基的附着导致清除点的显着降低和介晶特性的抑制。

更新日期:2017-10-26
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