S_NAr has been used to synthesize various functionalized derivatives of pentafluorobenzenes which are highly specific at the para position; and consequently are ideal for building calamitic (rod-like) liquid crystalline molecular systems. Here, we display the effectiveness of S_NAr chemistry as a convenient method toward the synthesis of fluorescent liquid crystalline perfluorinated comprising ethers and thioethers in excellent yields and high purity. In the current work, we describe the synthesis, self-assembly, and mesogenic properties of new perfluorinated para-terphenyls bearing various para-substituted alkoxy and thioalkoxy chains. The terphenyl core was prepared using Cu(I) (or Cu(I)/phenanthroline)-catalyzed decarboxylative carbon–carbon (or carbon–oxygen [sulfur]) cross-coupling from the analogous aromatic iodide and fluorobenzoate potassium salt. The molecular structures of the prepared perfluorinated terphenyls were demonstrated with ¹H, ¹³C, and ¹⁹F NMR, as well as FT-IR and X-ray crystallography. The liquid crystalline properties and mesogenic phases were characterized with differential scanning calorimetry and high-resolution polarized optical microscope. Both UV–visible absorbance and emission spectra demonstrated solvatochromism. Supramolecular self-assembly of the generated perfluorinated para-terphenyls was monitored by van der Waals and π–π stacking interaction forces. The creation of nanofibrous architectures was monitored by scanning electron microscopy.

中文翻译：

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荧光含氟液晶的合成、表征和自组装

S _N Ar 已被用于合成五氟苯的各种功能化衍生物，这些衍生物在对位具有高度特异性；因此是构建棒状（棒状）液晶分子系统的理想选择。在这里，我们展示了 S _N Ar 化学作为合成荧光液晶全氟化物的便捷方法的有效性，该方法包括醚和硫醚，产率高，纯度高。在目前的工作中，我们描述了带有各种对位的新型全氟对三联苯的合成、自组装和介晶性质。-取代的烷氧基和硫代烷氧基链。三联苯核是使用Cu（I）（或Cu（I）/菲咯啉）催化的碳-碳（或碳-氧[硫]）交叉偶联从类似的芳香碘化物和氟苯甲酸钾盐制备的。制备的全氟三联苯的分子结构通过¹ H、¹³ C 和¹⁹ F NMR 以及 FT-IR 和 X 射线晶体学证明。液晶性质和介晶相用差示扫描量热法和高分辨率偏光显微镜表征。紫外-可见吸收光谱和发射光谱都证明了溶剂化变色。生成的全氟化对位的超分子自组装三联苯通过范德华力和π-π堆积相互作用力进行监测。通过扫描电子显微镜监测纳米纤维结构的产生。