In this article, we report on the synthesis and characterization of crown-ether appended hexaazatrinaphthylene derivatives with two alkoxy chains. The complexation of a derivative having shorter alkoxy chains with metal ions, such as NaI and KI, prompts remarkable changes in the electronic properties of sold states, because of changing intermolecular interactions. Polarized optical microscopic observation, X-ray diffraction pattern measurement and differential scanning calorimetry reveal that a compound with longer alkoxy chains self-assembles into the formation of the columnar liquid-crystalline phase. Moreover, the addition of benzenesulphonic acid influences the self-assembled liquid-crystalline structures, as well as the electronic properties. The complexation of the derivative having longer alkoxy chains with benzenesulphonic acid induces a larger dipole moment, compared to that before complexation, thereby leading to the enhancement of intermolecular interaction, such as dipole-dipole interaction. Also, peaks in UV-vis absorption and fluorescent spectra show a dramatically bathochromic shift, due to their intermolecular interaction, such as the π-π interaction.

中文翻译：

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冠醚基六氮杂萘并萘基液态结晶衍生物的合成与表征

在本文中，我们报告了带有两个烷氧基链的冠醚附加六氮杂萘并萘衍生物的合成和表征。具有较短烷氧基链的衍生物与金属离子（例如NaI和KI）的络合，由于分子间相互作用的变化，会促使销售态电子性质发生显着变化。偏光显微镜观察，X射线衍射图测量和差示扫描量热法显示，具有较长烷氧基链的化合物自组装成柱状液晶相。而且，苯磺酸的加入影响自组装的液晶结构以及电子性能。与络合前相比，具有更长的烷氧基链的衍生物与苯磺酸的络合引起更大的偶极矩，从而导致分子间相互作用如偶极-偶极相互作用的增强。而且，由于它们的分子间相互作用，例如π-π相互作用，UV-vis吸收和荧光光谱的峰显示出显着的红移。