Abstract Although there are several merits to use organic ionic salts as functional materials, crystal structures of these salts have not been systematically investigated. We synthesized a series of styrylpyridinium and styrylquinolinium with iodide, p-toluenesulfonate, 1-pyrenesulfonate or tetraphenylborate, and their single crystals for X-ray crystallographic analysis were grown. Consequently, 11 crystal structures, based on three iodides, one p-toluenesulfonate, three 1-pyrenesulfonates and one tetraphenylborate, including solvated ones and polymorphs were analyzed. Cation stacking structures were able to be classified into three types, and two structures without cation stacking were also found. Although the HOMO levels of the anions were found to be higher than the LUMO levels of the cations by the DFT calculation, apparent evidence on the electron transfer was not detected. One of the plausible reasons is lack of face-to-face overlapping between cations and anions in the crystal structures.

中文翻译：

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一些π共轭离子晶体对电子应用的晶体结构表征

摘要 尽管使用有机离子盐作为功能材料有几个优点，但尚未系统地研究这些盐的晶体结构。我们用碘化物、对甲苯磺酸盐、1-芘磺酸盐或四苯基硼酸盐合成了一系列苯乙烯基吡啶鎓和苯乙烯基喹啉鎓，并生长了它们用于 X 射线晶体学分析的单晶。因此，分析了基于三种碘化物、一种对甲苯磺酸盐、三种 1-芘磺酸盐和一种四苯基硼酸盐的 11 种晶体结构，包括溶剂化物和多晶型物。阳离子堆积结构可以分为三种类型，还发现了两种没有阳离子堆积的结构。尽管通过 DFT 计算发现阴离子的 HOMO 能级高于阳离子的 LUMO 能级，没有检测到电子转移的明显证据。合理的原因之一是晶体结构中阳离子和阴离子之间缺乏面对面的重叠。