Selected amines were allowed to form inclusion complexes with selected synthesized pillar[5]arenes. Formation of inclusion complexes were confirmed by MALDI–TOF, ESI–MS analyses and 1 H NMR spectroscopy. The complexation was supported by molecular dynamics calculations. Various pillar[5]arenes have been synthesized by BF 3 ·OE t2 (Lewis acid) catalyzed cyclization of 1,4-disubstitutedbenzenes with paraformaldehyde. Selected synthesized host macrocycles; DMpillar[5]arene ( 7 ), DPpillar[5]arene ( 8a ), DPGpillar[5]arene ( 8b ) were allowed to form inclusion complexes with N -containing guests; hexamethylenediamine ( GA ), di- n -octyl amine ( GB ) and diethyl amine ( GC ). Host–guest complex formation of the selected pillar[5]arenes with the N-containing guests has been confirmed by MALDI–TOF, ESI–MS analyses and 1 H NMR spectroscopy. ESI–MS revealed highly intense ion peaks that correspond to [pillar[5]arene@GA+Na] + for inclusion complexes of pillar[5]arenes with hexamethylenediamine ( GA ). ESI–MS confirmed formation of inclusion complexes between pillar[5]arenes with di- n -octyl amine ( GB ) and diethyl amine ( GC ) as evidenced by intense peaks that corresponds to [pillar[5]arene@GB+H] + and [pillar[5]arene@GC+H] + , respectively. Performed molecular dynamics (MD) simulations provided supportive results that indicate the formation of stable complexes between the three pillar[5]arene hosts and the guests included in this study. Hydrogen bonding and CH–π interactions were found amongst the factors that contribute significantly to the stability of these complexes.

中文翻译：

---

选定胺与柱[5]芳烃的包合物：实验和分子动力学研究

允许选定的胺与选定的合成柱[5]芳烃形成包合物。MALDI-TOF、ESI-MS 分析和 1 H NMR 光谱证实了包合物的形成。该络合得到了分子动力学计算的支持。通过BF 3 ·OE t2（路易斯酸）催化1,4-二取代苯与多聚甲醛的环化反应合成了各种柱[5]芳烃。选定的合成宿主大环；DM柱[5]芳烃(7)、DP柱[5]芳烃(8a)、DPG柱[5]芳烃(8b)与含氮客体形成包合物；六亚甲基二胺 (GA)、二正辛胺 (GB) 和二乙胺 (GC)。MALDI-TOF、ESI-MS 分析和 1 H NMR 光谱证实了所选柱[5]芳烃与含氮客体的主客体复合物形成。ESI-MS 揭示了对应于[柱[5]芳烃@GA+Na] + 柱[5]芳烃与六亚甲基二胺（ GA ）的包合物的高强度离子峰。ESI-MS 证实柱 [5] 芳烃与二正辛胺 ( GB ) 和二乙胺 ( GC ) 之间形成了包合物，这由对应于 [柱 [5] 芳烃@GB+H] + 的强峰证明和 [pillar[5]arene@GC+H] + ，分别。进行的分子动力学 (MD) 模拟提供了支持性结果，表明三柱 [5] 芳烃主体和本研究中包括的客体之间形成了稳定的复合物。在对这些复合物的稳定性有显着影响的因素中发现了氢键和 CH-π 相互作用。