Kikuchi Yuji, Ono Kosuke, Johmoto Kohei, Uekusa Hidehiro, Iwasawa Nobuharu
Department of Chemistry, Tokyo Institute of Technology and JST-CREST, 2-12-1, O-okayama, Meguro-ku, Tokyo 152-8551 (Japan).
Chemistry. 2014 Nov 24;20(48):15737-41. doi: 10.1002/chem.201405163. Epub 2014 Oct 21.
The inclusion of two different guest molecules in a macrocyclic boronic ester in organic solvent utilizing only π-stacking interactions has been successfully realized. For this purpose, a new tetrol which has an appropriate distance between two 1,2-diol units for the inclusion of two aromatic molecules is designed and synthesized. Simple mixing of the new tetrol with 2,7-pyrenediboronic acid in the presence of pyrene-4,5-quinone efficiently affords the desired macrocyclic boronic ester, which is found by (1)H NMR spectroscopy, ESI-MS, and isothermal titration calorimetry studies to include one molecule each of a dinitronaphthalimide derivative and pyrene. Furthermore, inclusion of two planar molecules within the macrocyclic boronic ester is revealed by X-ray analysis.
仅利用π-堆积相互作用，在有机溶剂中成功实现了在大环硼酸酯中包含两种不同客体分子。为此，设计并合成了一种新的四醇，其两个1,2-二醇单元之间具有合适的距离以容纳两个芳香分子。在芘-4,5-醌存在下，将新的四醇与2,7-芘二硼酸简单混合，有效地得到了所需的大环硼酸酯，通过¹H NMR光谱、ESI-MS和等温滴定量热法研究发现，该大环硼酸酯包含一个二硝基萘二甲酰亚胺衍生物分子和一个芘分子。此外，X射线分析表明大环硼酸酯中包含两个平面分子。
