Construction of Dimensional-controlled Structures based on Conformational Chirality Control in Ring-fused Malonamides

2016 Fiscal Year Final Research Report

• Project/Area Number: 26620035
• Research Category: Grant-in-Aid for Challenging Exploratory Research
• Allocation Type: Multi-year Fund
• Research Field: Organic chemistry
• Research Institution: Tokyo University of Science
• Principal Investigator: Kawai Hidetoshi 東京理科大学, 理学部第一部化学科, 准教授 (50322798)
• Research Collaborator: FUKUSHIMA Takanori 東京工業大学, 化学生命科学研究所, 教授 (70281970) ; TADOKORO Makoto 東京理科大学, 理学部第一部化学科, 教授 (60249951) ; ONO Kosuke 東京理科大学, 理学部第一部化学科, 助教 (30579313)
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: 水素結合 / クリスタルエンジニアリング / アミド / X線構造解析 / キラル空間 / らせん / 多孔質構造 / ナノチューブ

Outline of Final Research Achievements

We have found that 2,2-indandicarboxamides assembled into the robust 2D-sheet structures based on formation of eight hydrogen bonds per molecule in the solid state. These sheet structures densely stack on one another in an interdigitated manner, therefore, any cavities, in which guests could be included, were formed among these sheets. In this work, we prepared chiral ring-fused malonamides, such as binaphthalene-fused malonamides, to create inclusion crystals with chiral inclusion cavities among these sheets by biasing the conformational chirality of the malonamide moiety toward either one, and by regulating possible hydrogen-bonding patterns. We found that the substituents at the 3,3’-position of the binaphthalene moiety effect on the conformational chirality of malonamide moiety and change the assembling dimensionality from 2D-sheet to 1D-helical structures. Furthermore, we also prepared pi-bridged bis(malonamide)s to construct hydrogen-bonded pillared-layer porous frameworks.

Free Research Field

超分子化学、有機化学