Functional self-assembled materials of interlocked molecules through solvophobic effects and dispersive forces

2021 Fiscal Year Final Research Report

• Project/Area Number: 19K05591
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Review Section: Basic Section 35010:Polymer chemistry-related
• Research Institution: Tokushima Bunri University
• Principal Investigator: TOMINAGA Masahide 徳島文理大学, 薬学部, 准教授 (60361507)
• Project Period (FY): 2019-04-01 – 2022-03-31
• Keywords: インターロック化合物 / カテナン / 環状化合物 / 球状微粒子 / 分子集合体 / 包接結晶 / 溶媒効果 / 分散力

Outline of Final Research Achievements

Macrocycles and their [2]catenanes were synthesized by the one-step reactions of disubstituted adamantanes bearing halophenol units and 3,6-dichlorotetrazine in moderate yields by utilizing solvophobic effects and dispersion forces originated in the aliphatic and bulky natures of the adamantane units. Further, these compounds were organized into spherical particles and their fused network aggregates, whose formations were similarly attributed to solvophobic effects. The crystalline materials containing volatile organic compounds and carcinogenic substances were constructed from crystallization of catenanes. Macrocycles were assembled into tubular and columnar structures containing 1D channels in the crystalline states, which exhibited permanent intrinsic porosity due to mainly dispersion forces between the adamantane units, and adsorption of various guest molecules in a single-crystal to single-crystal fashion. Among them, the pseudorotaxane structures were produced.

Free Research Field

有機化学

Academic Significance and Societal Importance of the Research Achievements

独自に見出したアダマンタン誘導体の疎溶媒効果・分散力を活用して、カテナンなどのインターロック化合物の合成と、これを基盤とした球状微粒子の構築、揮発性有機化合物を包接可能な結晶性材料の開発の機能創出に取り組んでいる研究例は限られている。単一分子システムの動的挙動や分子認識能を、ナノからバルクスケールの複数分子システムへと適用することにより、化粧品、センサー、塗料、フィルムなどのマテリアルサイエンスの分野へと幅広く応用できる可能性がある。得られた成果は自己組織化化学や超分子化学などのナノサイエンスの分野、特にナノ微粒子や多孔質材料の研究領域に多様な知見と有意な波及効果をもたらすと考えられる。