Dissipative Supramolecular Reactor

2022 Fiscal Year Annual Research Report

• Project/Area Number: 21F21037
• Allocation Type: Single-year Grants
• Research Institution: Institute of Physical and Chemical Research
• Principal Investigator: 相田 卓三 国立研究開発法人理化学研究所, 創発物性科学研究センター, グループディレクター (00167769)
• Co-Investigator(Kenkyū-buntansha): GOSWAMI ABIR 国立研究開発法人理化学研究所, 創発物性科学研究センター, 外国人特別研究員
• Project Period (FY): 2021-11-18 – 2024-03-31
• Keywords: Perfluorinated Crown / Supramolecular Adhesive / Water Cluster / Membrane Transporter

Outline of Annual Research Achievements

Our novel synthetic strategy for functionalizing perfluoro crown ethers has potential applications in various fields. Strategically designed crown ether derivatives form strong supramolecular polymers in the molten state with high adhesive strength and toughness, attributed to dynamic hydrogen bonding and Fluorine-Fluorine interactions. This material shows excellent underwater and PTFE sheet adhesion, making it a potential replacement for conventional adhesive polymers. Additionally, crown ether derivatives exhibit strong interactions with water clusters, allowing them to penetrate cell membranes quickly. Whereas the corresponding nonfluorinated analog failed to penetrate the membrane bilayer even after prolonged incubation, making them suitable for medicinal chemistry and drug delivery.

Current Status of Research Progress

1: Research has progressed more than it was originally planned.

Reason

We developed an efficient method for functionalizing perfluoro crown ethers in a very short time. Initially, we struggled to functionalize the commercially available, poorly soluble Perfluoro-15-crown-5 ether, which was expected due to the strong and inert C-F bond in perfluoro carbons. However, we were pleasantly surprised to obtain a high yield of perfluorocrown ethers, allowing us to explore their potential applications in various fields of chemistry. Most importantly, we discovered that these compounds exhibit outstanding and unexpected properties, including the ability to break the hydration layer and penetrate cell membranes directly, as well as demonstrating mechanically tough supramolecular adhesion through dynamic F-F interactions.

Strategy for Future Research Activity

Perfluoro molecules are extensively used in various fields of chemistry. In near future, we would like to explore the effects of fluorine in supramolecular polymerization and medicinal chemistry. We expect to use this perfluorinated crown ether carrier to tackle the most difficult challenges of drug delivery to the brain and 19F MRI imaging.