Control of organic chemical synthesis using vesicles: aggregates as a solvent to control regioselectivity and stereoselectivity

2021 Fiscal Year Final Research Report

• Project/Area Number: 20K15082
• Research Category: Grant-in-Aid for Early-Career Scientists
• Allocation Type: Multi-year Fund
• Review Section: Basic Section 27020:Chemical reaction and process system engineering-related
• Research Institution: Nara National College of Technology
• Principal Investigator: Hayashi Keita 奈良工業高等専門学校, 物質化学工学科, 准教授 (10710783)
• Project Period (FY): 2020-04-01 – 2022-03-31
• Keywords: 自己集合体 / 反応場 / エポキシ化

Outline of Final Research Achievements

There is a relationship between a property of vesicles and localization of embedded molecules in the vesicles. Vesicular membrane is hydrophobic, but these are a few water molecules in the vesicular membrane. The water molecular prefer to be in shallow hydrophobic region. Therefore, gradual hydrophobicity in the vesicular membrane is not uniform. The gradual hydrophobicity effects on localization of molecules. Hydrophilic molecules localize in shallow hydrophobic region. Potassium peroxymonosulfate, which is a hydrophilic oxidant, localized in shallow hydrophobic region. It was expected that potassium peroxymonosulfate epoxidized selectively a double bond neighboring at boundary surface. However, the selectively was not observed.

Free Research Field

ソフトマテリアル

Academic Significance and Societal Importance of the Research Achievements

これまでミセルやベシクルといった自己集合体は疎水性物質を封入可能であることから薬剤カプセルや有機合成における反応場としての応用が検討されてきたが，これら自己集合体の特性に着目して応用を検討した研究はあまりない．本研究では，構造依存的な特性に着目し，位置選択性を有する反応場としてベシクルの応用を検討した．その結果，位置選択性は確認されなかったが，封入した分子の局在性は制御できることが明らかとなった．この局在性の制御はミセルと比較してより安定なベシクルの構造が寄与していると考えられる．この知見をもとに，ベシクルのより幅広い応用が期待される．