Scholarlink

<p>Water-soluble macrocycles are useful molecular hosts for drug delivery, stimuli-responsive materials, water purification and many other applications. However, controlling the host-guest chemistry of macrocycles such as cyclodextrins under physiologically relevant conditions is a major challenge. Here we demonstrate the use of dynamic pericyclic chemistry to derivatise guests for cyclodextrins under mild conditions, thereby turning off molecular recognition. We show that the Diels-Alder [4 + 2] cycloaddition reaction between anthracene derivatives and activated alkenes proceed rapidly, selectively and reversibly in water under ambient conditions. This reaction can be used to modulate binding of both native and modified β-cyclodextrins to the anthracene. By appropriate choice of conditions, the resulting chemical reaction network could also operate under non-equilibrium steady state conditions. Finally, alkene scavengers could induce the retro-Diels Alder reactions, allowing the use of the pericyclic reaction system as a molecular switch.</p><p></p>

错误：搜索内容不能为空，请输入英文关键词
错误：关键词超出字数限制，请精简
高级检索

Controlling cyclodextrin host-guest complexation in water with dynamic pericyclic chemistry

  • 期刊论文

  • 出版模式：

    开放获取

  • 发表日期：

    2025年12月26日

查看全文
  • Marius Gaedke,
  • Anja Ramström,
  • Daisy R. S. Pooler,
  • Fredrik Schaufelberger

摘要

Water-soluble macrocycles are useful molecular hosts for drug delivery, stimuli-responsive materials, water purification and many other applications. However, controlling the host-guest chemistry of macrocycles such as cyclodextrins under physiologically relevant conditions is a major challenge. Here we demonstrate the use of dynamic pericyclic chemistry to derivatise guests for cyclodextrins under mild conditions, thereby turning off molecular recognition. We show that the Diels-Alder [4 + 2] cycloaddition reaction between anthracene derivatives and activated alkenes proceed rapidly, selectively and reversibly in water under ambient conditions. This reaction can be used to modulate binding of both native and modified β-cyclodextrins to the anthracene. By appropriate choice of conditions, the resulting chemical reaction network could also operate under non-equilibrium steady state conditions. Finally, alkene scavengers could induce the retro-Diels Alder reactions, allowing the use of the pericyclic reaction system as a molecular switch.