AI Article Synopsis

  • The study investigates how light can be used to break down carboxylic acid esters linked to a chromophore, allowing the release of acids into water from a capsule made of octaacid molecules.
  • The chromophore remains trapped in the octaacid either as a simple alcohol or bonded through a process involving hydrogen abstraction.
  • This method not only controls the release of hydrophobic acids with light but also provides insights into the behavior of intermediates that show both radical and ionic properties during the photolysis process.

Article Abstract

Photolysis of aqueous solutions of carboxylic acid esters of 7-(methoxycoumaryl)-4-methanol included within the capsule made up of two molecules of octaacid released the acids in water. The trigger 7-(methoxycoumaryl)-4-methyl chromophore remains within octaacid either as the alcohol or as an adduct with the host octaacid through a hydrogen abstraction process. The method established here offers a procedure to release hydrophobic acid molecules in water at will in a timely manner with light. In addition, the system offers an unanticipated opportunity to probe the mechanistic dichotomy of a diradicaloid intermediate expressing both radical and ionic behavior when generated by coumarylmethyl ester photolysis in a hydrophobic environment.

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http://dx.doi.org/10.1021/acs.orglett.6b02655DOI Listing

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Article Synopsis
  • The study investigates how light can be used to break down carboxylic acid esters linked to a chromophore, allowing the release of acids into water from a capsule made of octaacid molecules.
  • The chromophore remains trapped in the octaacid either as a simple alcohol or bonded through a process involving hydrogen abstraction.
  • This method not only controls the release of hydrophobic acids with light but also provides insights into the behavior of intermediates that show both radical and ionic properties during the photolysis process.
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Article Synopsis
  • The study demonstrates the effective photorelease of carboxylic acids using a system where these acids are enclosed in octa acid (OA) and protected by a light-sensitive p-hydroxyphenacyl cage.
  • The protective cage offers hydrophobic qualities that allow the acids to enter the OA but can be easily removed upon exposure to light.
  • Once the cage is removed, the resulting structural change decreases the hydrophobic nature of the contents, facilitating the release of the acids into the surrounding solvent.
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