AI 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.
Article Abstract
We report the clean, efficient photorelease of a series of carboxylic acids embedded in octa acid (OA) host and protected by a p-hydroxyphenacyl cage. A key role is played by the cage by providing hydrophobicity for entry into the OA enclosure and yet readily removable as a photoactivated protecting group for release from the host. The rapid photo-Favorskii rearrangement of the departing chromophore does not react with the host OA but diminishes hydrophobicity of the OA contents, leading to their facile release into the solvent.
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| http://dx.doi.org/10.1021/acs.orglett.5b00252 | DOI Listing |
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