Photorelease of incarcerated guests in aqueous solution with phenacyl esters as the trigger

Pradeepkumar Jagadesan; José P. Da Silva; Richard S. Givens; V. Ramamurthy

doi:10.1021/acs.orglett.5b00252

Photorelease of incarcerated guests in aqueous solution with phenacyl esters as the trigger

Pradeepkumar Jagadesan, José P. Da Silva, Richard S. Givens, V. Ramamurthy

Chemistry

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

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.

Original language	English (US)
Pages (from-to)	1276-1279
Number of pages	4
Journal	Organic letters
Volume	17
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.5b00252
State	Published - Mar 6 2015

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

author = "Pradeepkumar Jagadesan and {Da Silva}, {Jos{\'e} P.} and Givens, {Richard S.} and V. Ramamurthy",

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AU - Jagadesan, Pradeepkumar

AU - Da Silva, José P.

AU - Givens, Richard S.

AU - Ramamurthy, V.

PY - 2015/3/6

Y1 - 2015/3/6

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AB - 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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Photorelease of incarcerated guests in aqueous solution with phenacyl esters as the trigger

Abstract

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