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

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

Chemistry

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

16 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

Organic Chemistry
Physical and Theoretical Chemistry
Biochemistry

Access to Document

10.1021/acs.orglett.5b00252

Fingerprint Dive into the research topics of 'Photorelease of incarcerated guests in aqueous solution with phenacyl esters as the trigger'. Together they form a unique fingerprint.

Cite this

@article{4fc450b7659d4d2bb95ba6d078343399,

title = "Photorelease of incarcerated guests in aqueous solution with phenacyl esters as the trigger",

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 Vaidhyanathan Ramamurthy",

year = "2015",

month = mar,

day = "6",

doi = "10.1021/acs.orglett.5b00252",

language = "English (US)",

volume = "17",

pages = "1276--1279",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "5",

}

TY - JOUR

T1 - Photorelease of incarcerated guests in aqueous solution with phenacyl esters as the trigger

AU - Jagadesan, Pradeepkumar

AU - Da Silva, José P.

AU - Givens, Richard S.

AU - Ramamurthy, Vaidhyanathan

PY - 2015/3/6

Y1 - 2015/3/6

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=84929170207&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84929170207&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.5b00252

DO - 10.1021/acs.orglett.5b00252

M3 - Article

C2 - 25705813

AN - SCOPUS:84929170207

VL - 17

SP - 1276

EP - 1279

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 5

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Cite this