Isotope Effects in Photochemistry:  Application to Chromatic Orthogonality

The main challenge in developing new wavelength-specific photolabile protecting groups is the rigorous control of the photolysis rate. This rate is controlled by two factors:  the chromophore absorbance and the reaction quantum yield. Fine-tuning the properties by changing substituents or structural...

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Bibliographic Details
Published inOrganic letters Vol. 9; no. 14; pp. 2649 - 2651
Main Authors Blanc, Aurélien, Bochet, Christian G
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.07.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ETHERS
2-NITROBENZYL COMPOUNDS
REACTION-MECHANISMS
PROTECTING GROUPS
RELEASE
CLEAVAGE
DERIVATIVES
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Summary:The main challenge in developing new wavelength-specific photolabile protecting groups is the rigorous control of the photolysis rate. This rate is controlled by two factors:  the chromophore absorbance and the reaction quantum yield. Fine-tuning the properties by changing substituents or structural features is difficult, because both factors are independently affected. By the use of the kinetic isotope effect, we could tune the quantum yield without altering the absorbance, and hence control the overall reaction rate. We exemplified this approach with chromatically orthogonally protected diesters.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol070820h