Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 19, Issue 51, Pages 17494-17507Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201302630
Keywords
caged compounds; photochemistry; photolysis; protecting groups; UV; Vis spectroscopy
Categories
Funding
- ANR (Proteophane) [PCV 2008]
- Ministere de la Recherche
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The small and synthetically easily accessible coumarinylmethyl backbone has been modified to generate a family of photolabile protecting groups with redshifted absorption. We relied on introducing electron-donating groups in the 7 position and electron-withdrawing groups in the 2-, and 2- and 3 positions. In particular, we showed that the diethylamino-thiocoumarylmethyl and the diethylamino-coumarylidenemalononitrilemethyl are relevant for uncaging with cyan light. They both exhibit a significant action cross section for uncaging in the 470-500nm wavelength range and a low light absorption between 350 and 400nm. These attractive features are favorable to perform chromatic orthogonal photoactivation with UV and blue-cyan light sources, respectively.
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