88861-53-4Relevant articles and documents
Coumarinylmethyl caging groups with redshifted absorption
Fournier, Ludovic,Aujard, Isabelle,Le Saux, Thomas,Maurin, Sylvie,Beaupierre, Sandra,Baudin, Jean-Bernard,Jullien, Ludovic
, p. 17494 - 17507 (2013)
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 470-500 nm wavelength range and a low light absorption between 350 and 400 nm. These attractive features are favorable to perform chromatic orthogonal photoactivation with UV and blue-cyan light sources, respectively. Revealing protecting groups: The coumarinylmethyl backbone was used to generate a family of photolabile protecting groups with redshifted absorption (see scheme). Several members exhibit a significant action cross section for uncaging in the 470-500 nm wavelength range and a low light absorption between 350 and 400 nm. These features are favorable for chromatic orthogonal photoactivation with UV and blue-cyan light sources, respectively.
