Coumarinylmethyl caging groups with redshifted absorption.
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.
Ecole Normale Supérieure, Département de Chimie, UMR CNRS-ENS-UPMC, Paris 06 8640 PASTEUR, 24, rue Lhomond, 75231 Paris Cedex 05 (France).
Ludovic
L
Fournier
Isabelle
I
Aujard
Thomas
T
Le Saux
Sylvie
S
Maurin
Sandra
S
Beaupierre
Jean-Bernard
JB
Baudin
Ludovic
L
Jullien
D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry*; D008027:Light; D010782:Photolysis; D013053:Spectrophotometry; D014466:Ultraviolet Rays
D003374:Coumarins
UV/Vis spectroscopy; caged compounds; photochemistry; photolysis; protecting groups