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Coumarinylmethyl Caging Groups with Redshifted Absorption
Author(s) -
Fournier Ludovic,
Aujard Isabelle,
Le Saux Thomas,
Maurin Sylvie,
Beaupierre Sandra,
Baudin JeanBernard,
Jullien Ludovic
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302630
Subject(s) - cyan , absorption (acoustics) , photochemistry , redshift , wavelength , chemistry , materials science , optoelectronics , optics , physics , astrophysics , galaxy , composite material
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.