Coumarinylmethyl Caging Groups with Redshifted Absorption |
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Authors: | Dr. Ludovic Fournier Dr. Isabelle Aujard Dr. Thomas Le Saux Sylvie Maurin Sandra Beaupierre Prof. Dr. Jean‐Bernard Baudin Prof. Dr. Ludovic Jullien |
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Affiliation: | 1. Ecole Normale Supérieure, Département de Chimie, UMR CNRS‐ENS‐UPMC, Paris 06 8640 PASTEUR, 24, rue Lhomond, 75231 Paris Cedex 05 (France);2. UPMC Paris 06, 4, Place Jussieu, 75232 Paris Cedex 05 (France) |
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Abstract: | 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. |
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Keywords: | caged compounds photochemistry photolysis protecting groups UV/Vis spectroscopy |
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