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Article Dans Une Revue Chemical Science Année : 2019

Dual-wavelength efficient two-photon photorelease of glycine by π-extended dipolar coumarins

Résumé

Photolabile protecting groups (PPGs) releasing bioactive compounds upon two-photon excitation have emerged as increasingly popular tools to control and study physiological processes. Yet the limited two-photon photosensitivity of many cages is still a critical issue for applications. We herein report the design, synthesis and photophysical study of polarized extended coumarinyl derivatives which show large two-photon sensitivity (up to 440 GM) at two complementary wavelengths in the NIR spectral range. DFT calculations demonstrate that subtle tuning of polarization in the ground-state and confinement of the photo-induced intramolecular charge transfer upon excitation is responsible for enhancing two-photon absorption while maintaining large uncaging efficiency. These findings open a new engineering route towards efficient coumarinyl PPGs

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Chimie
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Dates et versions

hal-02416878 , version 1 (17-01-2023)

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Maxime Klausen, Victor Dubois, Guillaume Clermont, Claire Tonnelé, Frédéric Castet, et al.. Dual-wavelength efficient two-photon photorelease of glycine by π-extended dipolar coumarins. Chemical Science, 2019, 10 (15), pp.4209-4219. ⟨10.1039/C9SC00148D⟩. ⟨hal-02416878⟩
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