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

ABSTRACT: 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.

SUBMITTER: Klausen M

PROVIDER: S-EPMC6481246 | biostudies-literature | 2019 Apr

REPOSITORIES: biostudies-literature

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

Klausen Maxime M Dubois Victor V Clermont Guillaume G Tonnelé Claire C Castet Frédéric F Blanchard-Desce Mireille M

Chemical science 20190313 15

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 ...[more]

PMID: 31057749

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