Issue 15, 2019
From the journal:

Chemical Science

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

Maxime Klausen,*a   Victor Dubois,a   Guillaume Clermont,a   Claire Tonnelé, ORCID logo a   Frédéric Castet ORCID logo a  and  Mireille Blanchard-Desce ORCID logo *a  

* Corresponding authors

a Univ. Bordeaux, Institut des Sciences Moléculaires (UMR5255 CNRS), 351 cours de la Libération, Talence, France
E-mail: mireille.blanchard-desce@u-bordeaux.fr

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.

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

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Article information

DOI
https://doi.org/10.1039/C9SC00148D
Article type
Edge Article
Submitted
10 Jan 2019
Accepted
02 Mar 2019
First published
13 Mar 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 4209-4219

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

M. Klausen, V. Dubois, G. Clermont, C. Tonnelé, F. Castet and M. Blanchard-Desce, Chem. Sci., 2019, 10, 4209 DOI: 10.1039/C9SC00148D

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