Two-Photon Sensitive Coumarinyl Photoremovable Protecting Groups with Rigid Electron-Rich Cycles Obtained by Domino Reactions Initiated by a 5-exo-Dig Cyclocarbopalladation

We herein report the design, synthesis, and photophysical characterization of extended and rigid coumarinyl derivatives showing large two-photon sensitivities (δaΦu ≤ 125 GM) at 740 and 800 nm. To efficiently synthesize these complex photoremovable protecting groups (PPGs), we used step-economic dom...

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Bibliographic Details
Published in:Organic letters 2021-10, Vol.23 (19), p.7580-7585
Main Authors: Chaud, Juliane, Morville, Clément, Bolze, Frédéric, Garnier, Delphine, Chassaing, Stefan, Blond, Gaëlle, Specht, Alexandre
Format: Article
Language:English
Subjects:
Chemical Sciences
Engineering Sciences
Medicinal Chemistry
Optics
Organic chemistry
Photonic
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Summary:We herein report the design, synthesis, and photophysical characterization of extended and rigid coumarinyl derivatives showing large two-photon sensitivities (δaΦu ≤ 125 GM) at 740 and 800 nm. To efficiently synthesize these complex photoremovable protecting groups (PPGs), we used step-economic domino reactions. Moreover, those new coumarinyl PPGs display unique bathochromic shifts (≤100 nm) of the uncaging subproducts as a result of the formation of a more conjugated fulvene moiety.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02778