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Two-Photon “Caging” Groups: Effect of Position Isomery on the Photorelease Properties of Aminoquinoline-Derived Photolabile Protecting Groups

Abstract : High two-photon photolysis cross sections and water solubility of probes are important to avoid toxicity in biomedical applications of photolysis. Systematic variation of the position of a carboxyl electron-withdrawing group (EWG) on photolysis of 8-dimethylaminoquinoline protecting groups identified the C5-substituted isomer as a privileged dipole. The 5-benzoyl-8-DMAQ substitution yields a caging group with an enhanced two-photon uncaging cross section (δu = 2.0 GM) and good water solubility (c ≤ 50 mM, pH 7.4).
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02383361
Contributor : Thibault Gallavardin <>
Submitted on : Wednesday, November 27, 2019 - 4:53:22 PM
Last modification on : Tuesday, September 22, 2020 - 3:38:35 AM

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Christine Tran, Thibault Gallavardin, Morgane Petit, Riadh Slimi, Hamid Dhimane, et al.. Two-Photon “Caging” Groups: Effect of Position Isomery on the Photorelease Properties of Aminoquinoline-Derived Photolabile Protecting Groups. Organic Letters, American Chemical Society, 2015, 17 (3), pp.402-405. ⟨10.1021/ol5035035⟩. ⟨hal-02383361⟩

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