%0 Journal Article %A Tran, Christine %A Gallavardin, Thibault %A Petit, Morgane %A Slimi, Riadh %A Dhimane, Hamid %A Blanchard-Desce, Mireille %A Acher, Francine C. %A Ogden, David %A Dalko, Peter I. %D 2015 %T Two-Photon “Caging” Groups: Effect of Position Isomery on the Photorelease Properties of Aminoquinoline-Derived Photolabile Protecting Groups %U https://acs.figshare.com/articles/journal_contribution/Two_Photon_Caging_Groups_Effect_of_Position_Isomery_on_the_Photorelease_Properties_of_Aminoquinoline_Derived_Photolabile_Protecting_Groups/2208730 %R 10.1021/ol5035035.s001 %2 https://ndownloader.figshare.com/files/3844261 %K photolysi %K water solubility %K section %K EWG %K GM %X 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). %I ACS Publications