ESIPT-Capable 4-(2-Hydroxyphenyl)-2-(Pyridin-2-yl)-1H-Imidazoles with Single and Double Proton Transfer: Synthesis, Selective Reduction of the Imidazolic OH Group and Luminescence.

ABSTRACT: 1H-Imidazole derivatives establish one of the iconic classes of ESIPT-capable compounds (ESIPT = excited state intramolecular proton transfer). This work presents the synthesis of 1-hydroxy-4-(2-hydroxyphenyl)-5-methyl-2-(pyridin-2-yl)-1H-imidazole (L^OH,OH) as the first example of ESIPT-capable imidazole derivatives wherein the imidazole moiety simultaneously acts as a proton acceptor and a proton donor. The reaction of L^OH,OH with chloroacetone leads to the selective reduction of the imidazolic OH group (whereas the phenolic OH group remains unaffected) and to the isolation of 4-(2-hydroxyphenyl)-5-methyl-2-(pyridin-2-yl)-1H-imidazole (L^H,OH), a monohydroxy congener of L^OH,OH. Both L^OH,OH<

SUBMITTER: Shekhovtsov NA 

PROVIDER: S-EPMC9962989 | biostudies-literature | 2023 Feb

REPOSITORIES: biostudies-literature