title: Visible-Light-Induced Click Chemistry.
abstract: A rapid and catalyst-free cycloaddition system for visible-light-induced click chemistry is reported. A readily accessible photoreactive 2H-azirine moiety was designed to absorb light at wavelengths above 400 nm. Irradiation with low-energy light sources thus enables efficient small-molecule synthesis with a diverse range of multiple-bond-containing compounds. Moreover, in order to demonstrate the efficiency of the current approach, quantitative ligation of the photoactivatable chromophore with functional polymeric substrates was performed and full conversion with irradiation times of only 1 min at ambient conditions was achieved. The current report thus presents a highly efficient method for applications involving selective cycloaddition to electron-deficient multiple-bond-containing materials.
authors.affiliation: Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76128 Karlsruhe (Germany).|Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen (Germany).
authors.forename: Jan O
authors.initials: JO
authors.lastname: Mueller
authors.affiliation: Evonik Industries AG, Paul-Baumann-Strasse 1, 45764 Marl (Germany).
authors.forename: Friedrich G
authors.initials: FG
authors.lastname: Schmidt
authors.affiliation: Queensland University of Technology, School of Chemistry, Physics and Mechanical Engineering, 2 George St, Brisbane, Queensland 4001 (Australia). j.blinco@qut.edu.au.
authors.forename: James P
authors.initials: JP
authors.lastname: Blinco
authors.affiliation: Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstrasse 18, 76128 Karlsruhe (Germany). christopher.barner-kowollik@kit.edu.|Institut für Biologische Grenzflächen, Karlsruhe Institute of Technology (KIT), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen (Germany). christopher.barner-kowollik@kit.edu.|Queensland University of Technology, School of Chemistry, Physics and Mechanical Engineering, 2 George St, Brisbane, Queensland 4001 (Australia). christopher.barner-kowollik@kit.edu.
authors.forename: Christopher
authors.initials: C
authors.lastname: Barner-Kowollik
mesh_terms: D002384:Catalysis; D057930:Click Chemistry; D008027:Light; D010777:Photochemistry; D011108:Polymers / Q000737:chemistry*
chemical_list: D011108:Polymers
keywords: azirine; click chemistry; photochemistry; polymer ligation; visible light