Atom transfer radical polymerization or #ATRP is a subset of controlled radical polymerization method to synthesize polymer with controlled molecular weight and defined architecture (1). It has been applied in industrial processes to produce materials for electronic and biological applications. #Irppy3 was demonstrated by the #hawker_group to mediate ATRP using photoredox catalysis (2). Motivated to replace the Ir PC to avoid metal contamination in the polymer, the #miyake_group has developed a series of organic dihydrophenazine (3) and phenoxazine (4) PC derivatives. Specifically, #PhenN_2Naph and #PhenO_1Naph_Biph were demonstrated as high-performing organic PCs capable of producing polymers with high initiator efficiencies and low dispersities.
References
(1) Matyjaszewski, K.; Xia, J., Atom Transfer Radical Polymerization. Chem. Rev. 2001, 101, 2921. Link
(2) Fors, B. P.; Hawker, C. J., Control of a Living Radical Polymerization of Methacrylates by Light. Angew. Chem. Int. Ed. 2012, 51, 8850. Link
(3) Theriot, J. C.; Lim, C.-H.; Yang, H.; Ryan, M. D.; Musgrave, C. B.; Miyake, G. M., Organocatalyzed atom transfer radical polymerization driven by visible light. Science 2016, 352, 1082. Link
(4) Pearson, R. M.; Lim, C.-H.; McCarthy, B. G.; Musgrave, C. B.; Miyake, G. M., Organocatalyzed Atom Transfer Radical Polymerization Using N-Aryl Phenoxazines as Photoredox Catalysts. J. Am. Chem. Soc. 2016, 138, 11399. Link
(5) Theriot, J. C.; McCarthy, B. G.; Lim, C.-H.; Miyake, G. M., Organocatalyzed Atom Transfer Radical Polymerization: Perspectives on Catalyst Design and Performance. Macromolecular Rapid Commun. 2017, 1700040. Link
(6) Discekici, E. H.; St. Amant, A. H.; Nguyen, S. N.; Lee, I.-H.; Hawker, C. J.; Read de Alaniz, J., Endo and Exo Diels–Alder Adducts: Temperature-Tunable Building Blocks for Selective Chemical Functionalization. J. Am. Chem. Soc. 2018, 140, 5009. Link
(7) Theriot, J. C.; Miyake, G. M.; Boyer, C. A., N,N-Diaryl Dihydrophenazines as Photoredox Catalysts for PET-RAFT and Sequential PET-RAFT/O-ATRP. ACS Macro Lett. 2018, 7, 662. Link