Enlightening the Mechanism of Copper Mediated PhotoRDRP via High-Resolution Mass Spectrometry

Frick, Elena; Anastasaki, Athina; Haddleton, David M.; Barner‐Kowollik, Christopher

doi:10.1021/jacs.5b03048

Cited by 114 publications

(107 citation statements)

References 48 publications

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“…33 Additionally, electrochemical studies have shown RAFT agents similar to those employed herein (i.e. In a recent publication focused on elucidating the mechanism of Cu-based Pi-RDRP it was illustrated that electron transfer from an amine ligand identical to the amine employed in this study (i.e.…”

mentioning

confidence: 65%

Tertiary amine catalyzed photo-induced controlled radical polymerization of methacrylates

McKenzie

Tan

et al. 2015

Polym. Chem.

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A novel tertiary amine catalyst (TAC) and trithiocarbonate (TTC) synergistic photo-induced controlled radical polymerization of methacrylates in the absence of conventional photoinitiators, metal-catalysts, or dye sensitizers, has been realized under mild UV irradiation (λ max ≈ 365 nm), yielding polymethacrylates with low molecular weight distributions and excellent end-group fidelity (> 95%).

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mentioning

confidence: 65%

Tertiary amine catalyzed photo-induced controlled radical polymerization of methacrylates

McKenzie

Tan

et al. 2015

Polym. Chem.

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“…25 To realize a visible light absorbing PC we explored a core substituted phenoxazine derivative. Computations predicted that PC 5 , possessing 4-biphenyl core substitutions, would be an excellent target PC with 3 PC* possessing a strong reduction potential and spatially separated SOMOs, while 1 PC would exhibit an absorbance profile in the visible spectrum.…”

Section: Resultsmentioning

confidence: 99%

Organocatalyzed Atom Transfer Radical Polymerization Using N-Aryl Phenoxazines as Photoredox Catalysts

et al. 2016

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N-Aryl phenoxazines have been synthesized and introduced as strongly reducing metal-free photoredox catalysts in organocatalyzed atom transfer radical polymerization for the synthesis of well-defined polymers. Experiments confirmed quantum chemical predictions that, like their dihydrophenazine analogs, the photoexcited states of phenoxazine photoredox catalysts are strongly reducing and achieve superior performance when they possess charge transfer character. We compare phenoxazines to previously reported dihydrophenazines and phenothiazines as photoredox catalysts to gain insight into the performance of these catalysts and establish principles for catalyst design. A key finding reveals that maintenance of a planar conformation of the phenoxazine catalyst during the catalytic cycle encourages the synthesis of well-defined macromolecules. Using these principles, we realized a core substituted phenoxazine as a visible light photoredox catalyst that performed superior to UV-absorbing phenoxazines as well as previously reported organic photocatalysts in organocatalyzed atom transfer radical polymerization. Using this catalyst and irradiating with white LEDs resulted in the production of polymers with targeted molecular weights through achieving quantitative initiator efficiencies, which possess dispersities ranging from 1.13 to 1.31.

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“…The mechanism of photoATRP with Cu as the catalyst has been the subject of some debate . Although detailed discussions of the mechanism are beyond the scope of this review, we will briefly summarize some of the key features of this mechanism.…”

Section: Mechanistic Considerations In Photoinduced Atrp (Photoatrp)mentioning

confidence: 99%

Photochemistry for Well‐Defined Polymers in Aqueous Media: From Fundamentals to Polymer Nanoparticles to Bioconjugates

Burridge

Wright

Page

et al. 2018

Macromol. Rapid Commun.

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This review article highlights recent developments in the field of photochemistry and photochemical reversible deactivation radical polymerization applied to aqueous polymerizations. Photochemistry is a topic of significant interest in the fields of organic, polymer, and materials chemistry because it allows challenging reactions to be performed under mild conditions. Aqueous polymerization is of significant interest because water is an environmentally benign solvent, and the use of water enables complex polymer self-assembly and bioconjugation processes to occur. This review focuses on powerful new developments in photochemical aqueous polymerization reactions and their applications to the synthesis of well-defined polymer nano-objects and bioconjugates. It is anticipated that these aqueous photopolymerizations will enable the next generation of self-assembled structures and biohybrid materials to be developed under mild and environmentally friendly conditions.

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Enlightening the Mechanism of Copper Mediated PhotoRDRP via High-Resolution Mass Spectrometry

Cited by 114 publications

References 48 publications

Tertiary amine catalyzed photo-induced controlled radical polymerization of methacrylates

Tertiary amine catalyzed photo-induced controlled radical polymerization of methacrylates

Organocatalyzed Atom Transfer Radical Polymerization Using N-Aryl Phenoxazines as Photoredox Catalysts

Photochemistry for Well‐Defined Polymers in Aqueous Media: From Fundamentals to Polymer Nanoparticles to Bioconjugates

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