Photomediated core modification of organic photoredox catalysts in radical addition: mechanism and applications

Zhang, Yajun; Jiang, Daifeng; Fang, Zheng; Zhu, Ning; Sun, Naixian; He, Wei; Liu, Chengkou; Zhao, Lili; Guo, Kai

doi:10.1039/d1sc02258j

Cited by 17 publications

(13 citation statements)

References 49 publications

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“…88 In later work, it was shown that this core-substitution side reaction could be used to generate a series of new phenazine PCs and that coresubstitution could be used to tune several catalytically relevant properties. 89,90 3.3.3. Phenothiazines.…”

Section: Oxidative and Reductive Quenching Mechanismsmentioning

confidence: 91%

Photoinduced Organocatalyzed Atom Transfer Radical Polymerization (O-ATRP): Precision Polymer Synthesis Using Organic Photoredox Catalysis

2021

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The development of photoinduced organocatalyzed atom transfer radical polymerization (O-ATRP) has received considerable attention since its introduction in 2014. Expanding on many of the advantages of traditional ATRP, O-ATRP allows well-defined polymers to be produced under mild reaction conditions using organic photoredox catalysts. As a result, O-ATRP has opened access to a range of sensitive applications where the use of a metal catalyst could be of concern, such as electronics, certain biological applications, and the polymerization of coordinating monomers. However, key limitations of this method remain and necessitate further investigation to continue the development of this field. As such, this review details the achievements made to-date as well as future research directions that will continue to expand the capabilities and application landscape of O-ATRP. CONTENTS 4.5. Styrene and 4-Vinylpyridine 4.6. Vinyl Cyclopropanes 4.7. Other Monomers 5. Applications of O-ATRP 5.1. Synthesis of Block Copolymers 5.2. Synthesis of Graft Polymers 5.3. Synthesis of Hyperbranched Polymers 5.4. Synthesis of Star Polymers 5.5. Surface-initiated O-ATRP 5.6. Synthesis of Polymers in Continuous Flow 5.7. Metal Sensitive Applications of O-ATRP 6. Conclusions and Future Directions Author Information Corresponding Author Author Notes Biographies Acknowledgments References

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Section: Oxidative and Reductive Quenching Mechanismsmentioning

confidence: 91%

Photoinduced Organocatalyzed Atom Transfer Radical Polymerization (O-ATRP): Precision Polymer Synthesis Using Organic Photoredox Catalysis

2021

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“…Dihydrophenazines proved to exhibit both features and some progress has been reported. [21][22][23] Through computational design, the catalyst structure and the polymerization conditions have been optimized, achieving low Đ and tunable MWs upon activation/deactivation of the light source (Figure 1a). In parallel, the chemical modification of the phenoxazine family aimed for the same features.…”

Section: Organocatalyzed Photoredox Polymerizationmentioning

confidence: 99%

Spotting Trends in Organocatalyzed and Other Organomediated (De)polymerizations and Polymer Functionalizations

et al. 2022

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Organocatalysis has evolved into an effective complement to metal‐ or enzyme‐based catalysis in polymerization, polymer functionalization, and depolymerization. The ease of removal and greater sustainability of organocatalysts relative to transition‐metal‐based ones has spurred development in specialty applications, e.g., medical devices, drug delivery, optoelectronics. Despite this, the use of organocatalysis and other organomediated reactions in polymer chemistry is still rapidly developing, and we envisage their rapidly growing application in nascent areas such as controlled radical polymerization, additive manufacturing, and chemical recycling in the coming years. In this Review, we describe ten trending areas where we anticipate paradigm shifts resulting from novel organocatalysts and other transition‐metal‐free conditions. We highlight opportunities and challenges and detail how new discoveries could lead to previously inaccessible functional materials and a potentially circular plastics economy.

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“…Further attempts on improving catalyst performance focused on achieving strongly reducing excited states for the PCs and a shift towards visible‐light absorption. Dihydrophenazines proved to exhibit both features and some progress has been reported [21–23] . Through computational design, the catalyst structure and the polymerization conditions have been optimized, achieving low Đ and tunable MWs upon activation/deactivation of the light source (Figure 1a).…”

Section: Burgeoning Areas In Organocatalyzed and Other Transition‐met...mentioning

confidence: 99%

Spotting Trends in Organocatalyzed and Other Organomediated (De)polymerizations and Polymer Functionalizations

et al. 2022

View full text Add to dashboard Cite

Organocatalysis has evolved into an effective complement to metal-or enzyme-based catalysis in polymerization, polymer functionalization, and depolymerization. The ease of removal and greater sustainability of organocatalysts relative to transition-metal-based ones has spurred development in specialty applications, e.g., medical devices, drug delivery, optoelectronics. Despite this, the use of organocatalysis and other organomediated reactions in polymer chemistry is still rapidly developing, and we envisage their rapidly growing application in nascent areas such as controlled radical polymerization, additive manufacturing, and chemical recycling in the coming years. In this Review, we describe ten trending areas where we anticipate paradigm shifts resulting from novel organocatalysts and other transition-metalfree conditions. We highlight opportunities and challenges and detail how new discoveries could lead to previously inaccessible functional materials and a potentially circular plastics economy.

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Photomediated core modification of organic photoredox catalysts in radical addition: mechanism and applications

Abstract: Dihydrophenazines and their analogues have been widely used as strong reducing photoredox catalysts in radical chemistry, such as organocatalyzed atom transfer radical polymerization (O-ATRP). However, when dihydrophenazines were employed as...

Cited by 17 publications

References 49 publications

Photoinduced Organocatalyzed Atom Transfer Radical Polymerization (O-ATRP): Precision Polymer Synthesis Using Organic Photoredox Catalysis

Photoinduced Organocatalyzed Atom Transfer Radical Polymerization (O-ATRP): Precision Polymer Synthesis Using Organic Photoredox Catalysis

Spotting Trends in Organocatalyzed and Other Organomediated (De)polymerizations and Polymer Functionalizations

Spotting Trends in Organocatalyzed and Other Organomediated (De)polymerizations and Polymer Functionalizations

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