Fully oxygen-tolerant atom transfer radical polymerization triggered by sodium pyruvate

Szczepaniak, Grzegorz; Łagodzińska, Matylda; Dadashi‐Silab, Sajjad; Gorczyński, Adam; Matyjaszewski, Krzysztof

doi:10.1039/d0sc03179h

Cited by 59 publications

(58 citation statements)

References 90 publications

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“…The preparation of polymers with precise structure by photosynthesis is ubiquitous in nature. [ 1,2 ] Photo‐controlled reversible‐deactivation radical polymerization (RDRP) techniques, represented by atom transfer radical polymerization (ATRP), [ 3–6 ] reversible addition‐fragmentation chain‐transfer (RAFT) polymerization, [ 7–9 ] nitroxide‐mediated polymerization, [ 10 ] and reversible complexation‐mediated radical polymerization, [ 11–15 ] have made great advancement for the construction of various functional polymers with pre‐designable molecular weight and narrow molecular weight distribution. [ 16,17 ] Due to the mild polymerization condition, low side reaction and spatiotemporal control of photo‐controlled RDRP techniques, [ 18,19 ] various polymerization strategies have been developed including oxygen‐tolerance radical polymerization or using oxygen as co‐catalysts, [ 20–23 ] metal‐free radical polymerization under visible light even near‐infrared lights, [ 24–27 ] and photo/electro mediated sequential polymerization.…”

Section: Introductionmentioning

confidence: 99%

Visible Light‐Regulated Heterogeneous Catalytic PET‐RAFT by High Crystallinity Covalent Organic Framework

Lü

Yang

et al. 2021

Macromol. Rapid Commun.

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Covalent organic frameworks (COFs) are a class of promising photocatalysts for conversing light energy into chemical energy. Based on the tunable building blocks, COFs can be well‐designed as photocatalyst for mediating reversible addition‐fragmentation chain‐transfer (RAFT) polymerization. Herein, 1,3,6,8‐tetrakis(4‐formylphenyl)pyrene (TFPPy) and 2,2″‐bipyridine‐5,5″‐diamine (Bpy) are chosen to construct imine‐based TFPPy‐Bpy‐COFs for catalyzing RAFT polymerization of methacrylates under white light irradiation. The well‐defined polymers with precise molecular weight and narrow molecular weight distribution are obtained. The switch on/off light experiments suggest excellent temporal control toward RAFT polymerization system and the chain‐extension reaction indicates high chain‐end fidelity of macro‐initiators. Mechanism study clarifies that the electron transfer between excited state of TFPPy‐Bpy‐COFs and RAFT agent can form living radicals to mediate polymerization. This methodology provides a novel platform for reversible‐deactivation radical polymerization using COFs as heterogeneous catalysts.

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Section: Introductionmentioning

confidence: 99%

Visible Light‐Regulated Heterogeneous Catalytic PET‐RAFT by High Crystallinity Covalent Organic Framework

Lü

Yang

et al. 2021

Macromol. Rapid Commun.

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“…Inspired by research from Fu, 205 Goto, 191,206 Zhu 207 and Matyjaszewski's 208 on iodine‐mediated photoATRP, Lei and coworkers developed an innovative approach that took advantage of organocatalysts and sodium iodide (NaI) under white LED irradiation to catalyze ROP and iodine‐mediated photoATRP, respectively 44 . Simultaneously, it was demonstrated that 1,1,3,3‐tetramethylguanidine (TMG) organocatalysts combined with NaI could facilitate ROP of cyclic ester monomers like the LLA and photoATRP initiated from difunctional initiators such as 2‐hydroxyethyl‐2‐bromo‐2‐phenylacetate (Br‐Ph‐OH; Figure 21).…”

Section: Polymerization Methodologies Mediated Using Orthogonal External Stimulimentioning

confidence: 99%

Orthogonal synthesis and modification of polymer materials

Shahrokhinia

Biswas

Reuther

2021

Journal of Polymer Science

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In this review, we detail the progress throughout the years toward developing truly orthogonal polymerization mechanisms and modification procedures en route to complex macromolecular structures built from synthetic polymer materials. The orthogonal modifications of polymer side‐chains and end‐groups via sequential click reactions is described providing post‐polymerization routes to functional materials and unique polymer topologies. Further, historical and modern orthogonal polymerization methodologies are thoroughly reviewed showing the evolution of the field through the decades long study of selective polymerization mechanisms that provide unique copolymer structures that are typically difficult to achieve. These include the combinations of reversible deactivation radical polymerization mechanisms with a variety of polymerization mechanisms including ring opening polymerizations, ring opening metathesis polymerizations, and cationic polymerizations, to name a few.

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“…[19][20][21][22] Other effective methods include the use of photoredox catalysts, [23][24][25][26][27] electrochemical ATRP (eATRP), [28] and photoinduced initiators for continuous activator regeneration (PICAR) ATRP. [29] In ATRP and reversible addition-fragmentation chain transfer (RAFT) polymerization, enzymes such as glucose oxidase were added to convert O 2 to inert species. [30][31][32][33][34] Air-tolerant photocatalyzed RAFT polymerizations were also reported.…”

Section: Introductionmentioning

confidence: 99%

Air‐Tolerant Reversible Complexation Mediated Polymerization (RCMP) Using Aldehyde

Mao

Tay

Sarkar

et al. 2022

Macromol. Rapid Commun.

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An air‐tolerant reversible complexation mediated polymerization (RCMP) technique, which can be carried out without prior deoxygenation, is developed. The system contains a monomer, an alkyl iodide initiating dormant species, air (oxygen), an aldehyde, N‐hydroxyphthalimide (NHPI), and a base. Oxygen is consumed via the NHPI‐catalyzed conversion of the aldehyde (RCHO) to a carboxylic acid (RCOOH). The generated RCOOH is further converted to a carboxylate anion (RCOO−) by the base. The RCOO− generated in situ works as an RCMP catalyst; the polymerization proceeds with the monomer, alkyl iodide dormant species, and RCOO− catalyst. Thus, the system is not only air‐tolerant but also does not require additional RCMP catalysts, which is a notable feature of this system. (NHPI is used as an oxidation catalyst for converting RCHO to RCOOH.) This technique is amenable to methyl methacrylate, butyl methacrylate, benzyl methacrylate, 2‐hydroxyethyl methacrylate, and styrene, yielding polymers with relatively low‐dispersity (Mw/Mn = 1.20−1.49), where Mw and Mn are the weight‐ and number‐average molecular weights, respectively.

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Fully oxygen-tolerant atom transfer radical polymerization triggered by sodium pyruvate

Abstract: A novel photoinduced ATRP system enabling a well-controlled polymerization in both aqueous and organic solvents in an ambient atmosphere.

Cited by 59 publications

References 90 publications

Visible Light‐Regulated Heterogeneous Catalytic PET‐RAFT by High Crystallinity Covalent Organic Framework

Visible Light‐Regulated Heterogeneous Catalytic PET‐RAFT by High Crystallinity Covalent Organic Framework

Orthogonal synthesis and modification of polymer materials

Air‐Tolerant Reversible Complexation Mediated Polymerization (RCMP) Using Aldehyde

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