Recent development in halogen-bonding-catalyzed living radical polymerization

Wang, Chen‐Gang; Chong, Amerlyn Ming Liing; Pan, Houwen Matthew; Sarkar, Jit; Tay, Xiu Ting; Goto, Atsushi

doi:10.1039/d0py00939c

Cited by 57 publications

(59 citation statements)

References 138 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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“…The polymerization is initiated by halide abstraction using a XB donor (Scheme 10). Interestingly, while iodine(I) based XB donors have also been used in such a reaction a few years ago [96–98] diaryliodonium salts actually have a long history as photoacids of polymerization [99] . The use of the latter as Lewis acid in such a transformation was however never explored.…”

Section: Applications In Organocatalysismentioning

confidence: 99%

Iodine(III)‐Based Halogen Bond Donors: Properties and Applications

Robidas

Reinhard

Legault

et al. 2021

The Chemical Record

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Halogen bonding, the non‐covalent interaction of Lewis bases with an electron‐deficient region of halogen substituents, received increased attention recently. Consequently, the design and evaluation of numerous halogen‐containing species as halogen bond donors have been subject to intense research. More recently, organoiodine compounds at the iodine(III) state have been receiving growing attention in the field. Due to their electronic and structural properties, they provide access to unique binding modes. For this reason, our groups have been involved in the development of such compounds, in the quantification of their halogen bonding strength (through the evaluation of their Lewis acidities), as well as in the evaluation of their activities as catalysts in several model reactions. This account will describe these contributions.

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Recent development in halogen-bonding-catalyzed living radical polymerization

Abstract: The development and applications of an organocatalyzed living radical polymerization via halogen-bonding catalysis, i.e., reversible complexation mediated polymerization (RCMP), are highlighted.

Cited by 57 publications

References 138 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

Iodine(III)‐Based Halogen Bond Donors: Properties and Applications

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