Synthesis and properties of couplable ABCDE star copolymers by orthogonal CuAAC and Diels–Alder click reactions

Liu, Huanhuan; Pan, Weidong; Tong, Min; Zhao, Youliang

doi:10.1039/c5py01960e

Cited by 19 publications

(6 citation statements)

References 83 publications

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“…Further, Liu et al carried out a synthetic method to obtain a 5‐arm miktoarm star copolymer via one‐pot orthogonal CuAAC/DA click reactions 40 . The ABCDE miktoram star comprised of PCL (A), (PtBA, B), poly( l ‐lactide) (PLLA) (C), PNIPAM (D) and poly(5‐methyl‐5‐allyloxycarbonyl‐1,3‐dioxane‐2‐one) (PMAC), E) arms was prepared by a strategy referred to as one‐pot “1 + 2 + 2”.…”

Section: Orthogonal Click Reactions In Polymer Synthesismentioning

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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Section: Orthogonal Click Reactions In Polymer Synthesismentioning

confidence: 99%

Orthogonal synthesis and modification of polymer materials

Shahrokhinia

Biswas

Reuther

2021

Journal of Polymer Science

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“…The strategies of star polymer synthesis have also been extended to double-click and triple-click approaches where combinations of CuAAC/Diels-Alder [181,182], (Fig. 16) CuAAC/thiol-ene [183], thiol-para-fluoro/thiol-ene [184] and CuAAC/Diels-Alder/thiol-ene [185] reactions were successfully employed in tailor-made architecturing.…”

Section: Star Polymersmentioning

confidence: 99%

Click Chemistry in Macromolecular Design: Complex Architectures from Functional Polymers

Arslan

Taşdelen

2018

Chemistry Africa

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This contribution reviews the applications of click chemistry reactions in design and synthesis of various macromolecular architectures that hold key aspects in polymer science. By considering the emerging concepts that shape how synthetic polymer chemistry and macromolecular engineering utilize 'reactions' in 'fabrication', in the last decade, the click chemistry methodologies have been pioneered the chemical approaches that allow to access diverse complex macromolecules. The common and leading features of click chemistry reactions rely on efficient, fast, selective and easy to implement chemical transformations giving very high to quantitative coupling efficiencies. These are essential virtues that provide triumphing in macromolecular engineering, since the building blocks are usually large polymer chains. For the efficient building of complex macromolecules via click reactions, properly functionalized polymers are key components in which special design is required to successful installation of 'clickable' reactive groups on polymer end groups or side chains. In this report, the synthetic methods encompassing various click chemistry reactions in fabrication and applications of a range of complex macromolecular architectures have been reviewed.

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“…The Diels‐Alder (DA) [4+2] cycloaddition reaction that occurs between an electron rich diene and an electron deficient dienophile was discovered by Otto Diels and Kurt Alder in 1928. Since its discovery, the reaction has been traditionally used in synthesis of complex natural products, and more recently has become a tool for synthesis of various functional materials and polymers . Interestingly, above a certain temperature, the DA cycloadduct readily undergoes the reverse fragmentation through the so‐called retro Diels‐Alder (rDA) reaction (Figure ).…”

Section: The Diels‐alder Reaction Based Protection‐deprotection Sequencementioning

confidence: 99%

The Taming of the Maleimide: Fabrication of Maleimide‐Containing ‘Clickable’ Polymeric Materials

Sanyal

2017

The Chemical Record

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Functional polymers are widely employed in various areas of biomedical sciences. In order to tailor them for desired applications, facile and efficient functionalization of these polymeric materials under mild and benign conditions is important. Polymers containing reactive maleimide groups can be employed for such applications since they provide an excellent handle for conjugation of thiol- and diene-containing molecules and biomolecules. Until recently, fabrication of maleimide containing polymeric materials has been challenging due to the interference from the highly reactive double bond. A Diels-Alder/retro Diels-Alder reaction sequence based strategy to transiently mask the maleimide group provides access to such polymeric materials. In this personal account, we summarize contributions from our group towards the fabrication and functionalization of maleimide-containing polymeric materials over the past decade.

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Synthesis and properties of couplable ABCDE star copolymers by orthogonal CuAAC and Diels–Alder click reactions

Abstract: Well-defined ABCDE star quintopolymers generated by a modular and orthogonal strategy could self-assemble into intriguing nanoobjects sensitive to thermal and pH stimuli.

Cited by 19 publications

References 83 publications

Orthogonal synthesis and modification of polymer materials

Orthogonal synthesis and modification of polymer materials

Click Chemistry in Macromolecular Design: Complex Architectures from Functional Polymers

The Taming of the Maleimide: Fabrication of Maleimide‐Containing ‘Clickable’ Polymeric Materials

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