Multi-responsive γ-methylene-γ-butyrolactone/<i>N</i>-vinyl caprolactam copolymers involving pH-dependent reversible lactonization

Wang, Zhuoqun; Debuigne, Antoine

doi:10.1039/d2py00713d

Cited by 1 publication

(2 citation statements)

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“…Hydrolysis of their pendant lactones produced unique stimuli responsive materials including pH-sensitive hydroxy acid-functional poly(vinyl alcohol) (PVOHs) 99 as well as dual pH/thermo-responsive hydroxy acid-bearing PNVCLs. 100 In contrast to the previously reported acid-functional PNVCLs, this multi-responsive NVCLbased system emphasized a unique reversible pH-dependent ring opening/closure of the pendant lactones preventing aggregation via H-bonding upon reacidification.…”

Section: [-O] Methylene Cyclic Estermentioning

confidence: 88%

“…From there, the five membered ring -methylene--butyrolactone (MBL) 32, a non-conjugated version of 1 and a cyclic structural analog of VAc, was prepared by Pd-catalyzed cycloisomerization of 4-pentyn-1oic acid and used as comonomer in radical polymerizations for incorporating pendant lactones within LAMs-based copolymers (Figure 27). 99,100 The radical polymerization of 32 exclusively proceeded via rRRP and its organometallic-mediated radical copolymerization with VAc 99 or N-vinyl caprolactam (NVCL) 100 led to a series of well-defined MBL-containing copolymers with controlled compositions. Hydrolysis of their pendant lactones produced unique stimuli responsive materials including pH-sensitive hydroxy acid-functional poly(vinyl alcohol) (PVOHs) 99 as well as dual pH/thermo-responsive hydroxy acid-bearing PNVCLs.…”

Section: [-O] Methylene Cyclic Estermentioning

confidence: 99%

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Radical Polymerization of Methylene Heterocyclic Compounds: Functional Polymer Synthesis and Applications

Wang

Debuigne

2023

Polymer Reviews

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Synthetic polymers sustain a wide range of applications but the quest for further sophistication and functionalization of polymers remains topical to improve their scope and performance. In this respect, the radical polymerization of exo-methylene heterocyclic compounds (MHCs) is attractive. Compared to the classical acyclic vinyl monomers constrained to the vinyl-type polymerization process, MHCs can undergo different polymerization modes, namely the radical ring-retaining polymerization (rRRP) and the radical ring-opening polymerization (rROP). In rRRP, the cyclic group is preserved and inserted as side group of the polymer backbone offering a myriad of post-polymerization modifications whereas functional groups are incorporated within the backbone of linear polymers and confer them some degradability in rROP. Herein, recent advances in the radical polymerization of MHCs as well as the variety of macromolecular structures and applications it offers are highlighted. The reversible deactivation radical polymerization of MHCs leading to well-defined MHC-based macromolecular architectures, including multifunctional, stimuli-responsive and degradable polymers, is also discussed. The review emphasizes the current limitations of the radical polymerization of MHCs as well as future prospects including the development of innovative bio-based MHCs. Overall, the radical polymerization of MCHs represents a powerful macromolecular engineering tool and a broad field of exploration for polymer chemists. clothing, adhesives, etc, to highly engineered polymers applied in medical, electronic and photonic technologies, to name a few. After several decades of progress, efforts to make polymerization techniques more efficient, versatile and sustainable, remain timely owing the increasing demand for innovative functional polymers able to address the requirements of today's applications.Free radical polymerization (FRP) is one of the most widely used polymerization methods.It proceeds through a classic chain growth process and generates high molecular weight polymers. Its robustness, tolerance to moisture and high compatibility with many functional groups, make radical polymerization a tool of choice for producing synthetic polymers, especially in industry. 1 However, the inherent irreversible termination reactions leading to illdefined structures prevent conventional FRP from being further used in cutting-edge applications which often require precise polymer architectures, predictable molecular weight and/or controlled chain-end functionalities.In the past decades, the limitations of conventional free radical polymerization have been overcome by the development of controlled radical polymerization, preferentially referred to as reversible deactivation radical polymerization (RDRP). 2 In the latter, a controlling agent allows the temporary deactivation of the propagating radicals in the form of a dormant species which limits the extent of irreversible reactions and prolongs the life time of radicals.In other words, a dynamic equilibr...

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Section: [-O] Methylene Cyclic Estermentioning

confidence: 88%

Section: [-O] Methylene Cyclic Estermentioning

confidence: 99%

Radical Polymerization of Methylene Heterocyclic Compounds: Functional Polymer Synthesis and Applications

Wang

Debuigne

2023

Polymer Reviews

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Multi-responsive γ-methylene-γ-butyrolactone/N-vinyl caprolactam copolymers involving pH-dependent reversible lactonization

Abstract: Poly(N-vinyl caprolactam) is one of the most popular thermo-responsive polymers used in the biomedical field. For application purposes, its transition temperature can be adjusted by copolymerizing N-vinyl caprolactam with comonomers...

Cited by 1 publication

References 62 publications

Radical Polymerization of Methylene Heterocyclic Compounds: Functional Polymer Synthesis and Applications

Radical Polymerization of Methylene Heterocyclic Compounds: Functional Polymer Synthesis and Applications

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