Luminescent two-way reversible shape memory polymers prepared by hydroxyl–yne click polymerization

Wang, Kaojin; Si, Han; Wan, Qing; Wang, Zhiming; Qin, Anjun; Tang, Ben Zhong

doi:10.1039/d0tc03888a

Cited by 25 publications

(20 citation statements)

References 65 publications

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“…There is also one example of a network polymer where a 4-armed hydroxy-terminated polycaprolactone macromonomer was reacted with bispropiolate monomers at ambient temperature to afford luminescent gels (Figure 14). 247 A functionalization reaction of hydroxypropylcellulose (HPC) with an ynone substrate catalyzed by DMAP proceeded at ambient temperature in good yield (Scheme 31). 199…”

Section: Applications In Polymer Chemistrymentioning

confidence: 99%

“…Highly cross-linked network polymers from hydroxyl-yne click polymerizations between an alcohol-terminated four-armed macromonomer and bis-propiolates . (a) Synthesis of PCL 3600 network from alkyl propiolate and (b) luminescent PCL 5800 network from tetraphenylethylene bis-propiolate.…”

Section: Hydroxyl-yne Reactionsmentioning

confidence: 99%

“…(a) Synthesis of PCL 3600 network from alkyl propiolate and (b) luminescent PCL 5800 network from tetraphenylethylene bis-propiolate. Reproduced with permission from ref . Copyright 2020 Royal Society of Chemistry.…”

Section: Hydroxyl-yne Reactionsmentioning

confidence: 99%

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Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-yne, Amino-yne, and Hydroxyl-yne Reactions from (Bio)Organic to Polymer Chemistry

et al. 2021

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The 1,4-conjugate addition reaction between activated alkynes or acetylenic Michael acceptors and nucleophiles (i.e., the nucleophilic Michael reaction) is a historically useful organic transformation. Despite its general utility, the efficiency and outcomes can vary widely and are often closely dependent upon specific reaction conditions. Nevertheless, with improvements in reaction design, including catalyst development and an expansion of the substrate scope to feature more electrophilic alkynes, many examples now present with features that are congruent with Click chemistry. Although several nucleophilic species can participate in these conjugate additions, ubiquitous nucleophiles such as thiols, amines, and alcohols are commonly employed and, consequently, among the most well developed. For many years, these conjugate additions were largely relegated to organic chemistry, but in the last few decades their use has expanded into other spheres such as bioorganic chemistry and polymer chemistry. Within these fields, they have been particularly useful for bioconjugation reactions and step-growth polymerizations, respectively, due to their excellent efficiency, orthogonality, and ambient reactivity. The reaction is expected to feature in increasingly divergent application settings as it continues to emerge as a Click reaction.

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Section: Applications In Polymer Chemistrymentioning

confidence: 99%

Section: Hydroxyl-yne Reactionsmentioning

confidence: 99%

See 1 more Smart Citation

Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-yne, Amino-yne, and Hydroxyl-yne Reactions from (Bio)Organic to Polymer Chemistry

et al. 2021

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“…39,40 In particular, except for linear and homoarm star oligomers, the unprecedented miktoarm star oligomer was also constructed through the combination of the convergent and divergent synthetic strategies in an overall 68% yield, which could serve as a newtype topological digital macromolecule to achieve 2D information matrix encoding for information encryption. Apart from linear and star polymers, this DABCO-catalyzed hydroxyl-yne click polymerization was also used to construct polymer networks 41 and hyperbranched polymers. 42 For example, Qin and Tang et al successfully constructed a luminescent two-way shape memory polymer network by polymerization of dipropiolates and 4-arm poly(-caprolactone)s (PCLs) terminated with hydroxyl groups (Figure 2C).…”

Section: Scheme 2 Examples Of Established Hydroxyl-yne Click Polymeri...mentioning

confidence: 99%

X-Yne Click Polymerization

Qin

Tang

2022

Preprint

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Alkyne-based click polymerizations have been nurtured into a powerful synthetic technique for the synthesis of new polymers with advanced structures and versatile functionalities. Among them, the emerging thiol-yne, hydroxyl-yne and amino-yne click polymerizations have made remarkable progresses from reactions to applications. All three polymerizations avoid the usage of inherently dangerous monomer and are safer to operate than the classical azide-alkyne click polymerization, making them more prospective for widespread applications. To greatly promote the new alkyne-based click polymerizations beyond the azide-alkyne click polymerization, we propose a new concept of “X-yne click polymerization” to unify them. In this Perspective, we mainly give a brief account of the progression of X-yne click polymerization and discuss in detail the challenges and opportunities in this field.

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“…SME is mainly achieved by designing physical or chemical cross-linking points between molecular chains and movable linear molecular chains. More and more SMPs have been endowed with new SEM and multi-functionality [39], breaking through the limitation of traditional concept, including multi-SME [40][41][42], two-way SME [43,44], new actuation methods and multifunctional shape memory composites by adding functional particles to achieve enhanced functions and remote controlling actuation under different conditions [45][46][47]. In fact, the emergence of shape memory composites promotes the rapid development of SMPs.…”

Section: Shape Memory Polymersmentioning

confidence: 99%

Shape Memory Polymer Fibers: Materials, Structures, and Applications

et al. 2021

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Shape memory polymer (SMP) is a kind of material that can sense and respond to the changes of the external environment, and its behavior is similar to the intelligent reflection of life. Electrospinning, as a versatile and feasible technique, has been used to prepare shape memory polymer fibers (SMPFs) and expand their structures. SMPFs show some advanced features and functions in many fields. In this review, we give a comprehensive overview of SMPFs, including materials, fabrication methods, structures, multifunction, and applications. Firstly, the mechanism and characteristics of SMP are introduced. We then discuss the electrospinning method to form various microstructures, like non-woven fibers, core/shell fibers, hollow fibers and oriented fibers. Afterward, the multiple functions of SMPFs are discussed, such as multi-shape memory effect, reversible shape memory effect and remote actuation of composites. We also focus on some typical applications of SMPFs, including biomedical scaffolds, drug carriers, self-healing, smart textiles and sensors, as well as energy harvesting devices. At the end, the challenges and future development directions of SMPFs are proposed.

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Luminescent two-way reversible shape memory polymers prepared by hydroxyl–yne click polymerization

Abstract: Two-way reversible shape memory polymers (2W-SMPs), capable of changing their shapes reversibly, are highly desirable for many potential applications. However, the polymerization reactions used for preparing 2W-SMPs always require harsh...

Cited by 25 publications

References 65 publications

Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-yne, Amino-yne, and Hydroxyl-yne Reactions from (Bio)Organic to Polymer Chemistry

Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-yne, Amino-yne, and Hydroxyl-yne Reactions from (Bio)Organic to Polymer Chemistry

X-Yne Click Polymerization

Shape Memory Polymer Fibers: Materials, Structures, and Applications

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