Recent progress in the applications of amino–yne click chemistry

Zhang, Jie; Zhang, Zhiming; Wang, Jia; Zang, Qiguang; Sun, Jingzhi; Tang, Ben Zhong

doi:10.1039/d1py00113b

Cited by 29 publications

(18 citation statements)

References 70 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The incorporation of these functional groups opens up a wide range of possibilities for the further transformation of the polymers by application of such REO (robust, efficient, and orthogonal) chemistries as azide–alkyne cycloadditions, thiol–ene, thiol–yne, and amino–yne reactions. − …”

Section: Resultsmentioning

confidence: 99%

One-Step, Room Temperature Synthesis of Well-Defined, Organo-Soluble Multifunctional Aromatic Polyimides

et al. 2021

View full text Add to dashboard Cite

Efficient and ambient synthesis of aromatic polyimides (PIs) from readily available starting materials remains a very challenging task in polymer chemistry. Herein, we report for the first time a robust, one-step synthesis of organo-soluble functional aromatic PIs. Room temperature, metal-free, superacid (TFSA)-catalyzed step polymerization of aryl-terminated diimides with carbonyl compounds (2,2,2-trifluoroacetophenone and indoline-2,3-dione (isatin)) afforded 14 high-molecular-weight, linear, film-forming PIs. The effect of structural variation of the dianhydride segment, the amount of catalyst, and monomer concentration were studied. The PIs were obtained in quantitative yields, with high thermal stabilities up to 525 °C and 55% weight residue at 800 °C under an inert atmosphere and number-average molecular weights (M n) in a range of 51–195 kg mol–1. Well-controlled proportions of the functional phenolic hydroxyl groups (at the ortho-position to the imide ring) and diaryloxindole reactive sites were introduced into macromolecules during polyimide syntheses, while pendent allyl and propargyl groups were formed by the chemical postpolymerization reactions. Subsequent modifications of the reactive sites using click-chemistry can afford multifunctional polymers with tunable properties. The thermal postpolymerization modification of polyhydroxyimides converts them into polybenzoxazoles (so-called thermally rearranged polymers).

show abstract

Section: Resultsmentioning

confidence: 99%

One-Step, Room Temperature Synthesis of Well-Defined, Organo-Soluble Multifunctional Aromatic Polyimides

et al. 2021

View full text Add to dashboard Cite

show abstract

“…Taking advantage of its high efficiency, this amino‐yne click polymerization has attracted researchers' attention from various fields, such as surface immobilization and modification, drug delivery, synthesis of hydrogel and macromolecular materials. [ 49 ]…”

Section: Polymerization Of Mono‐activated Internal Alkynesmentioning

confidence: 99%

Activated Internal Alkyne‐Based Polymerization^†

Wang

et al. 2022

Chin. J. Chem.

Self Cite

View full text Add to dashboard Cite

As an emerging and efficient polymerization methodology, activated internal alkyne-based polymerization has been considered as a powerful tool for the construction of polymers with diverse architectures and versatile functions. This review focuses on the recent progresses in the polymerization using mono-activated, di-activated, in-situ generated, ring-strained ethynyl groups as substrates, coupling with post-modification on premade polymers containing activated internal ethynyl moieties. Representative examples are used to illustrate the fundamental design strategy, the development of polymerization and post-functionalization, along with the properties and potential applications of the prepared polymers. Moreover, the challenges and perspectives in terms of new-type active alkynes, green polymerization methodology, tailored regio-/stereoselectivity modulation, and potentially expanded application in this area are also discussed.

show abstract

“…It should be noted that the question of a meaningful definition of “click chemistry” in connection with polymer synthesis and post‐polymerization modifications deserves caution 134 . In polymer chemistry, the list of available “click” reactions is far longer than that in Table 1 and it comprises Diels‐Alder, Alder‐ene, thio‐bromo, 1,2,4‐triazoline‐3,5‐dione, amino‐yne, and boronic acid‐based chemistry 135–137 . Our feeling, then, is that the potential of “click” reactions in the field of MSR polymers, granted by the orthogonality of these reactions, is not fully deployed to‐date.…”

Section: Click and Other Reactions For Post‐polymerization Assembly And Modificationsmentioning

confidence: 99%

Playing construction with the monomer toy box for the synthesis of multi‐stimuli responsive copolymers by reversible deactivation radical polymerization protocols

D’Acunzo

Masci

2021

Journal of Polymer Science

View full text Add to dashboard Cite

In this review article, we survey the 2016–June 2021 scientific literature on the synthesis of multi‐stimuli responsive (MSR) polymers, the main focus being on reversible deactivation radical polymerization techniques (RDRPs, also known as controlled radical polymerizations). In fact, along more than 40 years of extensive research, RDRPs have boosted the synthesis of stimuli‐responsive polymers. RDRPs are now robust, versatile, relatively user‐friendly and even interconvertible, thus allowing control over composition, sequence, and topology of polymers. Such control can afford materials with well‐defined responses to physical, chemical, and biological external stimuli. Furthermore, “click” reactions are used to combine macromolecular precursors or to introduce specific functional groups in the target structure. As a result, MSR polymers are obtained from diverse combinations of commercial or specially synthesized building blocks arranged at will into desired sequences and architectures. Thanks to this versatility, self‐assembling polymeric structures are designed either to respond to triggers and perform specific applicative tasks, or to investigate the influence of structural variables on the responsivity of polymers. The “green” trend emerging in the field of responsive polymers and RDRPs is also briefly discussed.

show abstract

Recent progress in the applications of amino–yne click chemistry

Abstract: Click chemistry has been rapidly developed in recent years. Among various classical or newly established click systems, spontaneous amino-yne click reaction stands out. In addition to the general advantages belonging...

Cited by 29 publications

References 70 publications

One-Step, Room Temperature Synthesis of Well-Defined, Organo-Soluble Multifunctional Aromatic Polyimides

One-Step, Room Temperature Synthesis of Well-Defined, Organo-Soluble Multifunctional Aromatic Polyimides

Activated Internal Alkyne‐Based Polymerization^†

Playing construction with the monomer toy box for the synthesis of multi‐stimuli responsive copolymers by reversible deactivation radical polymerization protocols

Contact Info

Product

Resources

About

Recent progress in the applications of amino–yne click chemistry

Abstract: Click chemistry has been rapidly developed in recent years. Among various classical or newly established click systems, spontaneous amino-yne click reaction stands out. In addition to the general advantages belonging...

Cited by 29 publications

References 70 publications

One-Step, Room Temperature Synthesis of Well-Defined, Organo-Soluble Multifunctional Aromatic Polyimides

One-Step, Room Temperature Synthesis of Well-Defined, Organo-Soluble Multifunctional Aromatic Polyimides

Activated Internal Alkyne‐Based Polymerization†

Playing construction with the monomer toy box for the synthesis of multi‐stimuli responsive copolymers by reversible deactivation radical polymerization protocols

Contact Info

Product

Resources

About

Activated Internal Alkyne‐Based Polymerization^†