Copper‐Free Synthesis of Glycidyl Triazolyl Polymers

Ikeda, Taichi

doi:10.1002/macp.201800147

Cited by 5 publications

(2 citation statements)

References 35 publications

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“…Ikeda continued the above work, in an attempt to introduce different types of substituents via the azide-alkyne reaction [120]. An interesting feature of this report is that by using prop-2-ynoic acid and but-2-ynedioic acid esters rather than species, in which the alkyne group was attached to an alkyl chain, it was possible to forego the copper catalyst used in the authors' previous work.…”

Section: Other Applications and Modifications Of Gapmentioning

confidence: 89%

Glycidyl Azide Polymer and its Derivatives-Versatile Binders for Explosives and Pyrotechnics: Tutorial Review of Recent Progress

Jarosz

Stolarczyk

Wawrzkiewicz-Jałowiecka

et al. 2019

Molecules

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Glycidyl azide polymer (GAP), an energetic binder, is the focus of this review. We briefly introduce the key properties of this well-known polymer, the difference between energetic and non-energetic binders in propellant and explosive formulations, the fundamentals for producing GAP and its copolymers, as well as for curing GAP using different types of curing agents. We use recent works as examples to illustrate the general approaches to curing GAP and its derivatives, while indicating a number of recently investigated curing agents. Next, we demonstrate that the properties of GAP can be modified either through internal (structural) alterations or through the introduction of external (plasticizers) additives and provide a summary of recent progress in this area, tying it in with studies on the properties of such modifications of GAP. Further on, we discuss relevant works dedicated to the applications of GAP as a binder for propellants and plastic-bonded explosives. Lastly, we indicate other, emerging applications of GAP and provide a summary of its mechanical and energetic properties.

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Section: Other Applications and Modifications Of Gapmentioning

confidence: 89%

Glycidyl Azide Polymer and its Derivatives-Versatile Binders for Explosives and Pyrotechnics: Tutorial Review of Recent Progress

Jarosz

Stolarczyk

Wawrzkiewicz-Jałowiecka

et al. 2019

Molecules

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“…Here, the terminal group of the foldamer is changed from the methoxy group to the azide group for the chemical cross-link reaction. The ion gels were prepared via copper-free azide–alkyne cycloaddition (AAC) reaction − between the azide-functionalized foldamer and the tetra-alkyne-ester cross-linker in an ionic liquid (Figure ). Due to the negligible vapor pressure of the ionic liquid, a gel film with a well-defined polymer concentration and thickness was obtained under vacuum conditions, which enabled mechanical characterization and actuation force measurements using a tensile testing machine.…”

Section: Introductionmentioning

confidence: 99%

Organogel Actuators Based on Redox-Responsive Foldamers: Amplification of Molecular Machine’s Motion to Macroscopic Scale

Ikeda

2022

ACS Appl. Polym. Mater.

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The amplification of nanoscale motions of artificial molecular machines to the macroscopic level is a major challenge. In this study, a redoxresponsive donor−acceptor (DA)-type foldamer, in which tetrathiafulvalene and viologen units are alternatively connected, was installed in an organogel network as a "working unit" to induce actuation. The ion gels were successfully synthesized via thermal azide−alkyne cycloaddition reaction between the azide-functionalized foldamer and the tetra-alkyne-ester crosslinker in an ionic liquid. The reaction efficiency of the cross-link was estimated from the stress−elongation curve. It was confirmed that the foldamers retained their electrochemical activity in the gel. Redox-responsive actuation of the gel was confirmed in a 0.1 M tetrabutylammonium•PF 6 acetonitrile solution. Through chemical oxidation, the characteristic length of the gel could be increased up to 125% of its initial length, indicating that the volume of the gel could be increased to 195%. Reversible gel size changes in response to the redox reactions were confirmed. The change in the gel size was induced by equilibrium shift of the foldamer conformation between the folded state and extended state. The actuation force during the reduction of the partially oxidized gel was ca. 3.4 kPa, indicating that the gel can generate 35 gf cm −2 . This actuation force proves the great potential of the redox-responsive foldamers to act as a molecular machine for realizing macroscopic actuation.

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Copper‐Free Synthesis of Cationic Glycidyl Triazolyl Polymers

Ikeda

2024

Macromol. Rapid Commun.

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Copper‐free synthesis of cationic glycidyl triazolyl polymers (GTPs) is achieved through a thermal azide‐alkyne cycloaddition reaction between glycidyl azide polymer and propiolic acid, followed by decarboxylation and quaternization of the triazole unit. For synthesizing nonfunctionalized GTP (GTP‐H), a microwave‐assisted method enhances the decarboxylation reaction of carboxy‐functionalized GTP (GTP‐COOH). Three variants of cationic GTPs with different N‐substituents [N‐ethyl, N‐butyl, and N‐tri(ethylene glycol) monomethyl ether (EG3)] are synthesized. The molecular weight of GTP‐H is determined via size exclusion chromatography. Thermal properties of all GTPs are characterized using differential scanning calorimetry and thermogravimetric analysis. The ionic conductivities of these cationic GTPs are assessed by impedance measurements. The conducting ion concentration and mobility are calculated based on the electrode polarization model. Among three cationic GTPs, the GTP with the N‐EG3 substituent exhibits the highest ionic conductivity, reaching 6.8 × 10−6 S cm−1 at 25 °C under dry conditions. When compared to previously reported reference polymers, the reduction of steric crowding around the triazolium unit is considered to be a key factor in enhancing ionic conductivity.

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Copper‐Free Synthesis of Glycidyl Triazolyl Polymers

Cited by 5 publications

References 35 publications

Glycidyl Azide Polymer and its Derivatives-Versatile Binders for Explosives and Pyrotechnics: Tutorial Review of Recent Progress

Glycidyl Azide Polymer and its Derivatives-Versatile Binders for Explosives and Pyrotechnics: Tutorial Review of Recent Progress

Organogel Actuators Based on Redox-Responsive Foldamers: Amplification of Molecular Machine’s Motion to Macroscopic Scale

Copper‐Free Synthesis of Cationic Glycidyl Triazolyl Polymers

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