Thiol‐yne photoclick polymerization as a method for preparing <scp>imidazolium‐containing</scp> ionene networks

Lindenmeyer, Katelyn M.; Miller, Kevin M.

doi:10.1002/pol.20210629

Cited by 3 publications

(4 citation statements)

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“…This aspect was explored by Lindenmeyer and Miller (Section 2.6.1). 93 Hirai et al 94 developed the clickable monomer 15 in order to form a PIL with high ionic conductivity. The azide and alkyne groups thermally condense to form racemic mixtures of 1,2,3-triazole linking groups when heated to about 120 °C.…”

Section: Vinyl Monomersmentioning

confidence: 99%

“…97 Similarly, Lindenmeyer and Miller developed the 1,3-bis(hexynyl) imidazolium TFSI, 26, to make an interesting ionene and highly cross-linked ionogels with PTMP. 93 Other click chemistries of note include water-isocyanate (and water isothiocyanate) addition, amine-isocyanate (urea) and amine-isothiocyanate (thiourea) coupling, amine-glycidyl ether (oxirane) coupling, hydroxy-isocyanate (urethane) coupling and hydroxy-isothiocyanate coupling, Diels−Alder coupling, and aldehyde-alkoxyamine coupling (oxime ligation.). Most of these chemistries have yet to be applied to PIL systems, though some have proven useful in making new materials with CILs (Section 4.4.2).…”

Section: Vinyl Monomersmentioning

confidence: 99%

“…Lindenmeyer and Miller created 93 similar ionene networks except that they used hexynyl chloride instead of hexenyl chloride when forming the 1,3-bishexynyl imidazolium moiety. They anion exchanged TFSI for chloride.…”

Section: Cross-linkingmentioning

confidence: 99%

“…Bontrager and co-workers developed 1,3-bis(hexeny)imidazolium X – , 25 , to make cross-linked ionene ionogels using thiol–ene click chemistry with PTMP, pentaerythritol tetrakis(3-mercaptoproprionate) (Section ). Similarly, Lindenmeyer and Miller developed the 1,3-bis(hexynyl) imidazolium TFSI, 26 , to make an interesting ionene and highly cross-linked ionogels with PTMP …”

Section: Synthesesmentioning

confidence: 99%

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Polymerized and Colloidal Ionic Liquids─Syntheses and Applications

Li,

Yan,

Texter

2024

Chem. Rev.

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The breadth and importance of polymerized ionic liquids (PILs) are steadily expanding, and this review updates advances and trends in syntheses, properties, and applications over the past five to six years. We begin with an historical overview of the genesis and growth of the PIL field as a subset of materials science. The genesis of ionic liquids (ILs) over nano to meso lengthscales exhibiting 0D, 1D, 2D, and 3D topologies defines colloidal ionic liquids, CILs, which compose a subclass of PILs and provide a synthetic bridge between IL monomers (ILMs) and micro to macroscale PIL materials. The second focus of this review addresses design and syntheses of ILMs and their polymerization reactions to yield PILs and PIL-based materials. A burgeoning diversity of ILMs reflects increasing use of nonimidazolium nuclei and an expanding use of step-growth chemistries in synthesizing PIL materials. Radical chain polymerization remains a primary method of making PILs and reflects an increasing use of controlled polymerization methods.Step-growth chemistries used in creating some CILs utilize extensive cross-linking. This cross-linking is enabled by incorporating reactive functionalities in CILs and PILs, and some of these CILs and PILs may be viewed as exotic cross-linking agents. The third part of this update focuses upon some advances in key properties, including molecular weight, thermal properties, rheology, ion transport, self-healing, and stimuli-responsiveness. Glass transitions, critical solution temperatures, and liquidity are key thermal properties that tie to PIL rheology and viscoelasticity. These properties in turn modulate mechanical properties and ion transport, which are foundational in increasing applications of PILs. Cross-linking in gelation and ionogels and reversible step-growth chemistries are essential for self-healing PILs. Stimuli-responsiveness distinguishes PILs from many other classes of polymers, and it emphasizes the importance of segmentally controlling and tuning solvation in CILs and PILs. The fourth part of this review addresses development of applications, and the diverse scope of such applications supports the increasing importance of PILs in materials science. Adhesion applications are supported by ionogel properties, especially crosslinking and solvation tunable interactions with adjacent phases. Antimicrobial and antifouling applications are consequences of the cationic nature of PILs. Similarly, emulsion and dispersion applications rely on tunable solvation of functional groups and on how such groups interact with continuous phases and substrates. Catalysis is another significant application, and this is an historical tie between ILs and PILs. This component also provides a connection to diverse and porous carbon phases templated by PILs that are catalysts or serve as supports for catalysts. Devices, including sensors and actuators, also rely on solvation tuning and stimuliresponsiveness that include photo and electrochemical stimuli. We conclude our view of applications with 3D printi...

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Section: Vinyl Monomersmentioning

confidence: 99%

Section: Vinyl Monomersmentioning

confidence: 99%

Section: Cross-linkingmentioning

confidence: 99%

Section: Synthesesmentioning

confidence: 99%

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Polymerized and Colloidal Ionic Liquids─Syntheses and Applications

Li,

Yan,

Texter

2024

Chem. Rev.

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Efficient and eco-friendly UV-cured polyurethane coating: Harnessing thiol-yne systems for corrosion protection

Najafi-Shoa,

Barikani,

Ehsani

et al. 2024

Materials Today Communications

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Thiol–Ene/Yne Click Chemistry in Polymer Science

Ghosh,

Bag,

2024

Click Chemistry in Polymer Science

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In this chapter, we have discussed the history of the resurgence of thiol–ene/yne click chemistry in polymer science along with their mechanistic pathways under radical conditions either thermally or photochemically initiated. The recent instances of the utilization of the thiol–ene/yne click reaction for synthesis of polymeric networks, linear and hyperbranched polymers, and dendrimers are highlighted. Stereo-selective polymer synthesis via thiol–yne click polymerization is an important recent development that has also been discussed thoroughly. For the synthesis aspect, a catalyst-free greener approach is given priority along with the utilization of renewable resources, which is also a future direction for the synthesis of sustainable and environment-friendly polymer design. We anticipate that this contribution will provide a foundation to sketch the next-generation polymeric materials via thiol–ene/yne click chemistry for various applications, such as drug-delivery vehicles, biomaterials, high refractive index optical materials, photovoltaic materials, adhesives and coatings.

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Thiol‐yne photoclick polymerization as a method for preparing imidazolium‐containing ionene networks

Cited by 3 publications

References 46 publications

Polymerized and Colloidal Ionic Liquids─Syntheses and Applications

Polymerized and Colloidal Ionic Liquids─Syntheses and Applications

Efficient and eco-friendly UV-cured polyurethane coating: Harnessing thiol-yne systems for corrosion protection

Thiol–Ene/Yne Click Chemistry in Polymer Science

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