Thiol‐Bromo Click Reaction for One‐Pot Synthesis of Star‐Shaped Polymers

Beyer, Valentin P.; Cattoz, Beatrice; Becer, C. Remzi

doi:10.1002/marc.202000519

Cited by 3 publications

(3 citation statements)

References 30 publications

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“…Specifically, the thiol group on BDB could undergo the thiol-bromo "click" reaction with the terminal bromine on the side chains of the bottlebrush polymers, leading to the formation of the dynamic crosslinking point. 55 Thanks to the well-designed architecture, we successfully synthesized the dynamically cross-linked bottlebrush polymer supersoft material, referred to as Brush-DM. Additionally, the nondynamically cross-linked bottlebrush polymer material, cross-linked using the traditional dithiol molecule, was named Brush-NM (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“… , Additionally, the chemical structure of the BDB was further substantiated by its 1 H NMR spectrum (Figure S2). Specifically, the thiol group on BDB could undergo the thiol-bromo “click” reaction with the terminal bromine on the side chains of the bottlebrush polymers, leading to the formation of the dynamic cross-linking point . Thanks to the well-designed architecture, we successfully synthesized the dynamically cross-linked bottlebrush polymer supersoft material, referred to as Brush-DM.…”

Section: Resultsmentioning

confidence: 99%

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Self-Healing and Adhesive Supersoft Materials Derived from Dynamically Cross-Linked Bottlebrush Polymers for Flexible Sensors

Du,

Li,

et al. 2024

Macromolecules

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Multifunctional bottlebrush polymer supersoft materials are highly desirable for the development of nextgeneration flexible electronic devices. Herein, we report a facile strategy for the fabrication of bottlebrush polymer supersoft materials integrated with self-healing and adhesive functionalities. These are achieved by the first fabrication of the bottlebrush poly(n-butyl acrylate) (PnBA) via combining atom transfer radical polymerization with ring-opening metathesis polymerization and subsequent formation of dynamically cross-linked networks via "click" thiol-bromo reaction between Br end groups of PnBA side chains and dithiol-containing boronic ester cross-linker. Owing to the unique architecture and the reversible boron ester bonds, the unique bottlebrush architecture and fast bond-reforming kinetics of boron ester bonds impart the resultant materials with supersoftness with a shear modulus as low as 5 kPa and high self-healing efficiency over 90%. Moreover, owing to the extremely low glass transition temperature of PnBA segments, they also display strong adhesiveness to many substrates. The as-prepared strain sensors show an excellent ability to detect a large range of strains from an ultralow strain of 0.1% to a large strain of 100%. This work has provided a facile and promising approach to the development of multifunctional supersoft materials, which hold great potential as functional sensors for flexible electronics.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Self-Healing and Adhesive Supersoft Materials Derived from Dynamically Cross-Linked Bottlebrush Polymers for Flexible Sensors

Du,

Li,

et al. 2024

Macromolecules

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“…Thiol-based reactions are the most popular click chemistry methodology applied to rubbers and comprise a family of reactions like the thiol-ene, [96] thiol-yne, [119,120] thiol-halogen, [121] thiol-epoxy, [122][123][124][125] thiol-isocyanate, [126] which are often described as thiol-X reactions. Thiol additions can also proceed through Michael additions in the presence of catalyst.…”

Section: Rubber Modifications Via Thiol-x Reactionsmentioning

confidence: 99%

Enzymatic and Chemical Approaches for Post‐Polymerization Modifications of Diene Rubbers: Current state and Perspectives

Soares

Steinbüchel

2021

Macromolecular Bioscience

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Diene rubbers are polymeric materials which present elastic properties and have double bonds in the macromolecular backbone after the polymerization process. Post-polymerization modifications of rubbers can be conducted by enzymatic or chemical methods. Enzymes are environmentally friendly catalysts and with the increasing demand for rubber waste management, biodegradation and biomodifications have become hot topics of research. Some rubbers are renewable materials and are a source of organic molecules, and biodegradation can be conducted to obtain either oligomers or monomers. On the other hand, chemical modifications of rubbers by click-chemistry are important strategies for the creation and combination of new materials. In a way to expand the scope of uses to other non-traditional applications, several and effective modifications can be conducted with diene rubbers. Two groups of efficient tools, enzymatic, and chemical modifications in diene rubbers, are summarized in this review. By analyzing stereochemical and reactivity aspects, the authors also point to some applications perspectives for biodegradation products and to rational modifications of diene rubbers by combining both methodologies.

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Click Chemistry for Block, Graft, and Star Copolymers

Tunca

2024

Click Chemistry in Polymer Science

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In this book chapter, various types of click and orthogonal multiple click, and multicomponent reactions (MCRs), alone or in combination, are presented for the design and preparation of complex macromolecular structures with diverse topologies (block, graft, and star-shaped), some of which had been never achieved before. These reactions enable straightforward coupling of various reactive building blocks, often by different polymerization methods, to produce macromolecular architectures, such as block, graft, and star polymers, through one-pot or sequential reaction techniques. The relevant publications are listed in tables according to the date of their appearance in the literature, from oldest to newest.

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Thiol‐Bromo Click Reaction for One‐Pot Synthesis of Star‐Shaped Polymers

Cited by 3 publications

References 30 publications

Self-Healing and Adhesive Supersoft Materials Derived from Dynamically Cross-Linked Bottlebrush Polymers for Flexible Sensors

Self-Healing and Adhesive Supersoft Materials Derived from Dynamically Cross-Linked Bottlebrush Polymers for Flexible Sensors

Enzymatic and Chemical Approaches for Post‐Polymerization Modifications of Diene Rubbers: Current state and Perspectives

Click Chemistry for Block, Graft, and Star Copolymers

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