Thiol–isocyanate “click” reactions: rapid development of functional polymeric surfaces

Hensarling, Ryan M.; Rahane, Santosh B.; LeBlanc, Arthur P.; Sparks, Bradley J.; White, Evan M.; Locklin, Jason; Patton, Derek L.

doi:10.1039/c0py00292e

Cited by 96 publications

(58 citation statements)

References 29 publications

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“…A thiourethane compound containing three furan moieties (TUF 3 ) was prepared in a convenient manner through the "click" thiol-isocyanate reaction 41,42 between a commercial hexamethylene diisocyanate isocyanurate trimer and 2-furfurylthiol. † Scheme 1 shows the chemical structure and synthesis scheme of these networks.…”

Section: Resultsmentioning

confidence: 99%

Healable shape memory (thio)urethane thermosets

et al. 2015

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Urethane-thiourethane networks combining shape memory properties and the ability to self-heal under mild temperature conditions via Diels-Alder (DA) chemistry were developed. As a result of the shape recovery effect, no external force was needed to bring the fracture surfaces into intimate contact during the healing process. Four network architectures with DA net-points were evaluated. Two systems were composed of either bismaleimidic or bisfuranic semi-crystallized polycaprolactone chains acting as shape memory switching segments (T trans = T m ), whereas the other two networks consisted of bis-/trismaleimidic and trisfuranic monomers and displayed glass transitions for initiating shape recovery behaviour (T trans = T g ). The formation of the DA cross-links, the DA reversibility and shape memory assisted scratch healing of the materials were studied by FTIR and 1 H-NMR spectrometry, differential scanning calorimetry, optical microscopy and tensile measurements. The results indicated that the healing efficiency of scratches depends strongly on the shape recovery ability, without which crack closure and thus the healing reaction could not occur. Two materials were found to feature good shape memory properties as well as efficient scratch-healing capacities, showing mechanical recoveries of 70-80% and the almost complete disappearance of scratches after healing at a mild temperature of 60°C for 1-3 days. These materials could find applications in diverse fields such as self-healing coatings.Scheme 1 Chemical structures of the (thio)urethane multi-maleimide and multi-furan monomers and schematic depiction of the SM networks reversibly cross-linked by the DA reaction. Polymer Chemistry PaperThis journal is

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Section: Resultsmentioning

confidence: 99%

Healable shape memory (thio)urethane thermosets

et al. 2015

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“…[77][78][79][80][81][82] Many of these reactions are accurately classified as click reactions and include examples from the thiol-ene (including the thiol-Michael variant), [77,[83][84][85][86][87][88][89][90][91][92][93] thiolyne, [78,85,[92][93][94][95][96][97][98] thiol-isocyanate, [99,100] thiol-halo, [101][102][103] and thiol-oxirane reactions, [104] Figure 4. Of these the radical-mediated thiol-ene reaction is currently the most widely employed in polymer synthesis and modification.…”

Section: Raft and Thiol-based Reactionsmentioning

confidence: 99%

Combining RAFT Radical Polymerization and Click/Highly Efficient Coupling Chemistries: A Powerful Strategy for the Preparation of Novel Materials

Harvison

Lowe

2011

Macromol. Rapid Commun.

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“…[109][110][111][112][113][114][115] The increasing number of routes available to transform the thiocarbonylthio end-group to a thiol provides an avenue to explore and exploit chemistry on the thiol functional 'handle'. Examples of reactions that can be performed at the terminal thiol group in RAFT-prepared (co)polymers include thiol-ene, [72][73][74]109,[116][117][118][119][120][121][122] thiolyne, [72,110,118,[123][124][125][126][127][128] thiol-isocyanate, [129,130] thiol-halo [77] and thiol-oxirane [67] reactions, many of which possess the key characteristics of click reactions. The thiol-ene reaction has been known for over 100 years [131] and is simply the hydrothiolation of a C¼C bond.…”

Section: Thermal Eliminationsmentioning

confidence: 99%