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A Model for Late-Stage Modification of Polyurethane Dendrimers Using Thiol-Ene Click Chemistry.

ABSTRACT: Dendritic materials possessing urethane linkage are surprisingly more stable than similar structures having functional groups such as ether, ester, amide, or carbosilane. This generates profound interest in dendritic polyurethanes. Construction of a well-defined polyurethane dendrimer is, however, challenging because of isocyanates' high reactivity. As a model of our ongoing dendrimer-research, herein, we report a protecting group-free one-pot multicomponent Curtius reaction to furnish a robust and versatile AB₂-type dendron, which ensures late-stage modification of both the dendron and dendritic macromolecule yielding a surface functionalized polyurethane dendrimer. While 5-hydroxyisophthalic acid, 11-bromoundecanol, and 4-penten-1-ol were utilized in the construction of the dendron, thiol-ene click chemistry was employed for the late-stage modification. Novel dendrons and dendrimers synthesized were characterized by NMR (1D and 2D) and high-resolution MALDI-TOF analysis. This strategy allows an easy late-stage modification of dendritic macromolecules and is highly useful in the synthesis of both symmetrical and unsymmetrical dendrimers (Janus dendrimers).

SUBMITTER: Poudel DP

PROVIDER: S-EPMC8154125 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Functional graphene by thiol-ene click chemistry.

Project description:Thiol-ene click reaction was successfully employed for chemical modification of graphene oxide (GO) by one-step synthesis. Herein, 2,2-azobis(2-methylpropionitrile) (AIBN) was used as thermal catalyst and cysteamine hydrochloride (HS-(CH2 )2 -NH2 HCl) was used as thiol-containing compound, which is incorporated to GO surface upon reaction with the C=C bonds. The hydrochloride acts as protecting group for the amine, which is finally eliminated by adding sodium hydroxide. The modified GO contains both S- and N-containing groups (NS-GO). We found that NS-GO sheets form good dispersion in water, ethanol, and ethylene glycol. These graphene dispersions can be processed into functionalized graphene film. Besides, it was demonstrated that NS-GO was proved to be an excellent host matrix for platinum nanoparticles. The developed method paves a new way for graphene modification and its functional nanocomposites.

| S-EPMC6174942 | biostudies-literature

On-resin peptide macrocyclization using thiol-ene click chemistry.

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Modification of Polyurethane Sponge Based on the Thiol-Ene Click Reaction and Its Application for Oil/Water Separation.

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Chemical modification of <i>Bombyx mori</i> silk fibers with vinyl groups for thiol-ene click chemistry.

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Highly Water Dispersible Functionalized Graphene by Thermal Thiol-Ene Click Chemistry.

Project description:Functionalization of pristine graphene to achieve high water dispersibility remains as a key obstacle owing to the high hydrophobicity and absence of reactive functional groups on the graphene surface. Herein, a green and simple modification approach to prepare highly dispersible functionalized graphene via thermal thiol-ene click reaction was successfully demonstrated on pristine graphene. Specific chemical functionalities (-COO, -NH2 and -S) on the thiol precursor (L-cysteine ethyl ester) were clicked directly on the sp2 carbon of graphene framework with grafting density of 1 unit L-cysteine per 113 carbon atoms on graphene. This functionalized graphene was confirmed with high atomic content of S (4.79 at % S) as well as the presence of C-S-C and N-H species on the L-cysteine functionalized graphene (FG-CYS). Raman spectroscopy evidently corroborated the modification of graphene to FG-CYS with an increased intensity ratio of D and G band, ID/IG ratio (0.3 to 0.7), full-width at half-maximum of G band, FWHM [G] (20.3 to 35.5) and FWHM [2D] (64.8 to 90.1). The use of ethanol as the reaction solvent instead of common organic solvents minimizes the chemical hazards exposure to humans and the environment. This direct attachment of multifunctional groups on the surface of pristine graphene is highly demanded for graphene ink formulations, coatings, adsorbents, sensors and supercapacitor applications.

| S-EPMC8198566 | biostudies-literature

SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization.

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Thiol-ene click chemistry: a biocompatible way for orthogonal bioconjugation of colloidal nanoparticles.

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| S-EPMC5628335 | biostudies-literature

Photogenerated lectin sensors produced by thiol-ene/yne photo-click chemistry in aqueous solution.

Project description:The photoinitiated radical reactions between thiols and alkenes/alkynes (thiol-ene and thiol-yne chemistry) have been applied to a functionalization methodology to produce carbohydrate-presenting surfaces for analyses of biomolecular interactions. Polymer-coated quartz surfaces were functionalized with alkenes or alkynes in a straightforward photochemical procedure utilizing perfluorophenylazide (PFPA) chemistry. The alkene/alkyne surfaces were subsequently allowed to react with carbohydrate thiols in water under UV-irradiation. The reaction can be carried out in a drop of water directly on the surface without photoinitiator, and any disulfide side products were easily washed away after the functionalization process. The resulting carbohydrate-presenting surfaces were evaluated in real-time studies of protein-carbohydrate interactions using a quartz crystal microbalance (QCM) flow-through system with recurring injections of selected lectins, with intermediate regeneration steps using low pH buffer. The resulting methodology proved fast, efficient and scalable to high-throughput analysis formats, and the produced surfaces showed significant protein binding with expected selectivities of the lectins used in the study.

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Assembly of PEG Microgels into Porous Cell-Instructive 3D Scaffolds via Thiol-Ene Click Chemistry.

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