Thiol-ene “click” reactions and recent applications in polymer and materials synthesis

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The growing applications of click chemistry

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Living Radical Polymerization by the RAFT Process

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Living Radical Polymerization by the RAFT Process – A Third Update

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‘Click’ Chemistry in Polymer and Materials Science

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Thiol–enes: Chemistry of the past with promise for the future

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Michael addition reactions in macromolecular design for emerging technologies

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Click Chemistry beyond Metal‐Catalyzed Cycloaddition

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Living Radical Polymerization by the RAFT Process—A First Update

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Advances in RAFT polymerization: the synthesis of polymers with defined end-groups

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Robust, Efficient, and Orthogonal Synthesis of Dendrimers via Thiol-ene “Click” Chemistry

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Clicking polymers: a straightforward approach to novel macromolecular architectures

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‘Click’ Chemistry in Polymer and Material Science: An Update

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Reversible addition–fragmentation chain transfer (RAFT) radical polymerization and the synthesis of water-soluble (co)polymers under homogeneous conditions in organic and aqueous media

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The Emergence of Thiol–Ene Coupling as a Click Process for Materials and Bioorganic Chemistry

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“Click”‐Chemistry in Polymer and Material Science: the Update

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Thiol-yne click chemistry: A powerful and versatile methodology for materials synthesis

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Development of Thermal and Photochemical Strategies for Thiol−Ene Click Polymer Functionalization

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Mechanism and kinetics of dithiobenzoate‐mediated RAFT polymerization. I. The current situation

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Synthetic glycopolymers: an overview

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Thio-Click Modification of Poly[2-(3-butenyl)-2-oxazoline]

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RAFTing down under: Tales of missing radicals, fancy architectures, and mysterious holes

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Thiol−Yne Photopolymerizations: Novel Mechanism, Kinetics, and Step-Growth Formation of Highly Cross-Linked Networks

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Design and Synthesis of N -Maleimido-Functionalized Hydrophilic Polymers via Copper-Mediated Living Radical Polymerization: A Suitable Alternative to PEGylation Chemistry

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Beiträge zur Kenntniss der ungesättigten Verbindungen. II. Ueber die Addition von Mercaptanen an ungesättigte Kohlenwasserstoffe

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Problems and Possibilities of the Free‐Radical Addition of Thiols to Unsaturated Compounds

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Facile Preparation of Transition Metal Nanoparticles Stabilized by Well-Defined (Co)polymers Synthesized via Aqueous Reversible Addition-Fragmentation Chain Transfer Polymerization

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Thiol−Ene Photopolymerization Mechanism and Rate Limiting Step Changes for Various Vinyl Functional Group Chemistries

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The Rise of Azide–Alkyne 1,3-Dipolar ‘Click’ Cycloaddition and its Application to Polymer Science and Surface Modification

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Sequential Phosphine-Catalyzed, Nucleophilic Thiol−Ene/Radical-Mediated Thiol−Yne Reactions and the Facile Orthogonal Synthesis of Polyfunctional Materials

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Phosphine-Catalyzed Hydration and Hydroalkoxylation of Activated Olefins: Use of a Strong Nucleophile to Generate a Strong Base

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Thiol/ene photocurable polymers

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Convergent synthesis of 3-arm star polymers from RAFT-prepared poly(N,N-diethylacrylamide) via a thiol–ene click reaction

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Thiol−Ene Modification of 1,2-Polybutadiene Using UV Light or Sunlight

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Modification of RAFT‐polymers via thiol‐ene reactions: A general route to functional polymers and new architectures

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Clicking Pentafluorostyrene Copolymers: Synthesis, Nanoprecipitation, and Glycosylation

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Synthesis of dendrimers through divergent iterative thio‐bromo “Click” chemistry

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End group transformations of RAFT‐generated polymers with bismaleimides: Functional telechelics and modular block copolymers

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Synthesis of dendritic macromolecules through divergent iterative thio‐bromo “Click” chemistry and SET‐LRP

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Sequential thiol‐ene/thiol‐ene and thiol‐ene/thiol‐yne reactions as a route to well‐defined mono and bis end‐functionalized poly(N‐isopropylacrylamide)

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Evaluation and control of thiol–ene/thiol–epoxy hybrid networks

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Fluorescent Labeling of RAFT-Generated Poly(N-isopropylacrylamide) via a Facile Maleimide−Thiol Coupling Reaction

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Facile and Efficient One‐Pot Transformation of RAFT Polymer End Groups via a Mild Aminolysis/Michael Addition Sequence

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Highly Versatile and Robust Materials for Soft Imprint Lithography Based on Thiol‐ene Click Chemistry

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Photochemical Surface Patterning by the Thiol‐Ene Reaction

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Metal free thiol–maleimide ‘Click’ reaction as a mild functionalisation strategy for degradable polymers

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Surface Modification of Poly(divinylbenzene) Microspheres via Thiol−Ene Chemistry and Alkyne−Azide Click Reactions

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Modification of Gold Surfaces with Water-Soluble (Co)polymers Prepared via Aqueous Reversible Addition−Fragmentation Chain Transfer (RAFT) Polymerization

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Thiol-Selective Fluorogenic Probes for Labeling and Release

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Thermo-responsive polyoxazolines with widely tuneable LCST

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Direct, Controlled Synthesis of the Nonimmunogenic, Hydrophilic Polymer, Poly(N-(2-hydroxypropyl)methacrylamide) via RAFT in Aqueous Media

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Synthesis of thiol-linked neoglycopolymers and thermo-responsive glycomicelles as potential drug carrier

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Click Chemistry: A Powerful Tool to Create Polymer‐Based Macromolecular Chimeras

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Aminolysis of Polymers with Thiocarbonylthio Termini Prepared by RAFT Polymerization: The Difference between Polystyrene and Polymethacrylates

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Segmented Polythiourethane Elastomers through Sequential Thiol−Ene and Thiol−Isocyanate Reactions

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Reversible addition fragmentation chain transfer (raft) and hetero-diels–alder chemistry as a convenient conjugation tool for access to complex macromolecular designs

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Ternary Thiol−Ene/Acrylate Photopolymers: Effect of Acrylate Structure on Mechanical Properties

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The Thiol−Isocyanate Click Reaction: Facile and Quantitative Access to ω-End-Functional Poly(N,N-diethylacrylamide) Synthesized by RAFT Radical Polymerization

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Reactivity and Reversibility in the Reaction of Thiyl Radicals with Olefins1

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Efficient Usage of Thiocarbonates for Both the Production and the Biofunctionalization of Polymers

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Thermolysis of RAFT-Synthesized Polymers. A Convenient Method for Trithiocarbonate Group Elimination

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Glycopolymers via catalytic chain transfer polymerisation (CCTP), Huisgens cycloaddition and thiol–ene double click reactions

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Toward a toolbox of functional block copolymers via free-radical addition of mercaptans

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One- pot synthesis and biofunctionalization of glycopolymers via RAFT polymerization and thiol–ene reactions

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Thermolysis of RAFT-Synthesized Poly(Methyl Methacrylate)

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The effect of thiol and ene structures on thiol–ene networks: Photopolymerization, physical, mechanical and optical properties

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Chemistry and technology of 2‐alkenyl azlactones

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Synthetic Vaccines of Tumor‐Associated Glycopeptide Antigens by Immune‐Compatible Thioether Linkage to Bovine Serum Albumin

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Photopolymerization of Thiol-Alkynes: Polysulfide Networks

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Synthesis of Polymer−Biohybrids: From Small to Giant Surfactants

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Preparation of Poly(ethylene glycol) Protected Nanoparticles with Variable Bioconjugate Ligand Density

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Phosphine-mediated one-pot thiol–ene “click” approach to polymer–protein conjugates

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Surface Modification of Gold Nanorods with Polymers Synthesized by Reversible Addition−Fragmentation Chain Transfer Polymerization

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Diels–Alder “Click” Chemistry in Designing Dendritic Macromolecules

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Stabilization and Functionalization of Polymer Multilayers and Capsules via Thiol−Ene Click Chemistry

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The origin of the inductive effect

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Free Radical Addition of Butanethiol to Vegetable Oil Double Bonds

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Photoinduced Thiol−Ene Coupling as a Click Ligation Tool for Thiodisaccharide Synthesis

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The nucleophilic, phosphine-catalyzed thiol–ene click reaction and convergent star synthesis with RAFT-prepared homopolymers

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Bioinspired Polymer Vesicles Based on Hydrophilically Modified Polybutadienes

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Thiourethane‐based thiol‐ene high Tg networks: Preparation, thermal, mechanical, and physical properties

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Thiol−Allyl Ether−Methacrylate Ternary Systems. Polymerization Mechanism

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Facile postpolymerization end‐modification of RAFT polymers

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Thiol−Ene Reaction for the Synthesis of Multifunctional Branched Organosilanes

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One-Pot Synthesis of α,ω-Chain End Functional, Stereoregular, Star-Shaped Poly(lactide)

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Application of Thiol−Ene Chemistry to the Preparation of Carbosilane−Thioether Dendrimers

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Orthogonal “Relay” Reactions for Designing Functionalized Soft Nanoparticles

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Newly UV-curable polyurethane coatings prepared by multifunctional thiol- and ene-terminated polyurethane aqueous dispersions mixtures: Preparation and characterization

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Ultrathin gradient films using thiol‐ene polymerizations

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Metal-Free “Click” Chemistry: Efficient Polymer Modification via 1,3-Dipolar Cycloaddition of Nitrile Oxides and Alkynes

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Photopolymerization of ternary thiol–ene/acrylate systems: Film and network properties

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Modular Synthesis of Functional Block Copolymers

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Straightforward Synthesis of Cysteine-Reactive Telechelic Polystyrene

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Physical and Mechanical Properties of Photopolymerized Thiol−Ene/Acrylates

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Ultrathin Patterned Polymer Films on Surfaces Using Thiol−Ene Polymerizations

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Visualizing the dynamics of viral replication in living cells via Tat peptide delivery of nuclease-resistant molecular beacons

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Development and characterization of degradable thiol-allyl ether photopolymers

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Study of the Michael addition of β-cyclodextrin–thiol complexes to conjugated alkenes in water

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A Simple Route to Multimodal Composite Nanoparticles

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A doubly responsive AB diblock copolymer: RAFT synthesis and aqueous solution properties of poly (N‐isopropylacrylamide‐block‐4‐vinylbenzoic acid)

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Polymer‐Bound Thiol Groups on Poly(2‐oxazoline)s

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Racemization-Free Synthesis of S-Alkylated Cysteines via Thiol-ene Reaction

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Thiol‐Ene Radical Addition of L ‐Cysteine Derivatives to Low Molecular Weight Polybutadiene

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Efficient access to multi‐arm star block copolymers by a combination of ATRP and RAFT‐HDA click chemistry

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A Study into the Stability of 3,6-Dihydro-2H-thiopyran Rings: Key Linkages in the RAFT Hetero-Diels−Alder Click Concept

Sinnwell, S., Synatschke, C. V., Junkers, T., Stenzel, M. H., & Barner‐Kowollik, C. (2008) · Macromolecules · doi:10.1021/ma8013959 · Cited by 55 · see citing works

Tailored polyester nanoparticles: post-modification with dendritic transporter and targeting units via reductive amination and thiol-ene chemistry

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Photopolymerization of thiol‐ene systems based on oligomeric thiols

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Gel Permeation Chromatography Characterization of the Chain Length Distributions in Thiol−Acrylate Photopolymer Networks

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Enthalpy Relaxation of Photopolymerized Thiol−Ene Networks: Structural Effects

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Synthesis of glyco‐microspheres via a thiol‐ene coupling reaction

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The isolation of a zwitterionic initiating species for ethyl cyanoacrylate (ECA) polymerization and the identification of the reaction products between 1°, 2°, and 3° amines with ECA

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Self‐Assembling Diblock Copolymers of Poly[N‐(2‐hydroxypropyl)methacrylamide] and a β‐Sheet Peptide

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Thermal reactions of thiyl radicals

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Synthesis, Structure, and Physicochemical Characteristics of Thiols

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The Effect of Structure on Mercaptan Dissociation Constants1

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Receptor site labeling through functional groups. 2. Reactivity of maleimide groups

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Effects of Monomer Functionality and Hydrogen Bonding on the Polymerization Kinetics and Properties of Thiol−Ene Networks

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A novel bifunctional maleimido CHX-A″ chelator for conjugation to thiol-containing biomolecules

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Facile and efficient synthesis of star-shaped oligomers from a triazine core

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Conjugation of ATIII‐Binding Pentasaccharides to Extend the Half‐Life of Proteins: Long‐Acting Insulin

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A Sensitive Assay for Maleimide Groups

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Untitled work

Kolb (2001) · doi:10.1002/1521-3773(20010601)40:11

Thiol-click chemistry: a multifaceted toolbox for small molecule and polymer synthesis

Hoyle, C. E., Lowe, A. B., & Bowman, C. N. (2010) · Chemical Society Reviews · doi:10.1039/b901979k · Cited by 1,639 · see citing works

Designing degradable hydrogels for orthogonal control of cell microenvironments

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Controlled Polymerization of Next-Generation Renewable Monomers and Beyond

Yao, K., & Tang, C. (2013) · Macromolecules · doi:10.1021/ma3019574 · Cited by 485 · see citing works

Complex polymer architectures via RAFT polymerization: from fundamental process to extending the scope using click chemistry and nature's building blocks

Gregory, A., & Stenzel, M. H. (2012) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2011.08.004 · Cited by 470 · see citing works

Towards organoid culture without Matrigel

Kozlowski, M. T., Crook, C. J., & Ku, H. T. (2021) · Communications Biology · doi:10.1038/s42003-021-02910-8 · Cited by 409 · see citing works

Linear/Network Poly(ε-caprolactone) Blends Exhibiting Shape Memory Assisted Self-Healing (SMASH)

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Two‐Stage Reactive Polymer Network Forming Systems

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A Route to Aliphatic Poly(ester)s with Thiol Pendant Groups: From Monomer Design to Editable Porous Scaffolds

Fuoco, T., Finne-Wistrand, A., & Pappalardo, D. (2016) · Biomacromolecules · doi:10.1021/acs.biomac.6b00005 · Cited by 46 · see citing works

Assessments of antibacterial and physico-mechanical properties for dental materials with chemically anchored quaternary ammonium moieties: thiol-ene-methacrylate vs. conventional methacrylate system

Beigi Burujeny, S., Atai, M., & Yeganeh, H. (2015) · Dental Materials · doi:10.1016/j.dental.2014.12.014 · Cited by 32 · see citing works

Cytosolic Uptake of Large Monofunctionalized Dextrans

Chyan, W., Kilgore, H. R., & Raines, R. T. (2018) · Bioconjugate Chemistry · doi:10.1021/acs.bioconjchem.8b00198 · Cited by 20 · see citing works

Thiol–Ene Chemistry

Cramer, N. B., & Bowman, C. N. (2017) · doi:10.1002/9783527683451.ch5 · Cited by 15 · see citing works

Largely improved electromechanical properties of thermoplastic dielectric elastomers by grafting carboxyl onto SBS through thiol–ene click chemistry

Tian, M., Yan, H., Sun, H., et al. (2016) · RSC Advances · doi:10.1039/c6ra17871e · Cited by 32 · see citing works

Synthesis and characterization of silicon-containing hyperbranched polymers via thiol-ene click reaction

Xue, L., Yang, Z., Wang, D., et al. (2013) · Journal of Organometallic Chemistry · doi:10.1016/j.jorganchem.2013.01.024 · Cited by 26 · see citing works

Peptide Conjugation via CuAAC ‘Click’ Chemistry

Fuaad, A. A. H. A., Azmi, F., Skwarczyński, M., et al. (2013) · Molecules · doi:10.3390/molecules181113148 · Cited by 126 · see citing works

Conjugation of hemin to G-quadruplex forming oligonucleotide using click chemistry

Kosman, J., Stanislawska, A., Głuszyńska, A., et al. (2017) · International Journal of Biological Macromolecules · doi:10.1016/j.ijbiomac.2017.03.170 · Cited by 15 · see citing works