‘Click’ Chemistry and Polymers

A special issue of Polymers (ISSN 2073-4360). This special issue belongs to the section "Polymer Chemistry".

Deadline for manuscript submissions: closed (31 December 2021) | Viewed by 22681

Special Issue Editors

Division of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore City, Singapore
Interests: corannulene polymers; “click” chemistry; ”click” polymerization; polycyclic aromatic hydrocarbons; polymeric fullerene hosts
Department of Chemical and Biological Engineering, Korea University, Seoul 02841, Korea
Interests: polymer synthesis; thermoresponsive polymers; “click” chemistry; azobenzene polymers

Special Issue Information

Dear Colleagues,

“Click” chemistry encompasses reactions that are high yielding, fast, modular, and wide in scope. They are practical and tolerant of a variety of functional groups. Finally, product isolation is expected to be effortless due to a lack of by-products. These features are ideal for polymer synthesis and functionalization purposes. Hence, the synergy between the two disciplines has given rise to an area of intense research activity. In this Special Issue we would like to showcase this growing area of research in which “click” chemistry is paving the way to new polymer synthesis methodologies and new polymeric functional materials. As Guest Editors, we invite contributions in the form of original research articles or reviews on this subject.

Prof. Dr. Mihaiela C. Stuparu
Prof. Dr. Anzar Khan
Guest Editors

Manuscript Submission Information

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Keywords

  • “click” chemistry
  • “click” polymerization
  • “click” hydrogels
  • polymer synthesis
  • polymer functionalization
  • post-polymerization modification
  • polymer brushes
  • surface functionalization
  • polymer nanoparticles
  • polymer networks
  • photopolymerization
  • surface patterning
  • micro and nano-fabrication
  • soft lithography
  • functional polymers

Published Papers (6 papers)

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Research

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7 pages, 6459 KiB  
Communication
Micellar Assembly and Disassembly of Organoselenium Block Copolymers through Alkylation and Dealkylation Processes
by Taejun Eom and Anzar Khan
Polymers 2021, 13(15), 2456; https://0-doi-org.brum.beds.ac.uk/10.3390/polym13152456 - 27 Jul 2021
Cited by 2 | Viewed by 1648
Abstract
The aim of this work is to demonstrate that the alkylation and dealkylation of selenium atoms is an effective tool in controlling polymer amphiphilicity and, hence, its assembly and disassembly process in water. To establish this concept, poly(ethylene glycol)-block-poly(glycidyl methacrylate) was prepared. A [...] Read more.
The aim of this work is to demonstrate that the alkylation and dealkylation of selenium atoms is an effective tool in controlling polymer amphiphilicity and, hence, its assembly and disassembly process in water. To establish this concept, poly(ethylene glycol)-block-poly(glycidyl methacrylate) was prepared. A post-synthesis modification with phenyl selenolate through a base-catalyzed selenium-epoxy ‘click’ reaction then gave rise to the side-chain selenium-containing block copolymer with an amphiphilic character. This polymer assembled into micellar structures in water. However, silver tetrafluoroborate-promoted alkylation of the selenium atoms resulted in the formation of hydrophilic selenonium tetrafluoroborate salts. This enhancement in the chemical polarity of the second polymer block removed the amphiphilic character from the polymer chain and led to the disassembly of the micellar structures. This process could be reversed by restoring the original amphiphilic polymer character through the dealkylation of the cations. Full article
(This article belongs to the Special Issue ‘Click’ Chemistry and Polymers)
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10 pages, 1798 KiB  
Article
Joint-Linker Type Ionic Gels Using Polymerizable Ionic Liquid as a Crosslinker via Thiol-Ene Click Reactions
by Kumkum Ahmed, Aoi Inagaki and Naofumi Naga
Polymers 2020, 12(12), 2844; https://0-doi-org.brum.beds.ac.uk/10.3390/polym12122844 - 29 Nov 2020
Cited by 2 | Viewed by 2117
Abstract
In this work, we report the synthesis of ion-conductive gels, or ionic gels, via thiol-ene click reactions. The novel gel systems consist of the multifunctional thiol monomers tris[(3-mercaptopropionyloxy)-ethyl]-isocyanurate (TEMPIC), pentaerythritol tetrakis(3-mercaptopropionate) (PEMP), and dipentaerythritol hexakis(3-mercaptopionate) (DPMP) as joint molecules and bifunctional allyl ionic [...] Read more.
In this work, we report the synthesis of ion-conductive gels, or ionic gels, via thiol-ene click reactions. The novel gel systems consist of the multifunctional thiol monomers tris[(3-mercaptopropionyloxy)-ethyl]-isocyanurate (TEMPIC), pentaerythritol tetrakis(3-mercaptopropionate) (PEMP), and dipentaerythritol hexakis(3-mercaptopionate) (DPMP) as joint molecules and bifunctional allyl ionic liquid (IL) as a crosslinker. The thiol-ene reaction was carried out in lithium bis(trifluoromethanesulfonyl)imide (Li-TFSI) in a propylene carbonate (PC) (1 M) solvent system via a photopolymerization process. The chemical structure and mechanical, thermal, and conductive properties of the gels were investigated using Fourier transform infrared (FTIR) spectroscopy, thermogravimetric analysis (TGA), compression tests, and impedance spectroscopy, respectively. The mechanical and conductive properties of the ionic gels were found to be largely dependent on the monomer content and functionalities of the joint molecules. TGA revealed good thermal stability of the gels up to 100 °C. An ionic conductivity of 4.89 mS cm−1 was realized at room temperature (298 K) for low-functional thiol monomers, and a further increase in ionic conductivity was observed with an increase in Li+ ion content and temperature. Full article
(This article belongs to the Special Issue ‘Click’ Chemistry and Polymers)
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13 pages, 3269 KiB  
Article
Multifunctional and Transformable ‘Clickable’ Hydrogel Coatings on Titanium Surfaces: From Protein Immobilization to Cellular Attachment
by Tugce Nihal Gevrek, Aysun Degirmenci, Rana Sanyal and Amitav Sanyal
Polymers 2020, 12(6), 1211; https://0-doi-org.brum.beds.ac.uk/10.3390/polym12061211 - 26 May 2020
Cited by 11 | Viewed by 3698
Abstract
Multifunctionalizable hydrogel coatings on titanium interfaces are useful in a wide range of biomedical applications utilizing titanium-based materials. In this study, furan-protected maleimide groups containing multi-clickable biocompatible hydrogel layers are fabricated on a titanium surface. Upon thermal treatment, the masked maleimide groups within [...] Read more.
Multifunctionalizable hydrogel coatings on titanium interfaces are useful in a wide range of biomedical applications utilizing titanium-based materials. In this study, furan-protected maleimide groups containing multi-clickable biocompatible hydrogel layers are fabricated on a titanium surface. Upon thermal treatment, the masked maleimide groups within the hydrogel are converted to thiol-reactive maleimide groups. The thiol-reactive maleimide group allows facile functionalization of these hydrogels through the thiol-maleimide nucleophilic addition and Diels–Alder cycloaddition reactions, under mild conditions. Additionally, the strained alkene unit in the furan-protected maleimide moiety undergoes radical thiol-ene reaction, as well as the inverse-electron-demand Diels–Alder reaction with tetrazine containing molecules. Taking advantage of photo-initiated thiol-ene ‘click’ reactions, we demonstrate spatially controlled immobilization of the fluorescent dye thiol-containing boron dipyrromethene (BODIPY-SH). Lastly, we establish that the extent of functionalization on hydrogels can be controlled by attachment of biotin-benzyl-tetrazine, followed by immobilization of TRITC-labelled ExtrAvidin. Being versatile and practical, we believe that the described multifunctional and transformable ‘clickable’ hydrogels on titanium-based substrates described here can find applications in areas involving modification of the interface with bioactive entities. Full article
(This article belongs to the Special Issue ‘Click’ Chemistry and Polymers)
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13 pages, 1448 KiB  
Article
Direct Conjugation of Streptavidin to Encoded Hydrogel Microparticles for Multiplex Biomolecule Detection with Rapid Probe-Set Modification
by Yoon Ho Roh, Ju Yeon Kim, Seok Joon Mun, Hye Sun Lee, Changhyun Hwang, Kyong Hwa Park and Ki Wan Bong
Polymers 2020, 12(3), 546; https://0-doi-org.brum.beds.ac.uk/10.3390/polym12030546 - 03 Mar 2020
Cited by 4 | Viewed by 4748
Abstract
Encoded hydrogel microparticles synthesized via flow lithography have drawn attention for multiplex biomarker detection due to their high multiplex capability and solution-like hybridization kinetics. However, the current methods for preparing particles cannot achieve a flexible, rapid probe-set modification, which is necessary for the [...] Read more.
Encoded hydrogel microparticles synthesized via flow lithography have drawn attention for multiplex biomarker detection due to their high multiplex capability and solution-like hybridization kinetics. However, the current methods for preparing particles cannot achieve a flexible, rapid probe-set modification, which is necessary for the production of various combinations of target panels in clinical diagnosis. In order to accomplish the unmet needs, streptavidin was incorporated into the encoded hydrogel microparticles to take advantage of the rapid streptavidin–biotin interactions that can be used in probe-set modification. However, the existing methods suffer from low efficiency of streptavidin conjugation, cause undesirable deformation of particles, and impair the assay capability. Here, we present a simple and powerful method to conjugate streptavidin to the encoded hydrogel microparticles for better assay performance and rapid probe-set modification. Streptavidin was directly conjugated to the encoded hydrogel microparticles using the aza-Michael addition click reaction, which can proceed in mild, aqueous condition without catalysts. A highly flexible and sensitive assay was developed to quantify DNA and proteins using streptavidin-conjugated encoded hydrogel microparticles. We also validated the potential applications of our particles conducting multiplex detection of cancer-related miRNAs. Full article
(This article belongs to the Special Issue ‘Click’ Chemistry and Polymers)
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Review

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19 pages, 4397 KiB  
Review
Click Chemistry Enabling Covalent and Non-Covalent Modifications of Graphene with (Poly)saccharides
by Hu Li and Raffaello Papadakis
Polymers 2021, 13(1), 142; https://0-doi-org.brum.beds.ac.uk/10.3390/polym13010142 - 31 Dec 2020
Cited by 13 | Viewed by 4743
Abstract
Graphene is a material with outstanding properties and numerous potential applications in a wide range of research and technology areas, spanning from electronics, energy materials, sensors, and actuators to life-science and many more. However, the insolubility and poor dispersibility of graphene are two [...] Read more.
Graphene is a material with outstanding properties and numerous potential applications in a wide range of research and technology areas, spanning from electronics, energy materials, sensors, and actuators to life-science and many more. However, the insolubility and poor dispersibility of graphene are two major problems hampering its use in certain applications. Tethering mono-, di-, or even poly-saccharides on graphene through click-chemistry is gaining more and more attention as a key modification approach leading to new graphene-based materials (GBM) with improved hydrophilicity and substantial dispersibility in polar solvents, e.g., water. The attachment of (poly)saccharides on graphene further renders the final GBMs biocompatible and could open new routes to novel biomedical and environmental applications. In this review, recent modifications of graphene and other carbon rich materials (CRMs) through click chemistry are reviewed. Full article
(This article belongs to the Special Issue ‘Click’ Chemistry and Polymers)
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44 pages, 6127 KiB  
Review
The Use of Click-Type Reactions in the Preparation of Thermosets
by Osman Konuray, Xavier Fernández-Francos, Silvia De la Flor, Xavier Ramis and Àngels Serra
Polymers 2020, 12(5), 1084; https://0-doi-org.brum.beds.ac.uk/10.3390/polym12051084 - 09 May 2020
Cited by 23 | Viewed by 4814
Abstract
Click chemistry has emerged as an effective polymerization method to obtain thermosets with enhanced properties for advanced applications. In this article, commonly used click reactions have been reviewed, highlighting their advantages in obtaining homogeneous polymer networks. The basic concepts necessary to understand network [...] Read more.
Click chemistry has emerged as an effective polymerization method to obtain thermosets with enhanced properties for advanced applications. In this article, commonly used click reactions have been reviewed, highlighting their advantages in obtaining homogeneous polymer networks. The basic concepts necessary to understand network formation via click reactions, together with their main characteristics, are explained comprehensively. Some of the advanced applications of thermosets obtained by this methodology are also reviewed. Full article
(This article belongs to the Special Issue ‘Click’ Chemistry and Polymers)
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