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Special Issue "Click Chemistry in Polymer Science"

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A special issue of Polymers (ISSN 2073-4360).

Deadline for manuscript submissions: closed (31 May 2011)

Special Issue Editor

Guest Editor
Prof. Dr. Andrew B. Lowe

Professor of Polymer Science & Nanochemistry, Nanochemistry Research Institute, Department of Chemistry, Faculty of Science & Engineering, Curtin University, Kent Street, Bentley, Perth, Western Australia 6102, Australia
Website | E-Mail
Phone: +61 8 9266 9281
Fax: +61 8 9266 2300
Interests: RAFT; ROMP; thiol-ene; click chemistry; water-soluble polymers; stimulus responsive polymers

Special Issue Information

Dear Colleagues,

Click chemistry, in its various guises, has, arguably, had a transformational impact on facile approaches to macromolecular modification. While the versatility and (bio)orthogonality of the Cu-catalyzed alkyne-azide reaction has been repeatedly demonstrated many other ‘click’ reactions are still very much in their infancy with respect to applications in macromolecular synthesis and modification.

This special issue of Polymers aims to highlight recent advances in the applications of ‘click’ chemistry in macromolecular science and will serve as a primary source for both new and experienced practitioners of these remarkable chemistries.

Prof. Dr. Andrew B. Lowe
Guest Editor

Keywords

  • ‘click’, alkyne-azide
  • thiol-ene
  • thiol-yne
  • functionalization
  • complex molecules

Published Papers (4 papers)

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Research

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Open AccessArticle Preparation of Novel Hydrolyzing Urethane Modified Thiol-Ene Networks
Polymers 2011, 3(4), 1849-1865; doi:10.3390/polym3041849
Received: 11 August 2011 / Revised: 6 October 2011 / Accepted: 21 October 2011 / Published: 25 October 2011
Cited by 2 | PDF Full-text (1124 KB) | HTML Full-text | XML Full-text
Abstract
Novel tetra-functional hydrolyzing monomers were prepared from the reaction of TEOS and select alkene-containing alcohols, ethylene glycol vinyl ether or 2-allyloxy ethanol, and combined with trimethylolpropane tris(3-mercaptopropionate) (tri-thiol) in a thiol-ene “click” polymerization reaction to produce clear, colorless thiol-ene networks using both radiation
[...] Read more.
Novel tetra-functional hydrolyzing monomers were prepared from the reaction of TEOS and select alkene-containing alcohols, ethylene glycol vinyl ether or 2-allyloxy ethanol, and combined with trimethylolpropane tris(3-mercaptopropionate) (tri-thiol) in a thiol-ene “click” polymerization reaction to produce clear, colorless thiol-ene networks using both radiation and thermal-cure techniques. These networks were characterized for various mechanical characteristics, and found to posses Tg’s (DSC), hardness, tack, and thermal stability (TGA) consistent with their molecular structures. A new ene-modified urethane oligomer was prepared based on the aliphatic polyisocyanate Desmodur® N 3600 and added to the thiol-ene hydrolyzable network series in increasing amounts, creating a phase-segregated material having two Tg’s. An increase in water absorption in the ene-modified urethane formulations leading to a simultaneous increase in the rate of hydrolysis was supported by TGA data, film hardness measurements, and an NMR study of closely related networks. This phenomenon was attributed to the additional hydrogen bonding elements and polar functionality brought to the film with the addition of the urethane segment. SEM was utilized for visual analysis of topographical changes in the film’s surface upon hydrolysis and provides support for surface-driven erosion. Coatings prepared in this study are intended for use as hydrolyzing networks for marine coatings to protect against ship fouling. Full article
(This article belongs to the Special Issue Click Chemistry in Polymer Science)
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Open AccessArticle Metal-Free Polymethyl Methacrylate (PMMA) Nanoparticles by Enamine “Click” Chemistry at Room Temperature
Polymers 2011, 3(4), 1673-1683; doi:10.3390/polym3041673
Received: 1 September 2011 / Revised: 15 September 2011 / Accepted: 6 October 2011 / Published: 7 October 2011
Cited by 17 | PDF Full-text (412 KB) | HTML Full-text | XML Full-text
Abstract
“Click” chemistry has become an efficient avenue to unimolecular polymeric nanoparticles through the self-crosslinking of individual polymer chains containing appropriate functional groups. Herein we report the synthesis of ultra-small (7 nm in size) polymethyl methacrylate (PMMA) nanoparticles (NPs) by the “metal-free” cross-linking of
[...] Read more.
“Click” chemistry has become an efficient avenue to unimolecular polymeric nanoparticles through the self-crosslinking of individual polymer chains containing appropriate functional groups. Herein we report the synthesis of ultra-small (7 nm in size) polymethyl methacrylate (PMMA) nanoparticles (NPs) by the “metal-free” cross-linking of PMMA-precursor chains prepared by reversible addition-fragmentation chain transfer (RAFT) polymerization containing b-ketoester functional groups. Intramolecular collapse was performed by the one-pot reaction of b-ketoester moieties with alkyl diamines in tetrahydrofurane at r.t. (i.e., by enamine formation). The collapsing process was followed by size exclusion chromatography and by nuclear magnetic resonance spectroscopy. The size of the resulting PMMA-NPs was determined by dynamic light scattering. Enamine “click” chemistry increases the synthetic toolbox for the efficient synthesis of metal-free, ultra-small polymeric NPs. Full article
(This article belongs to the Special Issue Click Chemistry in Polymer Science)
Figures

Open AccessArticle Cellulose Chemistry Meets Click Chemistry: Syntheses and Properties of Cellulose-Based Glycoclusters with High Structural Homogeneity
Polymers 2011, 3(1), 489-508; doi:10.3390/polym3010489
Received: 6 January 2011 / Accepted: 6 February 2011 / Published: 24 February 2011
Cited by 15 | PDF Full-text (967 KB) | HTML Full-text | XML Full-text
Abstract
b-1,4-Glucans having oligosaccharide appendages (O-/N-linked b-maltoside and O-/N-linked b-lactoside) at 6C positions of all repeating units can be readily prepared from cellulose through a two step strategy composed of: (1) regio-selective and quantitative bromination/azidation to afford
[...] Read more.
b-1,4-Glucans having oligosaccharide appendages (O-/N-linked b-maltoside and O-/N-linked b-lactoside) at 6C positions of all repeating units can be readily prepared from cellulose through a two step strategy composed of: (1) regio-selective and quantitative bromination/azidation to afford 6-azido-6-deoxycellulose; and (2) the subsequent Cu+-catalyzed coupling with oligosaccharides having terminal alkyne. The resultant cellulose derivatives showed improved water solubility in comparison to native cellulose; they, however, bound to carbohydrate-binding proteins in a rather non-specific manner. Molecular dynamics calculations revealed that these properties are attributable to rigid sheet-like structures of the cellulose derivatives and the subsequent exposure of their hydrophobic moieties to solvents. Full article
(This article belongs to the Special Issue Click Chemistry in Polymer Science)

Review

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Open AccessReview Polysaccharides: The “Click” Chemistry Impact
Polymers 2011, 3(4), 1607-1651; doi:10.3390/polym3041607
Received: 30 June 2011 / Revised: 23 August 2011 / Accepted: 9 September 2011 / Published: 27 September 2011
Cited by 34 | PDF Full-text (2117 KB) | HTML Full-text | XML Full-text
Abstract
Polysaccharides are complex but essential compounds utilized in many areas such as biomaterials, drug delivery, cosmetics, food chemistry or renewable energy. Modifications and functionalizations of such polymers are often necessary to achieve molecular structures of interest. In this area, the emergence of the
[...] Read more.
Polysaccharides are complex but essential compounds utilized in many areas such as biomaterials, drug delivery, cosmetics, food chemistry or renewable energy. Modifications and functionalizations of such polymers are often necessary to achieve molecular structures of interest. In this area, the emergence of the “click” chemistry concept, and particularly the copper-catalyzed version of the Huisgen 1,3-dipolar cycloaddition reaction between terminal acetylenes and azides, had an impact on the polysaccharides chemistry. The present review summarizes the contribution of “click” chemistry in the world of polysaccharides. Full article
(This article belongs to the Special Issue Click Chemistry in Polymer Science)

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