Construction of Linear Polymers, Dendrimers, Networks, and Other Polymeric Architectures by Copper‐Catalyzed Azide‐Alkyne Cycloaddition “Click” Chemistry

Johnson, Jeremiah A.; Finn, M. G.; Koberstein, Jeffrey T.; Turro, Nicholas J.

doi:10.1002/marc.200800208

Cited by 310 publications

(162 citation statements)

References 144 publications

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“…[461][462][463][464] The clickable functionality may be present in the monomers or on the Z or R groups of the RAFT agent (see Block Copolymers). The clickable monomers are incorporated as homopolymer blocks as a precursor to a polymer brush, or copolymerized to provide sites for attachment of functionality or for crosslinking.…”

Section: Raft Polymer Synthesesmentioning

confidence: 99%

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Living Radical Polymerization by the RAFT Process - A Second Update

Moad¹,

Rizzardo²,

Thang³

2009

Aust. J. Chem.

906

720

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This paper provides a second update to the review of reversible deactivation radical polymerization achieved with thiocarbonylthio compounds (ZC(=S)SR) by a mechanism of reversible addition-fragmentation chain transfer (RAFT) that was published in June 2005 (Aust. J. Chem. 2005, 58, 379-410). The first update was published in November 2006 (Aust. J. Chem. 2006, 59, 669-692). This review cites over 500 papers that appeared during the period mid-2006 to mid-2009 covering various aspects of RAFT polymerization ranging from reagent synthesis and properties, kinetics and mechanism of polymerization, novel polymer syntheses and a diverse range of applications. Significant developments have occurred, particularly in the areas of novel RAFT agents, techniques for end-group removal and transformation, the production of micro/nanoparticles and modified surfaces, and biopolymer conjugates both for therapeutic and diagnostic applications.

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Section: Raft Polymer Synthesesmentioning

confidence: 99%

“…[461][462][463][464] The RAFT process can be used to synthesize polymers with clickable moieties at the chain ends through the use of RAFT agents with appropriate functionality on 'Z' or 'R'. A significant number of these papers concern the combination of RAFT and azide-alkyne 1,3-dipolar cycloaddition.…”

Section: Click Reactionsmentioning

confidence: 99%

Living Radical Polymerization by the RAFT Process - A Second Update

Moad¹,

Rizzardo²,

Thang³

2009

Aust. J. Chem.

906

720

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“…The CuAAC reaction has also been used to 'click' modifications onto the 4-pyridyl position of terdentate ligands, such as dpa derivatives in order to synthesise metal chelators, 76 form Ln(III) luminescent probes, 77 and graft these onto silica nanoparticles. 78 There are many review articles covering this area, such as the use of the CuAAC reaction in construction of dendrimers and polymeric architectures, 79 modification of peptidomimetic oligomers, 80 and construction of higher order interlocked supramolecular structures. 81 Schibli et al described the installation of triazolyl metal chelating sites into molecules in a single step using the CuAAC reaction as the 'click to chelate' approach.…”

Section: Terdentate Ligandsmentioning

confidence: 99%

The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry

2014

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Ligands containing the btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] motif have appeared with increasing regularity over the last decade. This class of ligands, formed in a one pot 'click' reaction, has been studied for various purposes, such as for generating d and f metal coordination complexes and supramolecular self-assemblies, and in the formation of dendritic and polymeric networks, etc. This review article introduces btp as a novel and highly versatile terdentate building block with huge potential in inorganic supramolecular chemistry. We will focus on the coordination chemistry of btp ligands with a wide range of metals, and how it compares with other classical pyridyl and polypyridyl based ligands, and then present a selection of applications including use in catalysis, enzyme inhibition, photochemistry, molecular logic and materials, e.g. polymers, dendrimers and gels. The photovoltaic potential of triazolium derivatives of btp and its interactions with anions will also be discussed.

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“…Rev 2009, 109 (11), pp 5620-5686 It is sufficient to state that from the variety of click reactions available, the copper-catalyzed azide-alkyne 1,3-dipolar cycloaddition 14 has proven to be the most popular method employed. Nevertheless, the use of a toxic metal catalyst, i.e.…”

Section: Introductionmentioning

confidence: 99%

Limitations of radical thiol‐ene reactions for polymer–polymer conjugation

Koo

Stamenović

Ramaswamy

et al. 2010

J. Polym. Sci. A Polym. Chem.

240

228

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In the current work, we report our findings on the use of radical thiol-ene chemistry for polymerpolymer conjugation. The manuscript combines the results from the Preparative Macromolecular Chemistry group from Karlsruhe Institute of Technology (KIT) and the Polymer Chemistry Research group from Ghent University (UGent), which allowed for an investigation over a very broad range of reaction conditions. In particular, thermal and UV initiation methods for the 2 radical thiol-ene process were compared. In the KIT group, the process was studied as a tool for the synthesis of star polymers by coupling multi-functional thiol core molecules with poly(nbutyl acrylate) macromonomers (MM), employing thermally decomposing initiators. The product purity and thus reaction efficiency was assessed via electrospray ionization mass spectrometry. Although the reactions with 10 or 5 equivalents of thiol with respect to macromonomer were successful, the coupling reaction with a one-to-one ratio of MM to thiol yielded only a fraction of the targeted product, besides a number of side products. A systematic parameter study such as a variation of the concentration and nature of the initiator and the influence of thiol to ene ratio was carried out for a one-to-one ratio of MM to thiol content.Further experiments with poly(styrene) and poly(isobornyl acrylate) containing a vinylic end group confirmed that thermal thiol-ene conjugation is far from quantitative in terms of achieving macromolecular star formation. In parallel, the UGent group has been focusing on photo-initiated thiol-ene chemistry for the synthesis of functional polymers on the one hand and block copolymers consisting of poly(styrene) (PS) and poly(vinyl acetate) (PVAc) on the other hand.Various functionalization reactions showed an overall efficient thiol-ene process for conjugation reactions of polymers with low molecular weight compounds (~90% coupling yield). However, while SEC and FT-IR analysis of the conjugated PS-PVAc products indicated qualitative evidence for a successful polymer-polymer conjugation, 1 H NMR and elemental analysis revealed a low conjugation efficiency of about 23% for a thiol-to-ene ratio equal to one. Blank reactions using typical thiol-ene conditions indicated that bimolecular termination reactions 3 occur as competitive side reactions explaining why a molecular weight increase is observed even though the thiol-ene reaction was not successful. The extensive study of both research groups indicates that radical thiol-ene chemistry should not be proposed as a straightforward conjugation tool for polymer-polymer conjugation reactions. Head-to-head coupling is a major reaction pathway, which interrupts the propagation cycle of the thiol-ene process.

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Construction of Linear Polymers, Dendrimers, Networks, and Other Polymeric Architectures by Copper‐Catalyzed Azide‐Alkyne Cycloaddition “Click” Chemistry

Cited by 310 publications

References 144 publications

Living Radical Polymerization by the RAFT Process - A Second Update

Living Radical Polymerization by the RAFT Process - A Second Update

The btp [2,6-bis(1,2,3-triazol-4-yl)pyridine] binding motif: a new versatile terdentate ligand for supramolecular and coordination chemistry

Limitations of radical thiol‐ene reactions for polymer–polymer conjugation

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