An iterative route to “decorated” ethylene glycol-based linkers

Lu, Genliang; Lam, Sang Q.; Burgess, Kevin

doi:10.1039/b518061a

Cited by 54 publications

(42 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[30] By utilizing TEG fragments possessing an alkyne on one end and a tosylate on the other, the authors were able to repeatedly perform CuAAC followed by nucleophilic displacement of the tosylate with sodium azide to grow oligomers which then could be end-functionalized with any desired moiety via a final CuAAC step (R and R 0 in 30 could be varied). The water-solubility of these materials makes them attractive linkers for bioconjugation applications.…”

Section: Linear ''Click'' Polymers and Oligomers (From Small Moleculementioning

confidence: 99%

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

Johnson

Finn

Koberstein

et al. 2008

Macromol. Rapid Commun.

302

158

View full text Add to dashboard Cite

The enrichment of materials synthesis with the diverse chemical building blocks and functional groups of small molecule organic chemistry has been greatly accelerated in recent years by the introduction of the copper‐catalyzed azide‐alkyne cycloaddition (CuAAC). The efficiency and modular nature of this unique reaction enables materials chemists to prepare novel functional materials of unprecedented complexity. This review summarizes the application of CuAAC to the field of materials construction, defined here as the preparation of materials with architectural integrity dependent upon the triazole linkage. Recent examples, including linear polymers, dendrimers, polymer networks, polymeric nanoparticles, and other polymeric architectures, are described.magnified image

show abstract

Section: Linear ''Click'' Polymers and Oligomers (From Small Moleculementioning

confidence: 99%

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

Johnson

Finn

Koberstein

et al. 2008

Macromol. Rapid Commun.

302

158

View full text Add to dashboard Cite

show abstract

“…Bakbak et al [133] took a very similar approach to synthesis of polymers (e. g. 38, Figure 14). Lu et al [134] has described a stepwise iterative construction of a very regular triethylenglycol oligomer 40 ( Figure 15) using a tosyl group for the intermediate protection and activation for substitution with azide. Thus PhthN-CH 2 (CH 2 OCH 2 ) 2 CH 2 -N 3 reacted with propargyl tosyl triethyleneglycol under CuSO 4 /ascorbate conditions and after nucleophilic displacement with azide, the coupling cycle could be repeated twice to yield the trimer in 39% overall yield.…”

Section: Cuaac ''Click'' Polymerization Reactionsmentioning

confidence: 99%

Polymer “Clicking” by CuAAC Reactions

Meldal

2008

Macromol. Rapid Commun.

318

151

View full text Add to dashboard Cite

The CuAAC “click” reaction has developed as one of the most useful and widely employed reactions in ligation within polymer chemistry. This is due to the unique properties of the Cu(I) catalysis which renders the reaction quantitative even at low concentrations, orthogonal with other chemistries and extremely robust. The formed triazole on the other hand is of intermediate polarity and chemically and biochemically “invisible”, and the CuAAC provides the ideal “click” reaction for stitching together polymer architectures of unprecedended complexity as was it molecular LEGO. The CuAAC “clicking” in polymer chemistry is increasing exponentially and lead to highly defined polymer materials with novel properties.magnified image

show abstract

“…The synthesis of 1 initially focused on traditional methods. [23][24][25] However, 6 was obtained in very low yield (o20%). Most of the products were derived from the bromination of the benzene ring, which was confirmed by 1 H NMR and gas chromatography/mass spectrometry.…”

Section: Monomer Synthesesmentioning

confidence: 99%

“…Propargyl mono-terminated oligo(ethylene oxide)s (3) and azidomethyl pivalate were prepared using previously published methods. 24,25 Other reagents or materials were used as received.…”

Section: Experimental Procedures Materialsmentioning

confidence: 99%

Novel polyelectrolytes containing perfluorocyclobutane and triazole units: synthesis, characterization and properties

Zhu

Chen

2010

Polym J

View full text Add to dashboard Cite

A new class of aryl trifluorovinyl ether monomers were designed and synthesized, and novel fluorinated polymers containing perfluorocyclobutane and 1H-1,2,3-triazole units were prepared from these monomers. These polymers were characterized by nuclear magnetic resonance spectroscopy, thermo-gravimetric analysis and differential scanning calorimetry. The temperatures of 5% weight loss of the polymers under nitrogen were up to B290 1C, and the glass transition temperatures of the polymers were in the range of 79-110 1C. These new polymers showed good solubility in common organic solvents such as dimethyl sulfoxide and N,N-dimethylacetamide. In addition, the proton conductivity of the polymers was measured under anhydrous conditions using impedance spectroscopy, and a maximum conductivity of 2.85 lS cm À1 was obtained at 200 1C.

show abstract

An iterative route to “decorated” ethylene glycol-based linkers

Abstract: Iterative copper-catalyzed cycloadditions of azides to alkynes were used to join functionalized triethylene glycol molecules to give "linkers" of defined lengths equipped with several different end-group functionalities.

Cited by 54 publications

References 14 publications

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

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

Polymer “Clicking” by CuAAC Reactions

Novel polyelectrolytes containing perfluorocyclobutane and triazole units: synthesis, characterization and properties

Contact Info

Product

Resources

About