Click Functionalization of Well-Defined Copolymers Prepared by Atom Transfer Radical Polymerization

Sumerlin, Brent S.; Tsarevsky, Nicolay V.; Gao, Haifeng; Golas, Patricia L.; Louche, Guillaume; Lee, Robert Y.; Matyjaszewski, Krzysztof

doi:10.1021/bk-2006-0944.ch011

Cited by 16 publications

(12 citation statements)

References 1 publication

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“…Related (mini)reviews have appeared in recent literature dealing with the convergence of synthetic organic and polymer chemistry, 7 azide-alkyne cycloadditions in material science and organic chemistry, 39 the use of azide-alkyne cycloadditions as a universal ligation tool in polymer and materials science 40 as well as click functionalization of polymers prepared via atom transfer radical polymerization. 41 Nonetheless, this review distinguishes from the others by its focus on the construction of well-defined macromolecular architectures, which became readily available by the elegant utilization of click chemistry.…”

Section: David Fourniermentioning

confidence: 99%

Clicking polymers: a straightforward approach to novel macromolecular architectures

2007

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Living/controlled polymerization techniques have enabled the synthesis of a large variety of different well-defined (co)polymer structures. In addition, the use of click chemistry in polymer science is a quickly emerging field of research since it allows the fast and simple creation of well-defined and complex polymeric structures in yields that were previously unattainable. In this critical review, the application of the azide-alkyne 1,3-dipolar cycloaddition for the construction of well-defined polymer architectures will be discussed in detail, providing a comprehensive overview for all disciplines related to polymeric materials.

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Section: David Fourniermentioning

confidence: 99%

Clicking polymers: a straightforward approach to novel macromolecular architectures

2007

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“…Azide‐alkyne chemistry has a natural complementarily with ATRP,240, 253 as the polymer halogen end groups can be easily converted into azides 254–256. Azide‐alkyne chemistry and RAFT have also been combined,239, 246, 257 however, thiol‐ene chemistry would appear to display more complementarily with RAFT for building complex structures258 as the cleavage of RAFT and MADIX259 end groups yields thiols in the presence of primary or secondary amines,180, 186, 213, 260 dimethylphenyl phosphine,261 hydrazyne262 or sodium borohydrate 263.…”

Section: Raft Polymerizationmentioning

confidence: 99%

Characterization and electrical properties of methyl‐2‐hydroxyethyl cellulose doped with erbium nitrate salt

El‐Kader

Said

El-Naggar

et al. 2006

J of Applied Polymer Sci

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X-ray diffraction, infrared (IR), and electrical properties for pure and Er (NO 3 ) 3 -doped methyl-2-hydroxyethyl cellulose (MHEC) with concentrations of 0.5, 1, 2, 5, 7, and 10 wt % were studied. X-ray analysis indicates that the addition of Er (NO 3 ) 3 , which is a crystalline material, to MHEC at concentrations 10 and 13 wt % leads to the formation of crystalline phases in the amorphous polymeric matrix. The appearance of the bending mode n 2 and the combination mode (n 1 þ n 4 ) of Er (NO 3 ) 3 in the IR spectra of composite samples indicates the coordination of nitro group in the chains of MHEC. From the I-V characteristics, it was found that the charge transport mechanism in MHEC appears to be essentially space charge limited conduction, while the predominant mechanism in the composite samples is Poole-Frenkel. Values of both drift mobility (m) and the charge carrier density (n) has been reported. The temperature dependence conductivity data has been analyzed in terms of the Arrhenius and Mott's variable range hopping models. Different Mott's parameters such as the density of states, N(E F ), hopping distance (R), and average hopping energy (W) have been evaluated.

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“…The fastest reactions were observed for azides with electronwithdrawing substituents and less sterically congested end groups. macromolecular engineering, [34,35] model compounds of particular interest for a kinetic investigation include those that mimic the end groups of typical polymers such as polystyrene, poly(meth)acrylates, and polyacrylonitrile. [36][37][38][39] This report describes the reactivity of various azides with propargyl alcohol (PgOH) as a function of azide structure.…”

Section: Introductionmentioning

confidence: 99%

Structure–Reactivity Correlation in “Click” Chemistry: Substituent Effect on Azide Reactivity

Golas¹,

Tsarevsky²,

Matyjaszewski³

2008

Macromol. Rapid Commun.

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An investigation was conducted into substituent effects on azide reactivity during CuI‐catalyzed click reactions by reacting a variety of model azides with propargyl alcohol in DMF‐d7 using CuBr as catalyst, and monitoring conversions via 1H NMR. The model azides utilized for this investigation were selected due to structural similarity with the end groups of polymers typically employed in azide‐alkyne cycloadditions including polystyrene, poly(methyl acrylate), poly(methyl methacrylate), and polyacrylonitrile. Reactivities of alkyl azides depend on both the electronic properties of the substituent and steric congestion around the end group. The fastest reactions were observed for azides with electron‐withdrawing substituents and less sterically congested end groups.magnified image

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Click Functionalization of Well-Defined Copolymers Prepared by Atom Transfer Radical Polymerization

Cited by 16 publications

References 1 publication

Clicking polymers: a straightforward approach to novel macromolecular architectures

Clicking polymers: a straightforward approach to novel macromolecular architectures

Characterization and electrical properties of methyl‐2‐hydroxyethyl cellulose doped with erbium nitrate salt

Structure–Reactivity Correlation in “Click” Chemistry: Substituent Effect on Azide Reactivity

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