Copper(i) mediated radical polymerisation of uridine and adenosine monomers on a silica support

Marsh, Andrew; Khan, Afzal; Garcia, Margarita; Haddleton, David M.

doi:10.1039/b005832g

Cited by 37 publications

(35 citation statements)

References 21 publications

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“…Oleic acid stabilized, superparamagnetic iron oxide nanoparticles (Fe 3 O 4 ) were synthesized via an aqueous method followed by extraction into an organic phase [31]. Magnetic nanoparticle supported ATRP initiators 3 were then synthesized by ligand exchange [31] with silane modified ATRP intiators [32]. Salen [33][34][35] (2a, 2b) and piperazine [36] (2c) modified styrene monomers were synthesized and polymerized via ATRP [31,35] to form the magnetic polymer brush (MPB) materials 4a and 4b and MPB catalyst 1c (Fig.…”

Section: Methodsmentioning

confidence: 99%

“…Oleic acid stabilized Fe 3 O 4 nanoparticles [31] and an ATRP initiator silane [32] were synthesized following published procedures. A dispersion of oleic acid stabilized Fe 3 O 4 nanoparticles in toluene (215 mL, 0.014 mg/mL, 3.01 g Fe 3 O 4 -OA) was combined with additional toluene (35 mL), ATRP initiator silane (3.01 g), and triethylamine (8.5 g) [31].…”

Section: Synthesis Of Atrp Initiator Functionalized Fe 3 O 4 Nanopartmentioning

confidence: 99%

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Magnetic Nanoparticle Polymer Brush Catalysts: Alternative Hybrid Organic/Inorganic Structures to Obtain High, Local Catalyst Loadings for Use in Organic Transformations

2009

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A new class of hybrid organic/inorganic molecular catalysts with high, local catalyst concentrations is demonstrated by supporting organic and organometallic catalysts on magnetic nanoparticle based polymer brushes (MPB). Poly(styrene) brushes containing Co(III)-salen or piperazine side chains are prepared via atom-transfer radical polymerization (ATRP) from Fe 3 O 4 nanoparticles modified with appropriate initiator molecules. The polymer brush architecture promotes the cooperative interactions required for Co-salen catalyzed ring-opening of epoxides as demonstrated in the hydrolytic kinetic resolution of racepichlorohydrin. In addition, the piperazine functionalized MPB catalyst contains the high catalyst concentration that is required for promoting the Knoevenagel condensation of benzaldehyde and malononitrile with this type of amine catalyst. All the MPB catalysts were easily removed from solution via application of a magnetic field, allowing straightforward recovery and reuse. The versatile MPB architecture can be used to create a variety of recoverable supported organic or organometallic catalysts.

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Section: Methodsmentioning

confidence: 99%

Section: Synthesis Of Atrp Initiator Functionalized Fe 3 O 4 Nanopartmentioning

confidence: 99%

Magnetic Nanoparticle Polymer Brush Catalysts: Alternative Hybrid Organic/Inorganic Structures to Obtain High, Local Catalyst Loadings for Use in Organic Transformations

2009

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“…1) in solution [34], and on a solid support [35]. Recently, there has been renewed interest in these types of polymers in order to use H-bonding to give sequence (and potentially stereo) control, single chain manipulation and controlled polymer folding using different controlled polymerization techniques [36], such as reversible addition-fragmentation chain transfer (RAFT) polymerization [37], nitroxidemediated polymerization [38] and ATRP [39][40][41].…”

Section: Introductionmentioning

confidence: 99%

Water soluble triblock and pentablock poly(methacryloyl nucleosides) from copper-mediated living radical polymerisation using PEG macroinitiators

Garcia

Beecham

Kempe

et al. 2015

European Polymer Journal

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a b s t r a c tThe monomers methacryloyl uridine and methacryloyl adenosine have been polymerised under copper-mediated living radical conditions using poly(ethylene glycol) (PEG) macroinitiators to give triblock and pentablock copolymers of reasonable dispersity. The triblocks were used as initiators for the successful synthesis of pentablock copolymers. The secondary structures of the triblock and pentablock copolymers have been investigated using circular dichroism (CD) spectroscopy. The adenosine copolymers are found to exhibit more ordered secondary structures in water in comparison to the uridine derived polymers. New supramolecular structure is observed by CD upon mixing adenosine and uridine triblock copolymers in water. The polymers obtained are of interest as potential drug delivery agents through interaction with small molecules and oligonucelotides.

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“…These methods allow the formation of well-defined polymer architectures in which a large variety of biological functionalities, such as nucleobases, can be included. 20,21 It is well known that amphiphilic block copolymers have the ability to assemble into multiple morphologies in solution. Depending on a number of parameters, such as the ratio of the hydrophilic and hydrophobic blocks, the morphology can vary from spherical micelles, rods, and vesicles to large compound micelles (LCMs).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and assembly behavior of nucleobase‐functionalized block copolymers

Spijker

Dirks

Hest

2006

J. Polym. Sci. A Polym. Chem.

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Block copolymers consisting of a poly(ethylene glycol) chain and a thymine‐ or adenine‐functional polymethacrylate block have been prepared with atom transfer radical polymerization, and their aggregation behavior in an aqueous medium has been studied. Upon the mixing of the two block copolymers, the critical aggregation concentration increases in comparison with the critical aggregation concentration of the individual block copolymers. It has therefore been demonstrated that the amphiphilic behavior of this class of block copolymers is affected by the interaction between the complementary nucleobases, which leads to an unexpected increase in the hydrophilicity of the block copolymer ensemble.

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Copper(i) mediated radical polymerisation of uridine and adenosine monomers on a silica support

Abstract: Copper(I) mediated radical polymerisation is used to polymerise uridine and adenosine substituted methacrylates onto a silica surface giving supported polymers with potential as re-usable templates and for interaction with nucleic acids.

Cited by 37 publications

References 21 publications

Magnetic Nanoparticle Polymer Brush Catalysts: Alternative Hybrid Organic/Inorganic Structures to Obtain High, Local Catalyst Loadings for Use in Organic Transformations

Magnetic Nanoparticle Polymer Brush Catalysts: Alternative Hybrid Organic/Inorganic Structures to Obtain High, Local Catalyst Loadings for Use in Organic Transformations

Water soluble triblock and pentablock poly(methacryloyl nucleosides) from copper-mediated living radical polymerisation using PEG macroinitiators

Synthesis and assembly behavior of nucleobase‐functionalized block copolymers

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