Template synthesis of macromolecules. Synthesis and chemistry of functionalized macroporous poly(divinylbenzene)

Shea, Kenneth J.; Thompson, Evan A.; Pandey, Sue D.; Beauchamp, Philip S.

doi:10.1021/ja00529a044

Cited by 94 publications

(51 citation statements)

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“…10 Using this approach, 3a and 4a (1% m/v) were dissolved in a warm mixture of methyl methacrylate and //-butyl methacrylate (1:4, v/v) containing 0.5% (m/v) polymerization catalyst (benzoin ethyl ether), as adapted from the literature.11 Well defined aggregates with high aspect ratios were formed and gelated this solvent mixture. The organogel was transferred into gelatin cups and readily polymerized overnight with UV light {X = 365 nm) in a refrigerator (5 °C), yielding a rigid polymer matrix.…”

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confidence: 99%

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Hafkamp¹,

Kokke²,

Danke³

et al. 1997

Chem. Commun.

166

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confidence: 99%

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Hafkamp¹,

Kokke²,

Danke³

et al. 1997

Chem. Commun.

166

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“…The use of the imprinted recognition sites as potential chiral cavities for enantioselective synthesis was first described by the research groups of Shea 17 and Neckers, 18 and synthetic transformations including enantioselective protonation-deprotonation 19 and selective hydrolysis 20 have also been carried out in imprinted sites. However, perhaps the most elegant early work in this area was due to Wulff and co-workers, who targeted their initial studies to C-C bond formation in a biomimetic synthesis of aamino acids from glycine.…”

Section: "Microreactors" For Chiral Synthesismentioning

confidence: 99%

Imprinted Polymers: Versatile New Tools in Synthesis

Whitcombe

Alexander²,

Vulfson³

2000

Synlett

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Abstract:The use of molecularly imprinted polymers in synthetic organic chemistry is reviewed. These materials are prepared in the presence of a template for which they carry a functional and stereochemical "memory" and can be likened to artificial antibodies or enzymes. Their unique properties have been exploited by the use of imprinted polymers as stereo-and regio-selective solid supports in condensation reactions and hydride reduction, as protecting groups in the acylation of polyols and as catalysts to enhance the rates of reactions as diverse a Diels-Alder reaction, an Aldol condensation, β-elimination, the benzisoxazole isomerization, transesterification and ester hydrolyses.Key words: molecular imprinting, imprinted polymer, selectivity, chemical modification, synthesis IntroductionThe technique of molecular imprinting, in which a crosslinked polymer is assembled around a template, utilizing its interaction with functional monomers to create a recognition site, complementary in both shape and functionality to the original occupant, has become well established and many research groups are currently active in this field. [1][2][3][4][5][6][7][8][9][10][11] A schematic diagram of the imprinting process is shown in Figure 1.There have now been a number of examples illustrating the spectacular performance of imprinted polymers in a range of applications from chiral chromatographic separations 12-14 to the binding of ligands with a specificity rivaling that of antibodies. [15][16] However, it is becoming clear that the versatility of the imprinting methodology can be exploited to generate polymers for uses beyond those involving simply the recognition or separation of small organic molecules. In particular, researchers have begun to explore the use of imprinted polymers in synthesis, with a view to creating novel and robust reactive supports, as "protecting groups" and catalysts. In this short review we focus on the above applications, and outline some recent work which has taken the field of imprinted polymers into the realms of organic, inorganic, and biomimetic chemistry. "Microreactors" for chiral synthesisThe use of the imprinted recognition sites as potential chiral cavities for enantioselective synthesis was first described by the research groups of Shea 17 and Neckers, 18 and synthetic transformations including enantioselective protonation-deprotonation 19 and selective hydrolysis 20 have also been carried out in imprinted sites. However, perhaps the most elegant early work in this area was due to Wulff and co-workers, who targeted their initial studies to C-C bond formation in a biomimetic synthesis of aamino acids from glycine. 21 The model system set out by Wulff involved alkylation of a polymer-bound glycine, present as an ester enolate. The synthetic scheme on which this is based is shown in Figure 2, in which the glycine-Schiff base (1) is deprotonated to the enolate (2) amenable to alkylation via appropriate routes (alkyl halide, aldol condensation, Michael addition) to give the substituted amino...

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“…When the chemical structure of the template is strategically designed to resemble the transition state or an intermediate of a reaction, the molecular imprinting approach has been shown to allow the formation of threedimensional cavities within the polymeric matrix that display enzyme-like catalytic activity. The late 1980s saw important developments in the field of catalytic imprinted polymers, with seminal articles by Damen and Neckers [5] and Shea et al [6] on the stereocontrol of chemical reactions, by Wulff and Vietmeier [7] on enantioselective synthesis and by Leonhardt and Mosbach [8] on imprinting using substrate analogues. In 1989, Robinson and Mosbach [9] reported the first example of polymer imprinting using a transition-state analogue, and in the following years, reports in the literature flourished.…”

Section: Introductionmentioning

confidence: 99%

Molecularly imprinted polymers as biomimetic catalysts

Resmini

2012

Anal Bioanal Chem

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The quest for synthetic biomimetic catalysts able to complement the activity of enzymes has attracted substantial research efforts, and the molecular imprinting approach is one of the attractive techniques that are currently being investigated. In the last 3 years, there has been considerable interest in studying in greater detail the parameters that control and influence the catalytic activity of imprinted polymers and applying molecular imprinting to a wider range of polymeric matrices. This article reports on some of the interesting examples available in the literature regarding the use of metal-containing polymers, microgels and nanogels and thermoresponsive polymers.

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Template synthesis of macromolecules. Synthesis and chemistry of functionalized macroporous poly(divinylbenzene)

Cited by 94 publications

References 2 publications

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Organogel formation and molecular imprinting by functionalized gluconamides and their metal complexes

Imprinted Polymers: Versatile New Tools in Synthesis

Molecularly imprinted polymers as biomimetic catalysts

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