Microwave-assisted synthesis of resveratrol imprinted polymers with enhanced selectivity

Schwarz, Lachlan J.; Potdar, Mahesh Kamalakar; Danylec, Basil; Boysen, Reinhard I; Hearn, Milton Thomas William

doi:10.1039/c4ay02518k

Cited by 27 publications

(17 citation statements)

References 13 publications

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“…With the working conditions used, a maximum retention capability q max ∼ 300 µmol/g is estimated for MIP7, which is much higher than the sorption capabilities reported in the bibliography for related systems. Indeed, q max ∼ 116 µmol/g [26], q max ∼ 20 µmol/g [27], q max ∼ 83 µmol/g [33] and q max ∼ 30 µmol/g [39] are examples of reported values for the maximum binding capacity of resveratrol in different MIPs, considering ACN as solvent (contribution of non-specific sites is included in these values). As expected, a smaller value q max ∼ 3 µmol/g was measured for the retention of resveratrol in a MIP choosing ethanol as solvent [32].…”

Section: Batch Sorptionmentioning

confidence: 99%

“…With the working conditions used, a maximum retention capability ~ 300 µmol/g is estimated for MIP7, which is much higher than the sorption capabilities reported in the bibliography for related systems. Indeed, ~ 116 µmol/g [26], ~ 20 µmol/g [27], ~ 83 µmol/g [33] and ~ 30 µmol/g [39] are examples of reported values for the maximum binding …”

Section: Batch Sorptionmentioning

confidence: 99%

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Development of Molecularly Imprinted Polymers to Target Polyphenols Present in Plant Extracts

et al. 2017

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Abstract:The development of molecularly imprinted polymers (MIPs) to target polyphenols present in vegetable extracts was here addressed. Polydatin was selected as a template polyphenol due to its relatively high size and amphiphilic character. Different MIPs were synthesized to explore preferential interactions between the functional monomers and the template molecule. The effect of solvent polarity on the molecular imprinting efficiency, namely owing to hydrophobic interactions, was also assessed. Precipitation and suspension polymerization were examined as a possible way to change MIPs morphology and performance. Solid phase extraction and batch/continuous sorption processes were used to evaluate the polyphenols uptake/release in individual/competitive assays. Among the prepared MIPs, a suspension polymerization synthesized material, with 4-vinylpyridine as the functional monomer and water/methanol as solvent, showed a superior performance. The underlying cause of such a significant outcome is the likely surface imprinting process caused by the amphiphilic properties of polydatin. The uptake and subsequent selective release of polyphenols present in natural extracts was successfully demonstrated, considering a red wine solution as a case study. However, hydrophilic/hydrophobic interactions are inevitable (especially with complex natural extracts) and the tuning of the polarity of the solvents is an important issue for the isolation of the different polyphenols.

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Section: Batch Sorptionmentioning

confidence: 99%

Section: Batch Sorptionmentioning

confidence: 99%

Development of Molecularly Imprinted Polymers to Target Polyphenols Present in Plant Extracts

et al. 2017

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“…In our previous studies, ( E )-resveratrol was employed as a template molecule for the preparation of several MIPs [2,3,4,15,16]. A variety of traditional methods have been reported [17,18,19,20,21,22] for the synthesis of ( E )-resveratrol.…”

Section: Resultsmentioning

confidence: 99%

The Application of Template Selectophores for the Preparation of Molecularly Imprinted Polymers

et al. 2015

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Abstract:Molecularly imprinted polymers are versatile materials with wide application scope for the detection, capture and separation of specific compounds present in complex feed stocks. A major challenge associated with their preparation has been the need to sacrifice one mole equivalent of the template molecule to generate the complementary polymer cavities that selectively bind the target molecule. Moreover, template molecules can often be difficult to synthesise, expensive or lack stability. In this study, we describe a new approach, directed at the use of synthetic selectophores, chosen as readily prepared and low cost structural analogues with recognition groups in similar three-dimensional arrangements as found in the target molecule. To validate the approach, a comparative study of selectophores related to the polyphenolic compound (E)-resveratrol has been undertaken using traditional and green chemical synthetic approaches. These molecular mimic compounds were employed as polymer templates and also as binding analytes to interrogate the recognition sites associated with the molecularly imprinted polymers. Importantly, the study confirms that the use of selectophores has the potential to confer practical advantages, including access to more efficient methods for selection and preparation of suitable template molecules with a broader range of molecular diversity, as well as delivering imprinted polymers capable of recognizing the target compound and structurally related products.

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“…Stationary phases for the separation of chiral compounds in CEC have traditionally been synthesized using a variety of matrix materials (i.e., polymeric resins, alumina, or silica) modified with an immobilized chiral selector, such as a polysaccharide, a macrocyclic antibiotic, a cyclodextrin, an amino acid, or a protein derivative . Alternatively, molecularly imprinted polymers (MIPs), containing nano‐cavities of predetermined shape and appropriate orientation of functional groups , can be employed as tailor‐made molecular recognition materials with selectivity towards a particular chiral compound . In contrast to the generic types of stationary phases which employ chiral selectors/auxiliaries, MIPs can be prepared without the need to incorporate expensive chiral selectors/auxiliaries into the polymer matrix, and require use of non‐chiral precursors (monomers) with a sacrificial chiral template to create enantio‐selective cavities through molecular self‐assembly processes that lead to pre‐polymerization complexes which can subsequently be cross‐linked around the target chiral template .…”

Section: Introductionmentioning

confidence: 99%

Use of peak sharpening effects to improve the separation of chiral compounds with molecularly imprinted porous polymer layer open‐tubular capillaries

et al. 2017

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This investigation demonstrates the application of a new peak sharpening technique to improve the separation of difficult-to-resolve racemic mixtures in capillary electro-chromatography. Molecularly imprinted porous layer open tubular (MIP-PLOT) capillaries, prepared by a layer-on-layer polymerization approach with Z-l-Asp-OH as the template, were selected to validate the approach. SEM revealed that the polymer film thickness can be varied by changes in both the polymer composition and the layer-on-layer regime. Capillaries made with methacrylic acid as the functional monomer could not separate the Z-Asp-OH racemate, due to weak interactions between the MIP-PLOT material and the target analytes. In contrast, MIP-PLOT capillaries prepared with 4-vinylpyridine as the functional monomer resulted in increased ionic interactions with the target analytes. Separation of the enantiomers could be enhanced when a peak zone sharpening effect was exploited through the use of specific BGE compositions and by taking advantage of eigenpeak phenomena. In this manner, the position of a sharpening zone and the peak shape of the sample analytes could be fine-tuned, so that when the sharpening zone and the target analyte co-migrated the separation of the Z-l-Asp-OH enantiomer from its d-enantiomer in a racemic mixture could be achieved under overloading conditions.

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Microwave-assisted synthesis of resveratrol imprinted polymers with enhanced selectivity

Cited by 27 publications

References 13 publications

Development of Molecularly Imprinted Polymers to Target Polyphenols Present in Plant Extracts

Development of Molecularly Imprinted Polymers to Target Polyphenols Present in Plant Extracts

The Application of Template Selectophores for the Preparation of Molecularly Imprinted Polymers

Use of peak sharpening effects to improve the separation of chiral compounds with molecularly imprinted porous polymer layer open‐tubular capillaries

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