Aryl diazonium salt surface chemistry and ATRP for the preparation of molecularly imprinted polymer grafts on gold substrates
Sarra Gam‐DerouichMinh Ngoc NguyenAhmed MadaniNaima MaouchePhilippe LangChristian PerruchotMohamed M. Chehimi
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Abstract Quercetin‐imprinted poly(vinyl pyridine‐co‐ethylene glycol dimethacrylate) cross‐linked grafts were prepared by atom transfer radical polymerization (ATRP) using aryl modified gold substrates as macroinitiators. The aryl layers were first attached to Au by electrochemical reduction of the diazonium salt BF $_{4}^{-}$ , + N 2 ‐C 6 H 4 ‐CH 2 CH 2 ‐OH. The resulting Au‐C 6 H 4 ‐CH 2 CH 2 ‐OH plates (Au‐OH) were further treated with 2‐bromopropionyl bromide (Br‐C(O)C(CH 3 ) 2 ‐Br) in order to attach ATRP initiator sites to Au‐OH, thus yielding Au‐C 6 H 4 ‐CH 2 CH 2 ‐OC(O)C(CH 3 ) 2 ‐Br (Au‐Br). 4‐Vinyl pyridine (4VP, functional monomer) and ethylene glycol dimethacrylate (EGDMA, cross‐linking monomer) were co‐polymerized in acetonitrile at room temperature in the presence of quercetin as a template molecule. Quercetin was then solvent‐extracted to obtain Au‐grafted molecularly imprinted polymer (Au‐MIP). The gold‐grafted nonimprinted polymer film (Au‐NIP) was prepared as a control substrate. The changes in the surface chemical composition, from the neat Au to Au‐MIP and Au‐NIP, were monitored by XPS and polarization modulation infrared reflection‐absorption spectroscopy (PM‐IRRAS). Cyclic voltammetry (CV) was used to assess the specificity and selectivity of Au‐MIP to detect quercetin. The detection limit was found to be better than 10 −6 mol/l with CV. Using square wave stripping voltammetry (SWSV), the detection limit was found to be as low as 10 −9 mol/l. Copyright © 2010 John Wiley & Sons, Ltd.Keywords:
Ethylene glycol dimethacrylate
Molecularly imprinted polymer
Atom-transfer radical-polymerization
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In the present study, a novel and efficient adsorbent constructed of molecularly imprinted polymer on the surface of modified magnetic nanoparticles with oleic acid (MNPs) was applied for the selective extraction of ezetimibe. The magnetic molecularly imprinted polymer (MMIP) was polymerized at the surface of modified MNPs using methacrylic acid as functional monomer, ezetimibe as template and ethylene glycol dimethacrylate as cross-linker. The resulting MMIP showed high adsorption capacity, good selectivity and fast kinetic binding for the template molecule. It was characterized by Fourier transform infrared analysis, scanning electron microscopy and transmission electron microscopy methods. The maximum adsorption capacity of MMIP was obtained as 137.1 mg g-1 and it took about 20 min to achieve the equilibrium state. The adsorption model of the adsorbent was fitted with the Freundlich and Langmuir isotherm equations. The assay exhibited a linear range of 0.003-20.000 mg L-1 for ezetimibe with a correlation coefficient of 0.995. The relative standard deviations for the recoveries were <5.2. The method was also examined for the analysis of ezetimibe in the biological samples.
Molecularly imprinted polymer
Ethylene glycol dimethacrylate
Molecular imprinting
Langmuir adsorption model
Ezetimibe
Precipitation polymerization
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Ethylene glycol dimethacrylate
Molecularly imprinted polymer
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Molecularly imprinted polymer
Ethylene glycol dimethacrylate
Solid phase extraction
Molecular imprinting
Precipitation polymerization
Bulk polymerization
Sample Preparation
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Molecularly imprinted polymer
Ethylene glycol dimethacrylate
Molecular imprinting
Precipitation polymerization
Surface Modification
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Salicylic acid(SA)molecularly imprinted polymers were synthesized with SA as the template,acrylamide as the functional monomer and ethylene glycol dimethacrylate as the cross-linker.In the buffer solution the adsorption of the polymers was tested by the differential pulse voltammetry.The equilibrium binding experiment results show that the adsorption capacity of SA molecularly imprinted polymers is much higher than that of non-molecularly-imprinted polymers.The selectivity of SA molecularly imprinted polymers was evaluated on the basis of dimethacrylate which has some similar molecular structures.The test confirms that the adsorption of SA molecularly imprinted polymers to SA is always higher than that to4-hydroxybenzoic acid,and salicylic acid molecularly imprinted polymers have a good selectivity for SA.
Molecularly imprinted polymer
Ethylene glycol dimethacrylate
Differential pulse voltammetry
Molecular imprinting
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Electrochemical molecularly imprinted polymers (e-MIP) are MIP specially designed to detect aromatic organic molecules without redox properties. The detection is based on the electrochemical answer of a redox probe inserted inside the binding cavities of cross-linked MIPs. Microbeads of e-MIP were synthesized from vinylferrocene or ferrocenylmethyl methacrylate as functional monomer/redox probe with or without 4-vinylpyridine functional as co-monomer, benzo[a]pyrene or bisphenol A as the target and ethylene glycol dimethacrylate of divinylbenzene as cross-linker. After physico-chemical characterization, e-MIP microbeads were incorporated in a graphite paste to prepare modified electrode or screen-printed carbon electrodes (SPCE).
Molecularly imprinted polymer
Ethylene glycol dimethacrylate
Electrochemical gas sensor
Divinylbenzene
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Molecularly imprinted polymer
Ethylene glycol dimethacrylate
Precipitation polymerization
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The development of sensitive and selective robust sensor materials for targeted biomarker detection aims to contribute to self-health monitoring and management. Molecularly imprinted polymeric (MIP) materials can perform as biomimetic recognition elements via tailored routes of synthesis for specific target analyte extraction and/or detection. In this work, a sensitive- and selective-lactate MIP has been developed utilizing methacrylic acid and ethylene glycol dimethacrylate as the functional monomer and cross-linker, respectively. The sensitivity of the as-synthesized imprinted species was evaluated by determining the target analyte retention, imprinting factor, and selectivity adsorption of up to 63.5%, 6.86, and 0.82, respectively. MIP selectivity elucidated the imprinting mechanism between the functional monomers and target analyte lactate, further experimentally evidenced by using structurally competitive analytes malic acid and sodium 2-hydroxybutyrate, where retentions of 22.6 and 25.2%, respectively, were observed. Understanding the specific intermolecular mechanisms of both the template analyte and structural interferents with the MIP enables experimentalists to make informed decisions regarding monomer-target and porogen selections and possible sites of interaction for improved molecular imprinting. This imprinting system highlights the potential to be further developed into artificial receptor sensor materials for the detection of disease.
Ethylene glycol dimethacrylate
Molecularly imprinted polymer
Molecular imprinting
Molecular Recognition
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Chronoamperometry
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Molecularly imprinted polymer(MIP) was prepared under different ratios between template molecular and functional monomer.The MIP was synthesized by the method of bulk polymerization,using 1-aminohy-dantoin(AHD),methacrylic acid(MAA) and ethylene glycol dimethacrylate(EDMA) as template molecular,functional monomer and cross-linker,respectively,and the absorption ability of MIP on template molecular was studied.Scatchard analysis also indicated the imprinted polymer using MAA as functional monomer could form one kind of binding site by noncovalent interactions and its dissociation constant was 4.33mmol/L.
Molecularly imprinted polymer
Ethylene glycol dimethacrylate
Molecular imprinting
Dissociation constant
Molecular Recognition
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