Synthesis of water-compatible surface-imprinted polymer via click chemistry and RAFT precipitation polymerization for highly selective and sensitive electrochemical assay of fenitrothion.

A novel water-compatible fenitrothion imprinted polymer was prepared on Au nanoparticles (AuNPs) by click chemistry and reversible addition-fragmentation chain transfer (RAFT) precipitation polymerization (RAFTPP). The RAFT chain-transfer agent was synthesized on the surface of AuNPs using click chemistry, then an imprinted polymer with hydrophilic polymer brushes was prepared on the RAFT chain-transfer agent modified AuNPs by RAFTPP, mediated by hydrophilic polyethylene glycol macromolecular cochain-transfer agent. The obtained molecularly imprinted material showed improved accessibility to fenitrothion and recognition property in water medium. When the material was immobilized on an ionic liquid functionalized graphene coated glassy carbon electrode for the electrochemical determination of fenitrothion, the resulting electrochemical sensor presented linear response in the range of 0.01-5 μM, with a sensitivity of 6.1 μA/μM mm(2). The low limit of detection was 8 nM (S/N=3). The sensor was successfully applied to the determination of real samples and the recovery for standard added was 95-108%.

[1]  Xubiao Luo,et al.  Novel molecularly imprinted polymer using 1-(α-methyl acrylate)-3-methylimidazolium bromide as functional monomer for simultaneous extraction and determination of water-soluble acid dyes in wastewater and soft drink by solid phase extraction and high performance liquid chromatography. , 2011, Journal of chromatography. A.

[2]  S. Inokuchi,et al.  Monolithic spin column extraction and GC-MS for the simultaneous assay of diquat, paraquat, and fenitrothion in human serum and urine , 2011, Analytical and bioanalytical chemistry.

[3]  Jinhuai Liu,et al.  A new “capturer” for electrochemical detection of organophosphate pesticides: The hydroxylation and carbonylation carbonaceous nanospheres , 2012 .

[4]  Surong Mei,et al.  Determination of trace 2,4-dinitrophenol in surface water samples based on hydrophilic molecularly imprinted polymers/nickel fiber electrode. , 2011, Biosensors & bioelectronics.

[5]  Xingyu Jiang,et al.  Visual detection of copper(II) by azide- and alkyne-functionalized gold nanoparticles using click chemistry. , 2008, Angewandte Chemie.

[6]  H. Eskandari,et al.  Preparation of magnetite/poly(styrene-divinylbenzene) nanoparticles for selective enrichment-determination of fenitrothion in environmental and biological samples. , 2012, Analytica chimica acta.

[7]  T. Kubo,et al.  Preparation of a novel molecularly imprinted polymer using a water-soluble crosslinking agent , 2005, Analytical and bioanalytical chemistry.

[8]  W. Binder,et al.  Click-chemistry for nanoparticle-modification , 2011 .

[9]  S. Inoue,et al.  A simple method for detecting fenitrothion, its metabolite 3-methyl-4-nitrophenol, and other organophosphorus pesticides in human urine by LC-MS , 2009, Forensic Toxicology.

[10]  Lingxin Chen,et al.  Molecularly imprinted polymers by reversible addition-fragmentation chain transfer precipitation polymerization for preconcentration of atrazine in food matrices. , 2011, Talanta.

[11]  Nora Unceta,et al.  Using a portable device based on a screen-printed sensor modified with a molecularly imprinted polymer for the determination of the insecticide fenitrothion in forest samples. , 2010 .

[12]  G. Pan,et al.  Narrowly dispersed hydrophilic molecularly imprinted polymer nanoparticles for efficient molecular recognition in real aqueous samples including river water, milk, and bovine serum. , 2013, Angewandte Chemie.

[13]  S. Admassie,et al.  Electrochemically pretreated glassy carbon electrode for electrochemical detection of fenitrothion in tap water and human urine , 2013 .

[14]  Hongyan He,et al.  Enhanced lysozyme imprinting over nanoparticles functionalized with carboxyl groups for noncovalent template sorption. , 2011, Analytical chemistry.

[15]  Limin Chang,et al.  Preparation of core-shell molecularly imprinted polymer via the combination of reversible addition-fragmentation chain transfer polymerization and click reaction. , 2010, Analytica chimica acta.

[16]  Lijuan Zhao,et al.  Preparation of surface-imprinted polymer grafted with water-compatible external layer via RAFT precipitation polymerization for highly selective and sensitive electrochemical determination of brucine. , 2014, Biosensors & bioelectronics.

[17]  G. Stucky,et al.  Facile RAFT precipitation polymerization for the microwave-assisted synthesis of well-defined, double hydrophilic block copolymers and nanostructured hydrogels. , 2007, Journal of the American Chemical Society.

[18]  Tianshu Zhou,et al.  A novel electrochemical sensor for determination of dopamine based on AuNPs@SiO2 core-shell imprinted composite. , 2012, Biosensors & bioelectronics.

[19]  W. Kutner,et al.  Surface development of molecularly imprinted polymer films to enhance sensing signals , 2013 .

[20]  G. Pan,et al.  Efficient one-pot synthesis of water-compatible molecularly imprinted polymer microspheres by facile RAFT precipitation polymerization. , 2011, Angewandte Chemie.

[21]  R. Madhuri,et al.  Multiwalled carbon nanotubes bearing 'terminal monomeric unit' for the fabrication of epinephrine imprinted polymer-based electrochemical sensor. , 2013, Biosensors & bioelectronics.

[22]  Huafeng Yang,et al.  Covalent functionalization of polydisperse chemically-converted graphene sheets with amine-terminated ionic liquid. , 2009, Chemical communications.

[23]  Panagiotis Manesiotis,et al.  Water-compatible imprinted polymers for selective depletion of riboflavine from beverages , 2009 .

[24]  Börje Sellergren,et al.  Water-compatible molecularly imprinted polymers obtained via high-throughput synthesis and experimental design. , 2003, Journal of the American Chemical Society.

[25]  T. Kubo,et al.  Novel surface modified molecularly imprinted polymer focused on the removal of interference in environmental water samples for chromatographic determination , 2005 .

[26]  Longhua Guo,et al.  A portable chemical sensor for histidine based on the strategy of click chemistry. , 2014, Biosensors & bioelectronics.

[27]  Shoufang Xu,et al.  Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. , 2011, Chemical Society reviews.

[28]  A. Kumaravel,et al.  A biocompatible nano TiO2/nafion composite modified glassy carbon electrode for the detection of fenitrothion , 2011 .

[29]  Lingxin Chen,et al.  Molecularly imprinted core-shell nanoparticles for determination of trace atrazine by reversible addition-fragmentation chain transfer surface imprinting , 2011 .

[30]  Jaime Ruiz,et al.  How to very efficiently functionalize gold nanoparticles by "click" chemistry. , 2008, Chemical communications.

[31]  Li Liu,et al.  Bioconjugation of biotin to the interfaces of polymeric micelles via in situ click chemistry. , 2009, Langmuir : the ACS journal of surfaces and colloids.

[32]  Tianshu Zhou,et al.  A molecularly imprinted polymer based on functionalized multiwalled carbon nanotubes for the electrochemical detection of parathion-methyl. , 2012, The Analyst.

[33]  Tania M. Gutiérrez Valencia,et al.  Determination of organophosphorus pesticides in bovine tissue by an on-line coupled matrix solid-phase dispersion-solid phase extraction-high performance liquid chromatography with diode array detection method. , 2011 .

[34]  S. Campidelli,et al.  Efficient covalent functionalisation of carbon nanotubes: the use of “click chemistry” , 2011 .

[35]  M. Courty,et al.  Magnetic Molecularly Imprinted Polymer Nanocomposites via Surface‐Initiated RAFT Polymerization , 2011 .

[36]  B. Hwang,et al.  Versatile Grafting Approaches to Functionalizing Individually Dispersed Graphene Nanosheets Using RAFT Polymerization and Click Chemistry , 2012 .

[37]  Changsheng Zhao,et al.  One-Pot Synthesis of Hydrophilic Molecularly Imprinted Nanoparticles , 2009 .

[38]  Shengshui Hu,et al.  Voltammetric Determination of Trace Amounts of Fenitrothion on a Novel Nano-TiO2 Polymer Film Electrode , 2004 .

[39]  Fan Zheng,et al.  Self-assembly of polystyrene with pendant hydrophilic gold nanoparticles: the influence of the hydrophilicity of the hybrid polymers , 2011 .

[40]  F. Zhao,et al.  Preparation and application of sunset yellow imprinted ionic liquid polymer − ionic liquid functionalized graphene composite film coated glassy carbon electrodes , 2014 .