Rapid and reliable determination of p-nitroaniline in wastewater by molecularly imprinted fluorescent polymeric ionic liquid microspheres.

Rapid and efficient detecting trace amount of environmental p-nitroaniline (p-NA) is in urgent need for security concerns and pollution supervision. In this work we report the use of molecularly imprinted polymeric ionic liquid (MIPIL) microspheres to construct recognizable surfaces for detection of p-NA through fluorescence quenching. The p-NA imprinted microspheres are synthesized by precipitation polymerization upon co-polymerization of 3-(anthracen-9-ylmethyl)-1-vinyl-1H-imidazol-3-ium chloride (Fluorescent IL monomer) with ethyleneglycol dimethacrylate (EGDMA). The electron-rich group alkenyl imidazole in IL functional monomer can dramatically improve the emission of anthracene fluorophore and the π-π stacking, electronic, and hydrogen bond between p-NA and MIPIL can efficiently enhance the selective recognition force. The as-synthesized MIPIL microspheres present spherical shape, high fluorescence emission intensity and specific recognition, which showed rapid detection rate (1min), stable reusable property (at least 4 time recycles), wonderful selectivity over several structural analogs, wide linear range (10nM to 10M) with a correlation coefficient of 0.992, and excellent sensitivity (LOD, 9nM). As synthesis and surface functionalization of MIPIL microspheres are well established, the methods reported in this work are facile, rapid and efficient for monitoring p-NA in environmental wastewater.

[1]  P. Wadgaonkar,et al.  Fluorescent polymeric ionic liquids for the detection of nitroaromatic explosives , 2014 .

[2]  Luigi Zeni,et al.  Detection of trinitrotoluene based on SPR in molecularly imprinted polymer on plastic optical fiber , 2013, Other Conferences.

[3]  Jianming Pan,et al.  Molecularly imprinted fluorescent hollow nanoparticles as sensors for rapid and efficient detection λ-cyhalothrin in environmental water. , 2016, Biosensors & bioelectronics.

[4]  E. Nesterov,et al.  Chemosensory performance of molecularly imprinted fluorescent conjugated polymer materials. , 2007, Journal of the American Chemical Society.

[5]  A. C. Beach,et al.  High-resolution anion-exchange and partition thin-layer chromatography for complex mixtures of 32P-postlabeled DNA adducts. , 1996, Journal of chromatography. B, Biomedical applications.

[6]  B. De Vivo,et al.  Sensitive Surface-Enhanced Raman Scattering (SERS) Detection of Nitroaromatic Pollutants in Water , 2014, Applied spectroscopy.

[7]  Y. Kawamura,et al.  [Migration of monomers and primary aromatic amines from nylon products]. , 2010, Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan.

[8]  Yan Zhao,et al.  Protein-mimetic, molecularly imprinted nanoparticles for selective binding of bile salt derivatives in water. , 2013, Journal of the American Chemical Society.

[9]  Xinpei Li,et al.  Development and Optimization of a SERS Method for On-site Determination of Nitrite in Foods and Water , 2014, Food Analytical Methods.

[10]  J. Sun,et al.  Determination of Acrylates in Wastewater by Dispersive Liquid-Liquid Microextraction Coupled to Capillary Gas Chromatography , 2014 .

[11]  Cem Önal,et al.  A review of the liquid chromatographic methods for the determination of biogenic amines in foods. , 2013, Food chemistry.

[12]  Xueying Tu,et al.  Molecularly Imprinted Polymer-Based Plasmonic Immunosandwich Assay for Fast and Ultrasensitive Determination of Trace Glycoproteins in Complex Samples. , 2016, Analytical chemistry.

[13]  Z. Altintas,et al.  Detection of Waterborne Viruses Using High Affinity Molecularly Imprinted Polymers. , 2015, Analytical chemistry.

[14]  M. Zanoni,et al.  Effect of Ionic Liquid on the Determination of Aromatic Amines as Contaminants in Hair Dyes by Liquid Chromatography Coupled to Electrochemical Detection , 2012, Molecules.

[15]  G. Wulff,et al.  Functional mimicry of carboxypeptidase A by a combination of transition state stabilization and a defined orientation of catalytic moieties in molecularly imprinted polymers. , 2008, Journal of the American Chemical Society.

[16]  K. Haupt,et al.  Toward the use of a molecularly imprinted polymer in doping analysis: selective preconcentration and analysis of testosterone and epitestosterone in human urine. , 2010, Analytical chemistry.

[17]  Anto James,et al.  Trace level detection of nitroanilines using a solution processable fluorescent porous organic polymer , 2016 .

[18]  P. Hauser,et al.  Capillary electrophoretic determination of different classes of organic ions by potentiometric detection with coated-wire ion-selective electrodes. , 1998, Analytical chemistry.

[19]  Xi Chen,et al.  High extraction efficiency for polar aromatic compounds in natural water samples using multiwalled carbon nanotubes/Nafion solid-phase microextraction coating. , 2009, Journal of chromatography. A.

[20]  M. Nascimento,et al.  Differential pulse voltammetric determination of 4-nitroaniline using a glassy carbon electrode: comparative study between cathodic and anodic quantification , 2015, Monatshefte für Chemie - Chemical Monthly.

[21]  Ming Yan,et al.  A Multiple‐Functional Ag/SiO2/Organic Based Biomimetic Nanocomposite Membrane for High‐Stability Protein Recognition and Cell Adhesion/Detachment , 2015 .

[22]  M. Jägerstad,et al.  Analysis of nonpolar heterocyclic amines in cooked foods and meat extracts using gas chromatography-mass spectrometry. , 1998, Journal of chromatography. A.

[23]  Bo Zhang,et al.  Ultrasensitive and selective assay of glutathione species in arsenic trioxide-treated leukemia HL-60 cell line by molecularly imprinted polymer decorated electrochemical sensors. , 2016, Biosensors & bioelectronics.

[24]  Jianrong Chen,et al.  A novel composite of molecularly imprinted polymer-coated PdNPs for electrochemical sensing norepinephrine. , 2015, Biosensors & bioelectronics.

[25]  P. He,et al.  Separation and determination of nitroaniline isomers by capillary zone electrophoresis with amperometric detection. , 2006, Talanta.

[26]  Laura Anfossi,et al.  A connection between the binding properties of imprinted and nonimprinted polymers: a change of perspective in molecular imprinting. , 2012, Journal of the American Chemical Society.

[27]  Hang Gong,et al.  A virus resonance light scattering sensor based on mussel-inspired molecularly imprinted polymers for high sensitive and high selective detection of Hepatitis A Virus. , 2017, Biosensors & bioelectronics.

[28]  Hongji Li,et al.  Optical detection of λ-cyhalothrin by core-shell fluorescent molecularly imprinted polymers in Chinese spirits. , 2015, Journal of agricultural and food chemistry.

[29]  Pengyan Wu,et al.  A cadmium(II)-based metal–organic framework for selective trace detection of nitroaniline isomers and photocatalytic degradation of methylene blue in neutral aqueous solution , 2016 .

[30]  Archana Jain,et al.  Simultaneous determination of ammonia, aliphatic amines, aromatic amines and phenols at μg l−1 levels in environmental waters by solid-phase extraction of their benzoyl derivatives and gas chromatography-mass spectrometry , 2001 .

[31]  Xuan Wang,et al.  Determination of primary aromatic amines using immobilized nanoparticles based surface-enhanced Raman spectroscopy , 2016 .

[32]  Kunpeng Guo,et al.  Simple and rapid detection of aromatic amines using a thin layer chromatography plate , 2010 .

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

[34]  T. Shih,et al.  Application of microwave-assisted desorption/headspace solid-phase microextraction as pretreatment step in the gas chromatographic determination of 1-naphthylamine in silica gel adsorbent. , 2007, Talanta.

[35]  A. Kuwahara,et al.  Molecularly imprinted tunable binding sites based on conjugated prosthetic groups and ion-paired cofactors. , 2009, Journal of the American Chemical Society.

[36]  Cuiping Han,et al.  Colorimetric detection of pollutant aromatic amines isomers with p-sulfonatocalix[6]arene-modified gold nanoparticles , 2009 .

[37]  Shoufang Xu,et al.  One-pot synthesis of mesoporous structured ratiometric fluorescence molecularly imprinted sensor for highly sensitive detection of melamine from milk samples. , 2015, Biosensors & bioelectronics.

[38]  F. Zhao,et al.  Sensitive Voltammetric Response of p-Nitroaniline on Single-Wall Carbon Nanotube-Ionic Liquid Gel Modified Glassy Carbon Electrodes , 2007 .

[39]  Meenakshi Singh,et al.  QCM sensing of melphalan via electropolymerized molecularly imprinted polythiophene films. , 2015, Biosensors & bioelectronics.

[40]  Qi Zhang,et al.  Molecularly imprinted polymer microspheres for optical measurement of ultra trace nonfluorescent cyhalothrin in honey. , 2014, Food chemistry.

[41]  M. Galceran,et al.  Hollow fibre-supported liquid membrane extraction and LC-MS/MS detection for the analysis of heterocyclic amines in urine samples. , 2009, Molecular nutrition & food research.

[42]  Guodong Li,et al.  Fluorescence detection of aromatic amines and photocatalytic degradation of rhodamine B under UV light irradiation by luminescent metal–organic frameworks , 2015 .