A novel quercetin electrochemical sensor based on molecularly imprinted poly(para-aminobenzoic acid) on 3D Pd nanoparticles-porous graphene-carbon nanotubes composite

Abstract A novel molecularly imprinted electrochemical sensor for quercetin (QR) was fabricated via electropolymerization of para -aminobenzoic acid (p-ABA) on a three-dimensional (3D) Pd nanoparticles-porous graphene-carbon nanotubes composite (Pd/pGN-CNTs) modified glassy carbon electrode. The 3D Pd/pGN-CNTs composite was prepared by a facile one-pot hydrothermal method and it exhibited high conductivity, large surface as well as excellent electrocatalysis. The imprinting factor (IF) of MIP sensor toward QR was 3.14, which is higher than those of its analogues (i. e. morin, catechin, rutin, luteolin, and kaempferide). Based on the synergistic effect of the nanocomposite and the molecularly imprinted poly(p-ABA), the resulting electrochemical sensor presented high sensitivity and selectivity. Its linear response range was 0.01–0.50 μM, and the low detection limit was 5.0 nM (S/N = 3). The sensor also showed good reproducibility and stability. It was successfully applied to the detection of QR in food and medicine samples. In addition, theoretical calculations based on density functional theory (DFT) was conducted, and the result indicated that there was strong hydrogen bond between the QR and p-ABA.

[1]  R. Ruoff,et al.  Carbon-Based Supercapacitors Produced by Activation of Graphene , 2011, Science.

[2]  Lin Jiang,et al.  Mild and novel electrochemical preparation of β-cyclodextrin/graphene nanocomposite film for super-sensitive sensing of quercetin. , 2014, Biosensors & bioelectronics.

[3]  Q. Ma,et al.  Synthesis of Water-Dispersible Molecularly Imprinted Electroactive Nanoparticles for the Sensitive and Selective Paracetamol Detection. , 2016, ACS applied materials & interfaces.

[4]  Yuzhi Wang,et al.  Preparation of molecular imprinted polymers using bi-functional monomer and bi-crosslinker for solid-phase extraction of rutin. , 2012, Talanta.

[5]  Cheol-Woong Yang,et al.  Evidence of graphitic AB stacking order of graphite oxides. , 2008, Journal of the American Chemical Society.

[6]  S. Luo,et al.  Three-Dimensional Nitrogen-Doped Reduced Graphene Oxide-Carbon Nanotubes Architecture Supporting Ultrafine Palladium Nanoparticles for Highly Efficient Methanol Electrooxidation. , 2015, Chemistry.

[7]  Jingkun Xu,et al.  Electrochemical determination of quercetin by self-assembled platinum nanoparticles/poly(hydroxymethylated-3,4-ethylenedioxylthiophene) nanocomposite modified glassy carbon electrode , 2014 .

[8]  Hao Zhong,et al.  Pd–Fe3O4@C hybrid nanoparticles: preparation, characterization, and their high catalytic activity toward Suzuki coupling reactions , 2012 .

[9]  Zhenyang Wang,et al.  Imprinting of Molecular Recognition Sites on Nanostructures and Its Applications in Chemosensors , 2008, Sensors.

[10]  C. Chen,et al.  Facile and Green Synthesis of Palladium Nanoparticles-Graphene-Carbon Nanotube Material with High Catalytic Activity , 2013, Scientific Reports.

[11]  F. Zhao,et al.  3D porous graphene-porous PdCu alloy nanoparticles-molecularly imprinted poly(para-aminobenzoic acid) composite for the electrocatalytic assay of melamine. , 2014, ACS applied materials & interfaces.

[12]  Yanzhi Xia,et al.  Molecularly imprinted electrochemical sensor based on an electrode modified with an imprinted pyrrole film immobilized on a β-cyclodextrin/gold nanoparticles/graphene layer , 2015 .

[13]  Kangbing Wu,et al.  Activated silica gel based carbon paste electrodes exhibit signal enhancement for quercetin , 2012 .

[14]  Maciej Cieplak,et al.  Early diagnosis of fungal infections using piezomicrogravimetric and electric chemosensors based on polymers molecularly imprinted with d-arabitol. , 2016, Biosensors & bioelectronics.

[15]  F. Zhao,et al.  Electrochemical determination of cefotaxime based on a three-dimensional molecularly imprinted film sensor. , 2014, Biosensors & bioelectronics.

[16]  M. Muti,et al.  Electrochemical polymerized 5-amino-2-mercapto-1,3,4-thiadiazole modified single use sensors for detection of quercetin. , 2013, Colloids and surfaces. B, Biointerfaces.

[17]  Fanyong Yan,et al.  Highly luminescent organosilane-functionalized carbon dots as a nanosensor for sensitive and selective detection of quercetin in aqueous solution. , 2015, Talanta.

[18]  Xingguo Chen,et al.  One-step synthesis of three-dimensional graphene/multiwalled carbon nanotubes/Pd composite hydrogels: an efficient recyclable catalyst for Suzuki coupling reactions , 2015 .

[19]  O. Texier,et al.  Bioavailability, metabolism and physiological impact of 4-oxo-flavonoids , 1996 .

[20]  Si Sun,et al.  A Molecularly Imprinted Polymer with Incorporated Graphene Oxide for Electrochemical Determination of Quercetin , 2013, Sensors.

[21]  B. Zeng,et al.  Electrochemical sensors of octylphenol based on molecularly imprinted poly(3,4-ethylenedioxythiophene) and poly(3,4-ethylenedioxythiophene–gold nanoparticles) , 2015 .

[22]  M. Jaroniec,et al.  Hierarchically porous graphene-based hybrid electrodes with excellent electrochemical performance , 2013 .

[23]  Wensheng Huang,et al.  Electrode modified with porous alumina microfibers as a highly sensitive electrochemical sensor for quercetin , 2015 .

[24]  Aicheng Chen,et al.  Palladium-Based Nanomaterials: Synthesis and Electrochemical Applications. , 2015, Chemical reviews.

[25]  Steven C Zimmerman,et al.  Synthetic hosts via molecular imprinting--are universal synthetic antibodies realistically possible? , 2004, Chemical communications.

[26]  C. Peng,et al.  Quercetin and ferulic acid aggravate renal carcinoma in long-term diabetic victims. , 2010, Journal of agricultural and food chemistry.

[27]  W. Kutner,et al.  Electrochemically synthesized polymers in molecular imprinting for chemical sensing , 2012, Analytical and Bioanalytical Chemistry.

[28]  Lei Shang,et al.  Sensitive voltammetric determination of vanillin with an AuPd nanoparticles-graphene composite modified electrode. , 2014, Food chemistry.

[29]  M. L. Yola,et al.  A novel voltammetric sensor based on gold nanoparticles involved in p-aminothiophenol functionalized multi-walled carbon nanotubes: Application to the simultaneous determination of quercetin and rutin , 2014 .

[30]  Rui Wang,et al.  Ultrathin single-walled carbon nanotube network framed graphene hybrids. , 2015, ACS applied materials & interfaces.

[31]  Xianwen Kan,et al.  CD/AuNPs/MWCNTs based electrochemical sensor for quercetin dual-signal detection. , 2016, Biosensors & bioelectronics.

[32]  Sergey A. Piletsky,et al.  MIP sensors – the electrochemical approach , 2012, Analytical and Bioanalytical Chemistry.

[33]  Xin Zhao,et al.  Flexible holey graphene paper electrodes with enhanced rate capability for energy storage applications. , 2011, ACS nano.

[34]  Lite Yang,et al.  Electrochemical determination of eugenol using a three-dimensional molecularly imprinted poly (p-aminothiophenol-co-p-aminobenzoic acids) film modified electrode , 2016 .

[35]  A. Solak,et al.  A novel voltammetric sensor based on p-aminothiophenol functionalized graphene oxide/gold nanoparticles for determining quercetin in the presence of ascorbic acid , 2013 .