A high-performance and simple method for rapid and simultaneous determination of dihydroxybenzene isomers.

A novel idea on the basis of 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin (THPP) functionalized carbon nanotubes (CNTs) film was developed to simulate the chromatographic separation, which was able to rapidly and simultaneously detect dihydroxybenzene isomers based on their different oxidation potentials and corresponding currents. The mechanism involved in the recognition and isolation of the dihydroxybenzene isomers was explored and confirmed by UV spectra and density functional theory. It was proven that the current method for simultaneously detecting and isolating dihydroxybenzene isomers was ascribed to the priority of porphyrin film to induce oxidation of the three kinds of isomers, and the priority depends to a large extent on the different tendencies of dihydroxybenzene to interact with the peripheral hydroxyl group and with the extended π-conjugated ring of porphyrin. Most important of all, porphyrin functionalized CNTs film allows for the formation of well-defined interface and provides an advantageous and high-performance platform for the simultaneous determination and isolation of dihydroxybenzene isomers.

[1]  Su Lin,et al.  Porphyrin-Based Hole Conducting Electropolymer , 2008 .

[2]  A. Alizadeh,et al.  Polyfunctional tetrazolic thioethers through electrooxidative/Michael-type sequential reactions of 1,2- and 1,4-dihydroxybenzenes with 1-phenyl-5-mercaptotetrazole. , 2008, The Journal of organic chemistry.

[3]  D. Kuciauskas,et al.  Charge-transfer states determine iron porphyrin film third-order nonlinear optical properties in the near-IR spectral region , 2004 .

[4]  S. Kitagawa,et al.  Synthesis of functionalized porphyrins as oxygen ligand receptors. , 2003, The Journal of organic chemistry.

[5]  X. Lin,et al.  Determination of some catechol derivatives by a flow injection electrochemiluminescent inhibition method. , 2000, Talanta.

[6]  P. Cañizares,et al.  Electrochemical oxidation of hydroquinone, resorcinol, and catechol on boron-doped diamond anodes. , 2005, Environmental science & technology.

[7]  Ying Wang,et al.  Poly[meso-tetrakis(2-thienyl)porphyrin] for the sensitive electrochemical detection of explosives , 2010 .

[8]  H. Qi,et al.  Simultaneous Determination of Hydroquinone and Catechol at a Glassy Carbon Electrode Modified with Multiwall Carbon Nanotubes , 2005 .

[9]  Huangxian Ju,et al.  Functional multiwalled carbon nanotube nanocomposite with iron picket-fence porphyrin and its electrocatalytic behavior , 2007 .

[10]  Xiaoquan Lu,et al.  Direct Electron Transfer of Thiol-Derivatized Tetraphenylporphyrin Assembled on Gold Electrodes in an Aqueous Solution , 2009 .

[11]  H. Finklea,et al.  Passivation of pinholes in octadecanethiol monolayers on gold electrodes by electrochemical polymerization of phenol , 1990 .

[12]  M. Snook,et al.  Gel chromatographic isolation of catechols and hydroquinones , 1979 .

[13]  Xiaoquan Lu,et al.  SYNTHESIS AND CHARACTERIZATION OF THREE NEW UNSYMMETRICAL PORPHYRINS AND THEIR COBALT COMPLEXES , 2002 .

[14]  Pravin P Ingole,et al.  Self electro-catalysis of hydroquinone on gold electrode in aqueous un-buffered media , 2009 .

[15]  Lixian Sun,et al.  Prussian Blue electrodeposited on MWNTs-PANI hybrid composites for H(2)O(2) detection. , 2007, Talanta.

[16]  Guohua Zhao,et al.  Direct and Simultaneous Determination of Phenol, Hydroquinone and Nitrophenol at Boron-Doped Diamond Film Electrode , 2007 .

[17]  K. Kerman,et al.  Noncovalent modification of carbon nanotubes with ferrocene-amino acid conjugates for electrochemical sensing of chemical warfare agent mimics. , 2008, Analytical chemistry.

[18]  Xiaoquan Lu,et al.  Synthesis and Characterization of a Series of Thiol‐Derivatized Porphyrins and Electrocatalytic Reduction of Dioxygen by Cobalt(II)‐tetra‐[p‐(mercaptoprophyloxy)‐phenyl] Porphyrin (CoTMPP) on a Gold Support, Self‐Assembled Monolayers (SAMs) , 2006 .

[19]  M. Hoth,et al.  Redox Chemistry of Ca-Transporter 2-Palmitoylhydroquinone in an Artificial Thin Organic Film Membrane , 2007 .

[20]  B. A. White,et al.  Electrochemical polymerization of amino-, pyrrole-, and hydroxy-substituted tetraphenylporphyrins , 1987 .

[21]  Xueqin Zhou,et al.  Photoinduced energy and electron transfer in porphyrin-anthraquinone dyads bridged with a triazine group , 2010 .

[22]  Zhenhui Wang,et al.  Simultaneous determination of dihydroxybenzene isomers at single-wall carbon nanotube electrode , 2007 .

[23]  M. Oh,et al.  Supramolecular metal-organometallic coordination networks based on quinonoid pi-complexes. , 2004, Accounts of chemical research.

[24]  Xiaoquan Lu,et al.  Selective Anion Sensing through a Self-Assembled Monolayer of Thiol-End-Functionalized Porphyrin , 2009 .

[25]  D. Schiel,et al.  Electrochemistry of catechol terminated monolayers with Cu(II), Ni(II) and Fe(III) cations: a model for the marine adhesive interface. , 2008, Langmuir : the ACS journal of surfaces and colloids.

[26]  W. Schuhmann,et al.  Electrocatalytic reduction of oxygen at electropolymerized films of metalloporphyrins deposited onto multi-walled carbon nanotubes , 2009 .

[27]  Michael Beck,et al.  Predicting the site of electron transfer using DFT frontier orbitals: Studies on porphyrin attached either to quinone or hydroquinone, and quinhydrone self-assembled supramolecular complexes , 2006 .

[28]  M. Gray,et al.  Associative π−π Interactions of Condensed Aromatic Compounds with Vanadyl or Nickel Porphyrin Complexes Are Not Observed in the Organic Phase , 2008 .

[29]  Jae‐Joon Lee,et al.  Simultaneous Determination of Hydroquinone and Catechol at an Activated Glassy Carbon Electrode , 2010 .

[30]  Xiaoquan Lu,et al.  Investigation of the effects of metalloporphyrin species containing different substitutes on electron transfer at the liquid/liquid interface , 2006 .

[31]  Dong-Ming Zhao,et al.  Simultaneous determination of hydroquinone and catechol at PASA/MWNTs composite film modified glassy carbon electrode. , 2009, Colloids and surfaces. B, Biointerfaces.

[32]  Adriana G Lista,et al.  Determination of phenol, resorcinol and hydroquinone in air samples by synchronous fluorescence using partial least-squares (PLS). , 2006, Talanta.

[33]  R. Manderville,et al.  Oxidation of ochratoxin A by an Fe-porphyrin system: model for enzymatic activation and DNA cleavage. , 1999, Chemical research in toxicology.

[34]  T. Savenije,et al.  Spectroelectrochemical measurement of charge transport properties of electropolymerized tetrakis (hydroxyphenyl)porphyrins. , 1997 .

[35]  Z. Zeng,et al.  Solid-phase microextraction using fused-silica fibers coated with sol-gel-derived hydroxy-crown ether. , 2001, Analytical chemistry.

[36]  Diane K. Smith,et al.  Voltammetry of quinones in unbuffered aqueous solution: reassessing the roles of proton transfer and hydrogen bonding in the aqueous electrochemistry of quinones. , 2007, Journal of the American Chemical Society.

[37]  T. Okada,et al.  Ice chromatography. Characterization of water-ice as a chromatographic stationary phase. , 2006, Analytical chemistry.