Biogenic amine vapour detection using poly(anilineboronic acid) films

Abstract Poly(anilineboronic acid) films were electrochemically deposited onto gold interdigitated arrays and employed as vapour detectors. Exposure to butylamine resulted in an increase in the measured resistance of the films and was compared to the response of polyaniline films under identical conditions. Temporal differential resistance measurements allowed for desirable signal characteristics and facilitated the monitoring of film response to analyte. The vapor detectors were able to respond to concentrations of butylamine as low as 10 ppb, 10-fold lower than the reported human detection thresholds of 0.1–1 ppm. The differences in the nature of response for both polyaniline and poly(anilineboronic acid) suggest that the boronic acid functionality plays an important role in the temporal response of the detector. UV–vis and polarization modulated infrared reflectance absorbance spectroscopy suggest that electrostatic interactions are occurring between boronic acid and volatile amines, resulting in the temporal differences in the response characteristics.

[1]  A. Heeger,et al.  Poly-p-phenyleneamineimine: synthesis and comparison to polyaniline , 1987 .

[2]  G. Preti,et al.  Analysis of lung air from patients with bronchogenic carcinoma and controls using gas chromatography-mass spectrometry. , 1988, Journal of chromatography.

[3]  R. Doty,et al.  Biochemical profile or uremic breath. , 1977, The New England journal of medicine.

[4]  V. Davidson,et al.  Amperometric detection of histamine with a methylamine dehydrogenase polypyrrole-based sensor. , 2000, Analytical chemistry.

[5]  Y. H. Kim,et al.  Localized charged excitations in polyaniline: Infrared photoexcitation and protonation studies , 1989 .

[6]  J. P. Bowen,et al.  Ab initio and molecular mechanics (MM3) calculations on alkyl‐ and arylboronic acids , 1998 .

[7]  J. M. Landete,et al.  Biogenic amines in wines from three Spanish regions. , 2005, Journal of agricultural and food chemistry.

[8]  M. Kontominas,et al.  On-line solid-phase extraction with surfactant accelerated on-column derivatization and micellar liquid chromatographic separation as a tool for the determination of biogenic amines in various food substrates. , 2004, Analytical chemistry.

[9]  Antonio J. Ricco,et al.  Resistance of polyaniline films as a function of electrochemical potential and the fabrication of polyaniline-based microelectronic devices , 1985 .

[10]  Dali Yang,et al.  Physical Stabilization or Chemical Degradation of Concentrated Solutions of Polyaniline Emeraldine Base Containing Secondary Amine Additives , 2002 .

[11]  Jun Kameoka,et al.  Polymeric Nanowire Chemical Sensor , 2004 .

[12]  M. Wan,et al.  Mechanism of proton doping in polyaniline , 1995 .

[13]  R. I. Baxter,et al.  Olfactory properties of Amines and n-Butanol , 1978 .

[14]  Helmut Neugebauer,et al.  Structural and electronic transitions in polyaniline: A Fourier transform infrared spectroscopic study , 1990 .

[15]  W. Qin,et al.  Optical sensor for amine vapors based on dimer-monomer equilibrium of indium(III) octaethylporphyrin in a polymeric film. , 2003, Analytical chemistry.

[16]  M. Freund,et al.  Potentiometric sensors based on the inductive effect on the pK(a) of poly(aniline): a nonenzymatic glucose sensor. , 2001, Journal of the American Chemical Society.

[17]  J. Simonet,et al.  New Boronic-Acid- and Boronate-Substituted Aromatic Compounds as Precursors of Fluoride-Responsive Conjugated Polymer Films , 2000 .

[18]  R. L. Elsenbaumer,et al.  Handbook of conducting polymers , 1986 .

[19]  I. Harada,et al.  Vibrational spectra and structure of polyaniline and related compounds , 1989 .

[20]  G. Sotzing,et al.  Conductive Polymer Foams as Sensors for Volatile Amines. , 2003 .

[21]  Wu-Song Huang,et al.  Polyaniline, a novel conducting polymer. Morphology and chemistry of its oxidation and reduction in aqueous electrolytes , 1986 .

[22]  David Ofer,et al.  Potential dependence of the conductivity of highly oxidized polythiophenes, polypyrroles, and polyaniline: Finite windows of high conductivity , 1990 .

[23]  M. Freund,et al.  A switchable self-doped polyaniline: interconversion between self-doped and non-self-doped forms. , 2004, Journal of the American Chemical Society.

[24]  Yukio Furukawa,et al.  Vibrational Spectra and Structure of Polyaniline , 1988 .

[25]  S. Wiberley,et al.  Introduction to infrared and Raman spectroscopy , 1965 .

[26]  B. Fabre,et al.  Poly(aniline boronic acid)-based conductimetric sensor of dopamine. , 2003, Chemical communications.

[27]  T M Hellman,et al.  Characterization of the odor properties of 101 petrochemicals using sensory methods. , 1974, Journal of the Air Pollution Control Association.

[28]  Michael S Freund,et al.  Potentiometric saccharide detection based on the pK(a) changes of poly(aniline boronic acid). , 2002, Journal of the American Chemical Society.

[29]  G M Shepherd,et al.  Time course of the membrane current underlying sensory transduction in salamander olfactory receptor neurones. , 1990, The Journal of physiology.

[30]  M. Freund,et al.  Electroactivity of electrochemically synthesized poly(aniline boronic acid) as a function of pH: Role of self-doping , 2004 .

[31]  E. Conwell,et al.  Localized molecular excitons in polyaniline , 1986 .

[32]  L. Elviri,et al.  Rapid assay for analyzing biogenic amines in cheese: matrix solid-phase dispersion followed by liquid chromatography-electrospray-tandem mass spectrometry. , 2005, Journal of agricultural and food chemistry.

[33]  Stuart I. Yaniger,et al.  “Polyaniline”: Interconversion of Metallic and Insulating Forms , 1985 .

[34]  Shoko Iwaki,et al.  Real-time monitoring of histamine released from rat basophilic leukemia (RBL-2H3) cells with a histamine microsensor using recombinant histamine oxidase. , 2002, Analytical biochemistry.

[35]  A. Heeger,et al.  Phenyl-capped octaaniline (COA): an excellent model for polyaniline , 1986 .

[36]  S. Firestein.  Electrical signals in olfactory transduction , 1992, Current Opinion in Neurobiology.

[37]  Ye,et al.  Spectroscopy and defect states in polyaniline. , 1990, Physical review. B, Condensed matter.

[38]  Y. H. Kim,et al.  Photoinduced localized charged excitations in polyaniline , 1988 .