Selective fluorescence sensors for p-phenylenediamine using formyl boronate ester with an assistance of micelles

Sensors and Actuators, B: Chemical

Volumn 173, Issue , 2012, Pages 682-691

  Ngamdee, Kessarin ^a   Martwiset, Surangkhana ^a   Tuntulani, Thawatchai ^d   Ngeontae, Wittaya ^a,b,c  

^a Khon Kaen University   (Thailand)

^b KHON KAEN UNIVERSITY   (Thailand)

^c CENTER OF EXCELLENCE ON HAZARDOUS SUBSTANCE MANAGEMENT HSM   (Thailand)

^d CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Chemical sensors; Fluorescence sensors; Micelle; p Phenylenediamine

Indexed keywords

ALIZARIN RED; BORONATE ESTERS; BUFFER SOLUTIONS; CETYLTRIMETHYLAMMONIUM BROMIDE; CONCENTRATION RANGES; FLUORESCENCE EMISSION; FLUORESCENCE INTENSITIES; FLUORESCENCE QUENCHING; FLUORESCENCE SENSORS; HIGH SENSITIVITY; HYDROPHOBIC CORE; LINEAR FUNCTIONS; OPTIMUM CONDITIONS; P-PHENYLENE DIAMINES; PHOSPHATE BUFFER SOLUTIONS; PRIMARY AMINES; SELECTIVE FLUORESCENCE; SENSOR MOLECULES; SOLUTION PH; SPIKED WATER SAMPLES; SURFACTANT CONCENTRATIONS;

CALIBRATION; CHEMICAL SENSORS; ESTERIFICATION; ESTERS; FLUORESCENCE; MICELLES; SURFACE ACTIVE AGENTS;

SENSORS;

EID: 84867071543     PISSN: 09254005     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.snb.2012.07.077     Document Type: Article

References (38)

1. G.J. Nohynek, R. Fautz, F. Benech-Kieffer, and H. Toutain Toxicity and human health risk of hair dyes Food and Chemical Toxicology 42 2004 517 543
2. J. Farrell, C. Jenkinson, S.N. Lavergne, J.L. Maggs, B.K. Park, and D.J. Naisbitt Investigation of the immunogenicity of p-phenylenediamine and Bandrowski's base in the mouse Toxicology Letters 185 2009 153 159
3. A. Ramírez-Andreo, A. Hernández-Gil, C. Brufau, N. Marín, N. Jiménez, J. Hernández-Gil, J. Tercedor, and C. Soria Allergic contact dermatitis to temporary henna tattoos Actas Dermosifiliográficas 98 2007 91 95
4. M. Akyüz, and Ş. Ata Determination of aromatic amines in hair dye and henna samples by ion-pair extraction and gas chromatography-mass spectrometry Journal of Pharmaceutical and Biomedical Analysis 47 2008 68 80
5. Y. Ikarashi, and M.-A. Kaniwa Determination of p-phenylenediamine and related antioxidants in rubber boots by high performance liquid chromatography. Development of an analytical method for N-(1-methylheptyl)-N′-phenyl-p- phenylenediamine Journal of Health Science 46 2000 467 473
6. A. Stambouli, M.A. Bellimam, N. El Karni, T. Bouayoun, and A. El Bouri Optimization of an analytical method for detecting paraphenylenediamine (PPD) by GC/MS-iontrap in biological liquids Forensic Science International 146S 2004 S87 S92
7. H.M. Pinheiroa, E. Touraudb, and O. Thomasb Aromatic amines from azo dye reduction: status review with emphasis on direct UV spectrophotometric detection in textile industry wastewaters Dyes Pigments 61 2004 121 139
8. H. Tokuda, Y. Kimura, and S. Takano Determination of dye intermediates in oxidative hair dyes by fused-silica capillary gas chromatography Journal of Chromatography A 367 1986 345 356
9. M. Longo, and A. Cavallaro Determination of aromatic amines at trace levels by derivatization with heptafluorobutyric anhydride and gas chromatography-electron-capture negative-ion chemical ionization mass spectrometry Journal of Chromatography A 753 1996 91 100
10. R.J. Turesky, J.P. Freeman, R.D. Holland, D.M. Nestorick, D.W. Miller, D.L. Ratnasinghe, and F.F. Kadlubar Identification of aminobiphenyl derivatives in commercial hair dyes Chemical Research in Toxicology 16 2003 1162 1173
11. M.L.D. Gioia, A. Leggio, A.L. Pera, A. Liguori, A. Napoli, F. Perri, and C. Siciliano Determination by gas chromatography/mass spectrometry of p-phenylenediamine in hair dyes after conversion to an imine derivative Journal of Chromatography A 1066 2005 143 148
12. P.G. Wang, and A.J. Krynitsky Rapid determination of para- phenylenediamine by gas chromatography-mass spectrometry with selected ion monitoring in henna-containing cosmetic products Journal of Chromatography B 879 2011 1795 1801
13. C. Scarpi, F. Ninci, M. Centini, and C. Anselmi High-performance liquid chromatography determination of direct and temporary dyes in natural hair colourings Journal of Chromatography A 796 1998 319 325
14. J. Zhou, H. Xu, G.-H. Wan, C.-F. Duan, and H. Cui Enhancing and inhibiting effects of aromatic compounds on luminal-dimethylsulfoxide-OH- chemiluminescence and determination of intermediates in oxidative hair dyes by HPLC with chemiluminescence detection Talanta 64 2004 467 477
15. L.-H. Wang, and S.-J. Tsai Simultaneous determination of oxidative hair dye p-phenylenediamine and its metabolites in human and rabbit biological fluids Analytical Biochemistry 312 2003 201 207
16. S.-P. Wang, and T.-H. Huang Separation and determination of aminophenols and phenylenediamines by liquid chromatography and micellar electrokinetic capillary chromatography Analytica Chimica Acta 534 2005 207 214
17. S. Fanali Host-guest complexation in capillary isotachophoresis: II. Determination of aminophenol and diaminobenzene isomers in permanent hair colorants by using capillary isotachophoresis Journal of Chromatography A 470 1989 123 129
18. S. Dong, L. Chi, Z. Yang, P. He, Q. Wang, and Y. Fang Simultaneous determination of dihydroxybenzene and phenylenediamine positional isomers using capillary zone electrophoresis coupled with amperometric detection Journal of Separation Science 32 2009 3232 3238
19. C. Sainthorant, Ph Morin, M. Dreux, A. Baudry, and N. Goetz Separation of phenylenediamine, phenol and aminophenol derivatives by micellar electrokinetic chromatography. Comparison of the role of anionic and cationic surfactants Journal of Chromatography A 717 1995 167 179
20. C.-E. Lin, Y.-T. Chen, and T.-Z. Wang Separation of benzenediamines, benzenediols and aminophenols in oxidative hair dyes by micellar electrokinetic chromatography using cationic surfactants Journal of Chromatography A 837 1999 241 252
21. Y. Zhang, Z. He, and G. Li A novel fluorescent vesicular sensor for saccharides based on boronic acid-diol interaction Talanta 81 2010 591 596
22. S.-Y. Xu, Y.-B. Ruan, X.-X. Luo, Y.-F. Gao, J.-S. Zhao, J.-S. Shen, and Y.-B. Jiang Enhanced saccharide sensing based on simple phenylboronic acid receptor by coupling to Suzuki homocoupling reaction Chemical Communications 46 2010 5864 5866
23. R. Nishiyabu, Y. Kubo, T.D. James, and J.S. Fossey Boronic acid building blocks: tools for sensing and separation Chemical Communications 47 2012 1106 1123
24. Z. Guo, I. Shin, and J. Yoon Recognition and sensing of various species using boronic acid derivatives Chemical Communications 48 2012 5956 5967
25. K. Mulla, P. Dongare, N. Zhou, G. Chen, D.W. Thompson, and Y. Zhao Highly sensitive detection of saccharides under physiological conditions with click synthesized boronic acid-oligomer fluorophores Organic and Biomolecular Chemistry 9 2011 1332 1336
26. G. Springsteen, and B. Wang Alizarin Red S. as a general optical reporter for studying the binding of boronic acids with carbohydrate Chemical Communications 2001 1608 1609
27. S. Arimori, C.J. Ward, and T.D. James A d-glucose selective fluorescent assay Tetrahedron Letters 43 2002 303 305
28. W.M.J. Ma, M.P.P. Morais, F. D'Hooge, J.M.H. van den Elsen, J.P.L. Cox, T.D. James, and J.S. Fossey Dye displacement assay for saccharide detection with boronate hydrogels Chemical Communications 2009 532 534
29. R.W. Layer The chemistry of imines Chemical Reviews 63 1963 489 510
30. V. Saggiomo, and U. Lüning On the formation of imines in water - a comparison Tetrahedron Letters 50 2009 4663 4665
31. M. Jamkratoke, G. Tumcharern, T. Tuntulani, and B. Tomapanaget A selective spectrofluorometric determination of micromolar level of cyanide in water using naphthoquinone imidazole boronic-based sensors and a surfactant cationic CTAB micellar system Journal of Fluorescence 21 2011 1179 1187
32. T. Noipa, S. Srijaranai, T. Tuntulani, and W. Ngeontae New approach for evaluation of the antioxidant capacity based on scavenging DPPH free radical in micelle systems Food Research International 44 2011 798 806
33. K. Ngamdee, T. Noipa, S. Martwiset, T. Tuntulani, and W. Ngeontae Enhancement of sensitivity of glucose sensors from alizarin-boronic acid adductsin aqueous micelles Sensors and Actuators B - Chemical 160 2011 129 138
34. D. Attwood, and A.T. Florence Surfactant Systems 1983 Chapman and Hall London
35. A. Albert, and E.P. Serjeant The Determination of Ionization Constants 1984 Chapman and Hall London
36. J. Yan, G. Springsteen, S. Deeter, and B. Wang The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols - it is not as simple as it appears Tetrahedron 60 2004 11205 11209
37. G. Springsteen, and B. Wang A detailed examination of boronic acid-diol complexation Tetrahedron 58 2002 5291 5300
38. D. Christodouleas, C. Fotakis, K. Papadopoulos, E. Yannakopoulou, and A.C. Calokrinos Development and validation of a chemiluminogenic method for the evaluation of antioxidant activity of hydrophilic and hydrophobic antioxidants Analytica Chimica Acta 652 2009 295 302