同轴式电化学电喷雾质谱离子源研究蒽电化学衍生十二胺

doi:10.3866/PKU.WHXB201208133

Abstract

Abstract:

In the present study, a coaxial probe was used for online electrochemistry/electrospray mass spectrometry (EC/ES-MS). The probe can be constructed quickly using readily available materials at low cost. A wireless potentiostat floating at the electrospray high voltage was used to control the probe in a two-electrode configuration. Using an acetonitrile solution containing diphenylanthracene or triethylamine, we examined the performances of the probe, including the accuracy of potential control, the conversion efficiency, the response time, and the tolerance to fouling. A silver(I) salt solution (10 mmol·L^-1) in acetonitrile was used as the electrolyte and depolarizer. This decreased the solution resistance of the probe to approximately 250 Ω and enabled precise potential control during online operations. Good correspondence was observed between the hydrodynamic and cyclic voltammograms of diphenylanthracene. At 3.6 μL·min^-1, the response time of the probe was as low as 5 s and the conversion efficiency for triethylamine was 77%. Using the coaxial probe, we investigated the electrochemical derivatization of anthracene with dodecylamine. As a non-polar compound, anthracene usually cannot be detected by ES-MS. However, with the EC/ES-MS, the anthracene was first oxidized electrochemically, and then derivatized online by reactions with dodecylamine. The derivatization produced polar compounds that appeared in the ES-MS in high abundance. The products were identified and the reaction mechanism was elucidated. The results provide insight into the complex electrochemical behavior of anthracene.

Key words: Electrochemistry, Electrospray, Mass spectrometry, Online, Derivatization

MSC2000:

O646

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LING Xing, DING Chuan-Fan. Online Electrochemistry/Electrospray Mass Spectrometry with a Coaxial Probe for Investigation of Electrochemical Derivatization of Anthracene with Dodecylamine[J].Acta Phys. -Chim. Sin., 2012, 28(11): 2616-2624.

References

(1) Crain, P. F. Electrospray Ionization Mass Spectrometry ofNucleic Acids and Their Constituents, In Electrospray Ionization Mass Spectrometry; Cole, R. B. Ed.;Wiley: NewYork, 1997, p 421.
(2) Voyksner, R. D. Combining Liquid Chromatography withElectrospray Mass Spectrometry, In Electrospray Ionization Mass Spectrometry; Cole, R. B. Ed.;Wiley: New York, 1997,p 323.
(3) Severs, J. C.; Smith, R. D. Capillary Electrophoresis:Electrospray Ionization Mass Spectrometry, In Electrospray Ionization Mass Spectrometry; Cole, R. B. Ed.;Wiley: NewYork, 1997, p 343.
(4) Zhou, F. M.; Van Berkel, G. J. Anal. Chem. 1995, 67, 3643. doi: 10.1021/ac00116a005
(5) Xu, X. M.; Lu,W. Z.; Cole, R. B. Anal. Chem. 1996, 68, 4244.doi: 10.1021/ac960362i
(6) Lu,W. Z.; Xu, X. M.; Cole, R. B. Anal. Chem. 1997, 69, 2478.doi: 10.1021/ac9612842
(7) Deng, H. T.; Van Berkel, G. J. Electroanalysis 1999, 11, 857.doi: 10.1002/(SICI)1521-4109(199908)11:12<857::AIDELAN857>3.0.CO;2-1
(8) Diehl, G.; Karst, U. Anal. Bioanal. Chem. 2002, 373, 390. doi: 10.1007/s00216-002-1281-3
(9) Karst, U. Angew. Chem. Int. Edit. 2004, 43, 2476. doi: 10.1002/anie.200301763
(10) Zettersten, C.; Lomoth, R.; Hammarstrom, L.; Sjoberg, P. J. R.;Nyholm, L. J. Electroanal. Chem. 2006, 590, 90. doi: 10.1016/j.jelechem.2006.02.028
(11) Van Berkel, G. J.; Kertesz, V. Anal. Chem. 2007, 79, 5510. doi: 10.1021/ac071944a
(12) Permentier, H. P.; Bruins, A. P.; Bischoff, R. Mini-Rev. Med. Chem. 2008, 8, 46. doi: 10.2174/138955708783331586
(13) Zettersten, C.; Sjoberg, P. J. R.; Nyholm, L. Anal. Chem. 2009,81, 5180. doi: 10.1021/ac802563f
(14) Bond, A. M.; Colton, R.; Dagostino, A.; Downard, A. J.;Traeger, J. C. Anal. Chem. 1995, 67, 1691. doi: 10.1021/ac00106a007
(15) Zhang, T. Y.; Palii, S. P.; Eyler, J. R.; Brajter-Toth, A. Anal. Chem. 2002, 74, 1097. doi: 10.1021/ac015543l
(16) Hayen, H.; Karst, U. Anal. Chem. 2003, 75, 4833. doi: 10.1021/ac0346050
(17) Deng, H. T.; Van Berkel, G. J. Anal. Chem. 1999, 71, 4284.doi: 10.1021/ac990527y
(18) Bokman, C. F.; Zettersten, C.; Sjoberg, P. J. R.; Nyholm, L.Anal. Chem. 2004, 76, 2017. doi: 10.1021/ac030388r
(19) Yoshida, K. Electrooxidation in Organic Chemistry;Wiley: NewYork, 1984.
(20) Friend, K. E.; Ohnesorge,W. E. J. Org. Chem. 1963, 28, 2435.doi: 10.1021/jo01044a502
(21) Majeski, E. J.; Stuart, J. D.; Ohnesorg,W. J. Am. Chem. Soc.1968, 90, 633. doi: 10.1021/ja01005a013
(22) Loveland, J.W.; Dimeler, G. R. Anal. Chem. 1961, 33, 1196.doi: 10.1021/ac60177a022
(23) Smith, P. J.; Mann, C. K. J. Org. Chem. 1969, 34, 1821.doi: 10.1021/jo01258a063
(24) Mann, C. K.; Barnes, K. K. Electrochemical Reactions in Nonaqueous Systems; Marcel Dekker: New York, 1970.
(25) Organic Electrochemistry, 4th ed.; Lund, H., Hammerich, O.Eds.; Marcel Dekker: New York, 2001.
(26) Parker, V. D. Acta Chim. Scand. 1970, 24, 2757. doi: 10.3891/acta.chem.scand.24-2757
(27) Parker, V. D. Acta Chim. Scand. 1970, 24, 3151. doi: 10.3891/acta.chem.scand.24-3151
(28) Parker, V. D. Acta Chim. Scand. 1970, 24, 3162. doi: 10.3891/acta.chem.scand.24-3162
(29) Parker, V. D. Accounts Chem. Res. 1984, 17, 243. doi: 10.1021/ar00103a004
(30) (a) Ling, X.; Ding, C. F. Chin. J. Anal. Chem. 2012, accepted.[凌星, 丁传凡. 分析化学, 2012, 40 (10)]
(b) Ling, X.; Ding, C. F. Coaxial Probe for OnlineElectrochemistry/ Electrospray Mass Spectrometry, InInstrumentation: New Developments in Ionization and Sampling II, Proceedings of the 60th ASMS Conference on MassSpectrometry and Allied Topics, Vancouver, Canada, May20-24, 2012; ASMS: Santa Fe, NM, 2012.
(31) Sioda, R. E. J. Phys. Chem. 1968, 72, 2322. doi: 10.1021/j100853a007
(32) Howell, J. O.;Wightman, R. M. J. Phys. Chem. 1984, 88, 3915.doi: 10.1021/j150662a001
(33) Hammerich, O.; Parker, V. D. Advances in Physical Organic Chemistry 1984, 20, 55. doi: 10.1016/S0065-3160(08)60148-3
(34) Mautjana, N. A.; Estes, J.; Eyler, J. R.; Brajter-Toth, A.Electroanalysis 2008, 20, 1959. doi: 10.1002/elan.v20:18
(35) Yeager, H. L.; Kratochv.B. J. Phys. Chem. 1969, 73, 1963.doi: 10.1021/j100726a053
(36) Bard, A. J.; Faulkner, L. R. Electrochemical Methods; 2nd ed.;Wiley: New York, 2001.
(37) Kertesz, V.; Van Berkel, G. J.; Granger, M. C. Anal. Chem.2005, 77, 4366. doi: 10.1021/ac0503411
(38) Mann, C. K. Anal. Chem. 1964, 36, 2424. doi: 10.1021/ac60219a014
(39) Adenier, A.; Chehimi, M. M.; Gallardo, I.; Pinson, J.; Vila, N.Langmuir 2004, 20, 8243. doi: 10.1021/la049194c
(40) Henderson,W.; McIndoe, J. S. Mass Spectrometry of Inorganic, Coordination, and Organometallic Compounds;Wiley:Chichester, 2005.
(41) Suh, J.; Min, D.W. J. Org. Chem. 1991, 56, 5710. doi: 10.1021/jo00019a048

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Online Electrochemistry/Electrospray Mass Spectrometry with a Coaxial Probe for Investigation of Electrochemical Derivatization of Anthracene with Dodecylamine

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