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Peroxyoxalate Chemiluminescence for Miniaturized Analytical Flow Systems

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Peroxyoxalate Chemiluminescence for Miniaturized Analytical Flow Systems Peroxyoxalate Chemiluminescence for Miniaturized Analytical Flow Systems by Tobias Jonsson AKADEMISK AVHANDLING som med vederbörligt tillstånd av Rektorsämbetet vid Umeå Universitet för erhållandet av filosofie doktorsexamen framlägges till offentlig granskning vid Kemiska Institutionen, Sal KB3B1 (Stora hörsalen) KBC-huset, Fredagen den 24 Januari 2003, Klockan 13:00. Fakultetsopponent: Professor John W. Birks, Department of Chemistry and Biochemistry, and Cooperative Institute for Research in the Environmental Sciences (CIRES), University of Colorado, Boulder, Colorado, USA. - i - Title: Peroxyoxalate Chemiluminescence for Miniaturized Analytical Flow Systems Author: Tobias Jonsson Department of Chemistry, Umeå University, S-901 87 Umeå, Sweden Abstract: This thesis deals with the peroxyoxalate chemiluminescence (POCL) reaction and its application as a detection technique in flow systems for chemical analysis. Particularly, miniaturized flow systems aimed for separation of molecules. In such systems, a high light intensity and a rapid development of the emission are the desired reaction characteristics, for reasons discussed in this text. The work tries to develop an understanding of the chemical processes involved in POCL, with special emphasis to the species favoring or hindering a rapid light evolution. Hence, is the focus placed on the nature of catalysis and the desired properties of substances acting as catalysts in this reaction. Consequently, the scientific papers on which this work is founded includes both systematic stopped-flow studies of catalyst candidates and of the causes for diminished light emission. In addition, multivariate strategies for reaction optimization in practical analysis situations are treated, and the application of the POCL technique to detection of serum-extracted neuroactive steroids, derivatized with fluorescent moieties, is presented. From the experiments in this thesis it is clear nucleophilic catalysts are the most efficient enhancing compounds, which means that they must possess a carefully balanced characteristics of nucleophilicity, leaving group ability, and basicity. The investigations also conclude that the feature of basicity efficiently can be delegated to a non-nucleophilic co-catalyst, which allow the use of nucleophilic catalysts that need to be deprotonated to be active. This thesis also shows the importance of minimizing the amount of competing nucleophiles at the site of reaction to maintain the emission. This implies that also solvents and buffer substances should be carefully chosen not to interfere with the emission process. The most promising combination of catalysts found in this work was 4,5- dichloroimidazole together with 1,2,2,6,6-pentamethylpiperidne. This arrangement was capable of speeding the reaction more than tenfold while increasing the maximum emission intensity by about the same factor. Keywords: peroxyoxalate, chemiluminescence, nucleophilic catalysis, non-nucleophilic base, imidazole, triazole, aminopyridine, miniaturized, flow system, capillary electrophoresis, multivariate ISBN: 91-7305-377-5 © Copyright, Tobias Jonsson, 2002. All rights reserved. Printed by Solfjädern Offset, Umeå. - ii - This thesis is partly based on the investigations presented in the following papers and manuscripts, that are hereafter referred to by their Roman numerals: I. Determination of C-21 Ketosteroids in Serum Using Trifluoromethanesulfonic Acid Catalyzed Precolumn Dansylation and 1,1’-Oxalyldiimidazole Postcolumn Peroxyoxalate Chemiluminescence Detection Patrik Appelblad, Tobias Jonsson, Torbjörn Bäckström, Knut Irgum Analytical Chemistry, 70 (1998) 5002-5009 II. Heterocyclic Compounds as Catalysts in the Peroxyoxalate Chemiluminescence Reaction of bis(2,4,6-Trichlorophenyl)Oxalate Tobias Jonsson, Malin Emteborg (b. Stigbrand), Knut Irgum Analytica Chimica Acta, 361 (1998) 205-215 III. Very Fast Peroxyoxalate Chemiluminescence Tobias Jonsson, Knut Irgum Analytica Chimica Acta, 400 (1999) 257–264 IV. New Nucleophilic Catalysts for Bright and Fast Peroxyoxalate Chemiluminescence Tobias Jonsson, Knut Irgum Analytical Chemistry, 72 (2000) 1373-1380 V. Preliminary Kinetic Evaluation of Co-Catalyzed Acidic Azoles for Peroxyoxalate Chemiluminescence Detection in Miniaturized Flow Systems Tobias Jonsson manuscript Papers I and IV are reprinted from Analytical Chemistry with permission from the American Chemical Society (copyright 1998 and 2000, respectively), whereas papers II and III are reprinted from Analytica Chimica Acta with permission from Elsevier Science (copyright 1998 and 1999, respectively). - iii - Also by the author but not included in the thesis: A. Mechanism and Applications of Peroxyoxalate Chemiluminescence Malin Stigbrand, Tobias Jonsson, Einar Pontén, Knut Irgum, Richard Bos in A.M. García-Campaña, W.R.G. Baeyens (Eds), ‘Chemiluminescence in Analytical Chemistry’, Marcel Dekker, New York, 2001, Chapter 7, Pages 141-173. B. Noise Characteristics and Analytical Precision of a Direct Injection High Efficiency and Micro Concentric Nebuliser for Sample Introduction in Inductively Coupled Plasma Mass Spectrometry Erik Björn, Tobias Jonsson, Daniel Goitom Journal of Analytical Atomic Spectrometry, 17 (2002) 1257-1263 C. The Origin of Peristaltic Pump Interference Noise Harmonics in Inductively Coupled Plasma Mass Spectrometry Erik Björn, Tobias Jonsson, Daniel Goitom Journal of Analytical Atomic Spectrometry, 17 (2002) 1390-1393 D. Characteristics of Vortexes Formed in Radial Entrance Fountain Detection Cells and their Impact on Chemiluminescence Analysis Tobias Jonsson, Knut Irgum manuscript in preparation for Analytical Chemistry - iv - Table of Contents 1. Introduction................................................................................................................1 2. Peroxyoxalate Chemiluminescence...........................................................................2 2.1 Emission Characteristics.......................................................................................... 3 2.2 Oxalic Reagents........................................................................................................ 5 2.3 Light Generating Reaction....................................................................................... 7 2.3.1 The Overall Reaction ......................................................................................... 7 2.3.2 The High-Energy Intermediate.......................................................................... 7 2.3.3 The Fluorophore Excitation ............................................................................. 11 2.4 Catalysis.................................................................................................................. 13 2.4.1 General-Base Catalysis .................................................................................... 13 2.4.2 Nucleophilic Catalysis...................................................................................... 14 2.4.3 Other Enhancers .............................................................................................. 15 2.5 Side Reactions ........................................................................................................ 16 2.5.1 Hydrolysis ........................................................................................................ 16 2.5.2 Nucleophilic Deactivation................................................................................ 17 2.5.3 Base-Catalyzed Decomposition........................................................................ 17 2.5.4 Emissive Reactions and Miscellaneous............................................................. 18 2.6 Comprehensive Mechanism.................................................................................. 19 3. Chemiluminescence in Analytical Flow Systems....................................................21 3.1 Typical Applications .............................................................................................. 21 3.2 Conventional Systems ........................................................................................... 22 3.3 Miniaturization...................................................................................................... 23 3.3.1 Reaction Kinetics.............................................................................................. 24 3.3.2 Mixing and Instrumentation ........................................................................... 25 3.4 Optimization.......................................................................................................... 27 4. Conclusions and Future Perspectives......................................................................28 5. Acknowledgement.....................................................................................................30 6. References..................................................................................................................32 - v - - vi - Let there be light: and there was light The above words have been claimed to initiate the development of the universe1 and also the birth of rock’n’roll music,2 but more important in the context of this thesis, is that those words capture the very essence of chemiluminescence; to produce light at will.☺ Technically speaking, chemiluminescence is defined as the production of electromagnetic radiation, i.e., photons, with energies ranging from the ultra-violet to the infra-red region of the spectrum, when an electron in an atom or molecule,
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