Molecular level differentiation between end‐capped and intramolecular azofunctional oligo(ε‐caprolactone) positional isomers through liquid chromatography multistage mass spectrometry |
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| Authors: | Cristian Peptu Oscar F van den Brink Valeria Harabagiu Bogdan C Simionescu Marek Kowalczuk Jerzy Silberring |
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| Institution: | 1. “Petru Poni” Institute of Macromolecular Chemistry, Aleea Grigore Ghica Voda 41A, 700487, Iasi, Romania;2. Institute of Chemistry and Environmental Protection, “Jan Dlugosz” University of Czestochowa, 13/15 Armii Krajowej Av., 42–200 Czestochowa, Poland;3. AkzoNobel Research, Development & Innovation, P.O. Box 10, 7400 AA, Deventer, The Netherlands;4. TI‐COAST, Science Park 904, 1098 XH, Amsterdam, The Netherlands;5. Department of Natural and Synthetic Polymers, “Gheorghe Asachi” Technical University of Iasi, D. Mangeron 71A, 700050 Iasi, Romania;6. Polish Academy of Sciences, Centre of Polymer and Carbon Materials, 34 M. Sklodowskiej‐Curie, 41‐819 Zabrze, Poland;7. AGH University of Science and Technology, Al. Mickiewicza 30, 30‐059 Kraków, Poland |
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| Abstract: | End‐capped and intramolecular azofunctional oligocaprolactones were characterized at molecular level by liquid chromatography electrospray ionization mass spectrometry (ESI MS) and NMR spectroscopy. The Disperse Red 19 (DR19) azofunctional oligomers, DC, were synthesized by ring‐opening oligomerization of ε‐caprolactone (ε‐CL) initiated by the hydroxyl groups of DR19 azo dye. The reaction products consist of a minor fraction of end‐capped azo functional oligocaprolactone (α‐DC), that is, a single CL arm oligomer, and a major fraction of intramolecular azo functional oligocaprolactone (β‐DC), that is, a two CL arms oligomer. The chromatographic separation was used to discriminate between α‐DC and β‐DC, and the results were confirmed by MS/MS performed on an ESI ion trap instrument. The results supported by accurate mass data obtained for product ions using an ESI quadrupole time of flight instrument demonstrate the qualitative discrimination at the molecular level between intramolecular and end‐capped azofunctional oligoesters isomers through a relatively simple multistage mass spectrometry experiment. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012 |
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| Keywords: | azo polymers oligomers polyesters high performance liquid chromatography (HPLC) mass spectrometry collision‐induced dissociation charge exchange reactions |
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