Fundamental Studies on Poly(2-oxazoline) Side Chain Isomers Using Tandem Mass Spectrometry and Ion Mobility-Mass Spectrometry

Haler, Jean; de la Rosa, Victor R.; Massonnet, Philippe; Far, Johann; Hoogenboom, Richard; De Pauw, Edwin

doi:10.1007/s13361-019-02173-y

Article (Scientific journals)

Fundamental Studies on Poly(2-oxazoline) Side Chain Isomers Using Tandem Mass Spectrometry and Ion Mobility-Mass Spectrometry

Haler, Jean; de la Rosa, Victor R.; Massonnet, Philippe et al.

2019 • In Journal of the American Society for Mass Spectrometry

Peer Reviewed verified by ORBi

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https://hdl.handle.net/2268/234258

DOI
10.1007/s13361-019-02173-y

PubMed
30949970

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Keywords :

Poly(2-oxazoline)s; Synthetic polymer isomers; Tandem mass spectrometry MS/MS; Collision-induced dissociation; Ion mobility-mass spectrometry

Abstract :

[en] When polymer mixtures become increasingly complex, the conventional analysis techniques become insufficient for complete characterization. Mass spectrometric techniques can satisfy this increasing demand for detailed sample characterization. Even though isobaric polymers are indistinguishable using simple mass spectrometry (MS) analyses, more advanced techniques such as tandem MS (MS/MS) or ion mobility (IM) can be used. Here, we report proof of concept for characterizing isomeric polymers, namely poly(2-n-propyl-2-oxazoline) (Pn-PrOx) and poly(2-isopropyl-2-oxazoline) (Pi-PrOx), using MS/MS and IM-MS. Pi-PrOx ions lose in intensity at higher accelerating voltages than Pn-PrOx ions during collision-induced dissociation (CID) MS/MS experiments. A Pn/i-PrOx mixture could also be titrated using survival yield calculations of either precursor ions or cation ejection species. IM-MS yielded shape differences in the degree of polymerization (DP) regions showing the structural rearrangements. Combined MS techniques are thus able to identify and deconvolute the molar mass distributions of the two isomers in a mixture. Finally, the MS/MS and IM-MS behaviors are compared for interpretation.

Research Center/Unit :

MolSys - Molecular Systems - ULiège

Disciplines :

Chemistry

Author, co-author :

Haler, Jean ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique inorganique

de la Rosa, Victor R.; Ghent University > Supramolecular Chemistry Group

Massonnet, Philippe ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique inorganique

Far, Johann ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique inorganique

Hoogenboom, Richard; Ghent University > Supramolecular Chemistry Group

De Pauw, Edwin ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie analytique inorganique

Language :

English

Title :

Fundamental Studies on Poly(2-oxazoline) Side Chain Isomers Using Tandem Mass Spectrometry and Ion Mobility-Mass Spectrometry

Publication date :

2019

Journal title :

Journal of the American Society for Mass Spectrometry

ISSN :

1044-0305

eISSN :

1879-1123

Publisher :

Springer, New-York, United States - New York

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://link.springer.com/article/10.1007/s13361-019-02173-y

Funders :

FRIA - Fonds pour la Formation à la Recherche dans l'Industrie et dans l'Agriculture
FWO - Fonds Wetenschappelijk Onderzoek Vlaanderen
UGent - Universiteit Gent

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since 08 April 2019

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Bibliography

Young, R.J., Lovell, P.A.: Introduction to Polymers. CRC PRESS (2011)
Jeanne Dit Fouque, D., Maroto, A., Memboeuf, A.: Purification and quantification of an isomeric compound in a mixture by collisional excitation in multistage mass spectrometry experiments. Anal. Chem. 88, 10821–10825 (2016)
Josse, T., De Winter, J., Dubois, P., Coulembier, O., Gerbaux, P., Memboeuf, A.: A tandem mass spectrometry-based method to assess the architectural purity of synthetic polymers: a case of a cyclic polylactide obtained by click chemistry. Polym. Chem. 6, 64–69 (2015)
Nasioudis, A., Memboeuf, A., Heeren, R.M.A., Smith, D.F., Vékey, K., Drahos, L., Van Den Brink, O.F.: Discrimination of polymers by using their characteristic collision energy in tandem mass spectrometry. Anal. Chem. 82, 9350–9356 (2010)
Li, X., Chan, Y.T., Newkome, G.R., Wesdemiotis, C.: Gradient tandem mass spectrometry interfaced with ion mobility separation for the characterization of supramolecular architectures. Anal. Chem. 83, 1284–1290 (2011)
Yol, A.M., Dabney, D.E., Wang, S.F., Laurent, B.A., Foster, M.D., Quirk, R.P., Grayson, S.M., Wesdemiotis, C.: Differentiation of linear and cyclic polymer architectures by MALDI tandem mass spectrometry (MALDI-MS2). J. Am. Soc. Mass Spectrom. 24, 74–82 (2013)
Memboeuf, A., Jullien, L., Lartia, R., Brasme, B., Gimbert, Y.: Tandem mass spectrometric analysis of a mixture of isobars using the survival yield technique. J. Am. Soc. Mass Spectrom. 22, 1744–1752 (2011)
Gies, A.P., Kliman, M., McLean, J.A., Hercules, D.M.: Characterization of branching in aramid polymers studied by MALDI-ion mobility/mass spectrometry. Macromolecules. 41, 8299–8301 (2008)
Bagal, D., Zhang, H., Schnier, P.D.: Gas-phase proton-transfer chemistry coupled with TOF mass spectrometry and ion mobility-MS for the facile analysis of poly(ethylene glycols) and PEGylated polypeptide conjugates. Anal. Chem. 80, 2408–2418 (2008)
Trimpin, S., Clemmer, D.E.: Ion mobility spectrometry/mass spectrometry snapshots for assessing the molecular compositions of complex polymeric systems. Anal. Chem. 80, 9073–9083 (2008)
Hoskins, J.N., Trimpin, S., Grayson, S.M.: Architectural differentiation of linear and cyclic polymeric isomers by ion mobility spectrometry-mass spectrometry. Macromolecules. 44, 6915–6918 (2011)
Morsa, D., Defize, T., Dehareng, D., Jérôme, C., De Pauw, E.: Polymer topology revealed by ion mobility coupled with mass spectrometry. Anal. Chem. 86, 9693–9700 (2014)
Foley, C.D., Zhang, B., Alb, A.M., Trimpin, S., Grayson, S.M.: Use of ion mobility spectrometry-mass spectrometry to elucidate architectural dispersity within star polymers. ACS Macro Lett. 4, 778–782 (2015)
Haler, J.R.N., Far, J., Aqil, A., Claereboudt, J., Tomczyk, N., Giles, K., Jérôme, C., De Pauw, E.: Multiple gas-phase conformations of a synthetic linear poly(acrylamide) polymer observed using ion mobility-mass spectrometry. J. Am. Soc. Mass Spectrom. 28, 2492–2499 (2017)
Haler, J.R.N., Massonnet, P., Chirot, F., Kune, C., Comby-Zerbino, C., Jordens, J., Honing, M., Mengerink, Y., Far, J., Dugourd, P., De Pauw, E.: Comparison of different ion mobility setups using poly (ethylene oxide) PEO polymers: drift tube, TIMS, and T-Wave. J. Am. Soc. Mass Spectrom. 29, 114–120 (2018)
Farenc, M., Witt, M., Craven, K., Barrère-Mangote, C., Afonso, C., Giusti, P.: Characterization of polyolefin pyrolysis species produced under ambient conditions by Fourier transform ion cyclotron resonance mass spectrometry and ion mobility-mass spectrometry. J. Am. Soc. Mass Spectrom. 28, 507–514 (2017)
Barrère, C., Selmi, W., Hubert-Roux, M., Coupin, T., Assumani, B., Afonso, C., Giusti, P.: Rapid analysis of polyester and polyethylene blends by ion mobility-mass spectrometry. Polym. Chem. 5, 3576–3582 (2014)
Liu, X., Cool, L.R., Lin, K., Kasko, A.M., Wesdemiotis, C.: Tandem mass spectrometry and ion mobility mass spectrometry for the analysis of molecular sequence and architecture of hyperbranched glycopolymers. Analyst. 140, 1182–1191 (2015)
Hilton, G.R., Jackson, A.T., Thalassinos, K., Scrivens, J.H.: Structural analysis of synthetic polymer mixtures using ion mobility and tandem mass spectrometry. Anal. Chem. 80, 9720–9725 (2008)
Shi, C., Gerişlioğlu, S., Wesdemiotis, C.: Ultrahigh performance liquid chromatography interfaced with mass spectrometry and orthogonal ion mobility separation for the microstructure characterization of amphiphilic block copolymers. Chromatographia. 79, 961–969 (2016)
Hoogenboom, R.: 50 years of poly(2-oxazoline)s. Eur. Polym. J. 88, 448–450 (2017)
Viegas, T.X., Fang, Z., Yoon, K., Weimer, R., Dizman, B.: 6 - Poly(oxazolines) A2 - Parambath, Anilkumar. In: Engineering of Biomaterials for Drug Delivery Systems, pp. 173–198. Woodhead Publishing (2018)
Altuntaş, E., Kempe, K., Crecelius, A., Hoogenboom, R., Schubert, U.S.: ESI-MS & MS/MS analysis of poly(2-oxazoline)s with different side groups. Macromol. Chem. Phys. 211, 2312–2322 (2010)
Altuntaş, E., Weber, C., Kempe, K., Schubert, U.S.: Comparison of ESI, APCI and MALDI for the (tandem) mass analysis of poly(2-ethyl-2-oxazoline)s with various end-groups. Eur. Polym. J. 49, 2172–2185 (2013)
Baumgaertel, A., Weber, C., Knop, K., Crecelius, A., Schubert, U.S.: Characterization of different poly(2-ethyl-2-oxazoline)s via matrix-assisted laser desorption/ionization time-of-flight tandem mass spectrometry. Rapid Commun. Mass Spectrom. 23, 756–762 (2009)
Baumgaertel, A., Weber, C., Fritz, N., Festag, G., Altuntaş, E., Kempe, K., Hoogenboom, R., Schubert, U.S.: Characterization of poly(2-oxazoline) homo- and copolymers by liquid chromatography at critical conditions. J. Chromatogr. A. 1218, 8370–8378 (2011)
Chojnacka, A., Kempe, K., van de Ven, H.C., Englert, C., Hoogenboom, R., Schubert, U.S., Janssen, H.-G., Schoenmakers, P.: Molar mass, chemical-composition, and functionality-type distributions of poly(2-oxazoline)s revealed by a variety of separation techniques. J. Chromatogr. A. 1265, 123–132 (2012)
Biri, B., Nagy, L., Kuki, Á., Tőke Enikő, R., Deák, G., Zsuga, M., Kéki, S.: Collision-induced dissociation study of poly(2-ethyl-2-oxazoline) using survival yields and breakdown curves. J. Mass Spectrom. 48, 16–23 (2012)
Sahn, M., Bandelli, D., Dirauf, M., Weber, C., Schubert Ulrich, S.: Bifunctional initiators as tools to track chain transfer during the CROP of 2-Oxazolines. Macromol. Rapid Commun. 38, 1700396 (2017)
Atılkan, N., Nur, Y., Hacaloglu, J., Schlaad, H.: Direct insertion mass spectrometric analysis of thermal degradation of poly(2-alkyl-2-oxazoline). Macromol. Chem. Phys. 213, 945–951 (2012)
Verbraeken, B., Lava, K., Hoogenboom, R.: Poly(2-oxazoline)s. In: Encyclopedia of Polymer Science and Technology, pp. 1–51. John Wiley & Sons, Inc., Hoboken, NJ, USA (2014)
Hoogenboom, R.: Poly(2-oxazoline)s: a polymer class with numerous potential applications. Angew. Chemie - Int. Ed. 48, 7978–7994 (2009)
de la Rosa, V.R., Tempelaar, S., Dubois, P., Hoogenboom, R., Mespouille, L.: Poly(2-ethyl-2-oxazoline)-block-polycarbonate block copolymers: from improved end-group control in poly(2-oxazoline)s to chain extension with aliphatic polycarbonate through a fully metal-free ring-opening polymerisation process. Polym. Chem. 7, 1559–1568 (2016)
Ruotolo, B.T., Benesch, J.L.P., Sandercock, A.M., Hyung, S.J., Robinson, C.V.: Ion mobility-mass spectrometry analysis of large protein complexes. Nat. Protoc. 3, 1139–1152 (2008)
Giles, K., Williams, J.P., Campuzano, I.: Enhancements in travelling wave ion mobility resolution. Rapid Commun. Mass Spectrom. 25, 1559–1566 (2011)
Altuntas, E., Weber, C., Schubert, U.S.: Detailed characterization of poly(2-ethyl-2oxazoline)s by energy variable collision-induced dissociation study. Rapid Commun. Mass Spectrom. 27, 1095–1100 (2013)
Kuki, Á., Nagy, L., Shemirani, G., Memboeuf, A., Drahos, L., Vékey, K., Zsuga, M., Kéki, S.: A simple method to estimate relative stabilities of polyethers cationized by alkali metal ions. Rapid Commun. Mass Spectrom. 26, 304–308 (2012)
Memboeuf, A., Nasioudis, A., Indelicato, S., Pollreisz, F., Kuki, Á., Kéki, S., Van Den Brink, O.F., Vékey, K., Drahos, L.: Size effect on fragmentation in tandem mass spectrometry. Anal. Chem. 82, 2294–2302 (2010)
Baumgaertel, A., Altuntaş, E., Kempe, K., Crecelius, A., Schubert, U.S.: Characterization of different poly(2-oxazoline) block copolymers by MALDI-TOF MS/MS and ESI-Q-TOF MS/MS. J. Polym. Sci. Part A Polym. Chem. 48, 5533–5540 (2010)
Kuki, Á., Nagy, L., Memboeuf, A., Drahos, L., Vékey, K., Zsuga, M., Kéki, S.: Energy-dependent collision-induced dissociation of lithiated polytetrahydrofuran: effect of the size on the fragmentation properties. J. Am. Soc. Mass Spectrom. 21, 1753–1761 (2010)
Haler, J.R.N., Massonnet, P., Far, J., de la Rosa, V.R., Lecomte, P., Hoogenboom, R., Jérôme, C., De Pauw, E.: Gas-phase dynamics of collision induced unfolding, collision induced dissociation, and electron transfer dissociation-activated polymer ions. J. Am. Soc. Mass Spectrom. 1–10 (2018)
Larriba, C., Fernandez De La Mora, J.: The gas phase structure of coulombically stretched polyethylene glycol ions. J. Phys. Chem. B. 116, 593–598 (2012)
De Winter, J., Lemaur, V., Ballivian, R., Chirot, F., Coulembier, O., Antoine, R., Lemoine, J., Cornil, J., Dubois, P., Dugourd, P., Gerbaux, P.: Size dependence of the folding of multiply charged sodium cationized polylactides revealed by ion mobility mass spectrometry and molecular modelling. Chem. - A Eur. J. 17, 9738–9745 (2011)
Haler, J.R.N., Morsa, D., Lecomte, P., Jérôme, C., Far, J., De Pauw, E.: Predicting ion mobility-mass spectrometry trends of polymers using the concept of apparent densities. Methods. 144, 125–133 (2018)
Trimpin, S., Plasencia, M., Isailovic, D., Clemmer, D.E.: Resolving oligomers from fully grown polymers with IMS-MS. Anal. Chem. 79, 7965–7974 (2007)
Kune, C., Far, J., De Pauw, E.: Accurate drift time determination by traveling wave ion mobility spectrometry: the concept of the diffusion calibration. Anal. Chem. 88, 11639–11646 (2016)
Goossens, H., Catak, S., Glassner, M., de la Rosa, V.R., Monnery, B.D., De Proft, F., Van Speybroeck, V., Hoogenboom, R.: Cationic ring-opening polymerization of 2-propyl-2-oxazolines: understanding structural effects on polymerization behavior based on molecular modeling. ACS Macro Lett. 2, 651–654 (2013)
Shemirani, G., Kéki, S.: Collision Induced Dissociation Study of Polyethers, (2015)