Assessing the Structural Heterogeneity of Isomeric Homo and Copolymers: an Approach Combining Ion Mobility Mass Spectrometry and Molecular Dynamics Simulations
CIRMAP - Centre d'Innovation et de Recherche en Matériaux Polymères CISMA - Centre Interdisciplinaire de Spectrométrie de Masse
Disciplines :
Chemistry
Author, co-author :
Duez, Quentin ; Université de Mons > Faculté des Sciences > Service de Synthèse et spectrométrie de masse organiques
Moins, Sébastien ; Université de Mons > Faculté des Sciences > Service des Matériaux Polymères et Composites
Coulembier, Olivier ; Université de Mons > Faculté des Sciences > Service des Matériaux Polymères et Composites
De Winter, Julien ; Université de Mons > Faculté des Sciences > Service de Synthèse et spectrométrie de masse organiques
Cornil, Jérôme ; Université de Mons > Faculté des Sciences > Service de Chimie des matériaux nouveaux
Gerbaux, Pascal ; Université de Mons > Faculté des Sciences > Service de Synthèse et spectrométrie de masse organiques
Language :
English
Title :
Assessing the Structural Heterogeneity of Isomeric Homo and Copolymers: an Approach Combining Ion Mobility Mass Spectrometry and Molecular Dynamics Simulations
Publication date :
12 October 2020
Journal title :
Journal of the American Society for Mass Spectrometry
ISSN :
1044-0305
Publisher :
Springer, New-York, United States - New York
Volume :
31
Issue :
11
Pages :
2379-2388
Peer reviewed :
Peer Reviewed verified by ORBi
Research unit :
S816 - Matériaux Polymères et Composites S836 - Synthèse et spectrométrie de masse organiques
Research institute :
R400 - Institut de Recherche en Science et Ingénierie des Matériaux R100 - Institut des Biosciences
Hanton, S. D. Mass spectrometry of polymers and polymer surfaces. Chem. Rev. 2001, 101, 527-569, 10.1021/cr9901081
Montaudo, M. S. Mass spectra of copolymers. Mass Spectrom. Rev. 2002, 21, 108-144, 10.1002/mas.10021
Crecelius, A. C.; Becer, C. R.; Knop, K.; Schubert, U. S. Block Length Determination of the Block Copolymer mPEG-b-PS Using MALDI-TOF MS/MS. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 4375-4384, 10.1002/pola.24223
Weidner, S. M.; Trimpin, S. Mass spectrometry of synthetic polymers. Anal. Chem. 2010, 82, 4811-4829, 10.1021/ac101080n
Crotty, S.; Gerislioglu, S.; Endres, K. J.; Wesdemiotis, C.; Schubert, U. S. Polymer architectures via mass spectrometry and hyphenated techniques: A review. Anal. Chim. Acta 2016, 932, 1-21, 10.1016/j.aca.2016.05.024
Steinkoenig, J.; Cecchini, M. M.; Reale, S.; Goldmann, A. S.; Barner-Kowollik, C. Supercharging Synthetic Polymers: Mass Spectrometric Access to Nonpolar Synthetic Polymers. Macromolecules 2017, 50, 8033-8041, 10.1021/acs.macromol.7b02018
Wesdemiotis, C. Multidimensional Mass Spectrometry of Synthetic Polymers and Advanced Materials. Angew. Chem., Int. Ed. 2017, 56, 1452-1464, 10.1002/anie.201607003
De Bruycker, K.; Welle, A.; Hirth, S.; Blanksby, S. J.; Barner-Kowollik, C. Mass spectrometry as a tool to advance polymer science. Nature Reviews Chemistry 2020, 4, 257-268, 10.1038/s41570-020-0168-1
Charles, L.; Chendo, C.; Poyer, S. Ion Mobility Spectrometry-Mass Spectrometry Coupling for Synthetic Polymers. Rapid Commun. Mass Spectrom. 2020, 34, e8624, 10.1002/rcm.8624
Barner-Kowollik, C.; Falkenhagen, J.; Gruendling, T.; Weidner, S. Mass Spectrometry in Polymer Chemistry; Wiley-VCH Verlag GmbH & Co.: Weinheim, Germany, 2012. 10.1002/9783527641826.ch
Chaicharoen, K.; Polce, M. J.; Singh, A.; Pugh, C.; Wesdemiotis, C. Characterization of linear and branched polyacrylates by tandem mass spectrometry. Anal. Bioanal. Chem. 2008, 392, 595-607, 10.1007/s00216-008-1969-0
Winter, J. D.; Deshayes, G.; Boon, F.; Coulembier, O.; Dubois, P.; Gerbaux, P. MALDI-ToF analysis of polythiophene: use of trans-2-[3-(4-t-butyl-phenyl)-2-methyl-2-propenylidene]malononitrile-DCTB-as matrix. J. Mass Spectrom. 2011, 46, 237-246, 10.1002/jms.1886
Alalwiat, A.; Grieshaber, S. E.; Paik, B. A.; Kiick, K. L.; Jia, X.; Wesdemiotis, C. Top-down mass spectrometry of hybrid materials with hydrophobic peptide and hydrophilic or hydrophobic polymer blocks. Analyst 2015, 140, 7550-7564, 10.1039/C5AN01600B
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. 2015, 6, 64-69, 10.1039/C4PY01087F
Mao, J.; Zhang, B.; Zhang, H.; Elupula, R.; Grayson, S. M.; Wesdemiotis, C. Elucidating Branching Topology and Branch Lengths in Star-Branched Polymers by Tandem Mass Spectrometry. J. Am. Soc. Mass Spectrom. 2019, 30, 1981-1991, 10.1007/s13361-019-02260-0
Wesdemiotis, C.; Solak, N.; Polce, M. J.; Dabney, D. E.; Chaicharoen, K.; Katzenmeyer, B. C. Fragmentation pathways of polymer ions. Mass Spectrom. Rev. 2011, 30, 523-559, 10.1002/mas.20282
Doerr, A.; Finkelstein, J.; Jarchum, I.; Goodman, C.; Dekker, B. Nature Milestones: Mass Spectrometry. Nature Milestones 2015, 5, 1-46, 10.1038/nmeth.3558
Amalian, J.-A.; Cavallo, G.; Al Ouahabi, A.; Lutz, J.-F.; Charles, L. Revealing Data Encrypted in Sequence-Controlled Poly(Alkoxyamine Phosphodiester)s by Combining Ion Mobility with Tandem Mass Spectrometry. Anal. Chem. 2019, 91, 7266-7272, 10.1021/acs.analchem.9b00813
Lee, J. M.; Koo, M. B.; Lee, S. W.; Lee, H.; Kwon, J.; Shim, Y. H.; Kim, S. Y.; Kim, K. T. High-density information storage in an absolutely defined aperiodic sequence of monodisperse copolyester. Nat. Commun. 2020, 11, 1-9, 10.1038/s41467-019-13952-2
Huijser, S.; Staal, B. B. P.; Huang, J.; Duchateau, R.; Koning, C. E. Chemical Composition and Topology of Poly(lactide-co-glycolide) Revealed by Pushing MALDI-TOF MS to Its Limit. Angew. Chem. 2006, 118, 4210-4214, 10.1002/ange.200600594
Huijser, S.; Mooiweer, G. D.; Van Der Hofstad, R.; Staal, B. B. P.; Feenstra, J.; Van Herk, A. M.; Koning, C. E.; Duchateau, R. Reactivity ratios of comonomers from a single MALDI-ToF-MS measurement at one feed composition. Macromolecules 2012, 45, 4500-4510, 10.1021/ma300400d
Altuntaş, E.; Schubert, U. S. "Polymeromics": Mass spectrometry based strategies in polymer science toward complete sequencing approaches: A review. Anal. Chim. Acta 2014, 808, 56-69, 10.1016/j.aca.2013.10.027
Smith, D. P.; Knapman, T. W.; Campuzano, I.; Malham, R. W.; Berryman, J. T.; Radford, S. E.; Ashcroft, A. E. Deciphering drift time measurements from travelling wave ion mobility spectrometry-mass spectrometry studies. Eur. J. Mass Spectrom. 2009, 15, 113-130, 10.1255/ejms.947
Lanucara, F.; Holman, S. W.; Gray, C. J.; Eyers, C. E. The power of ion mobility-mass spectrometry for structural characterization and the study of conformational dynamics. Nat. Chem. 2014, 6, 281-294, 10.1038/nchem.1889
Gabelica, V.; Marklund, E. Fundamentals of Ion Mobility Spectrometry. Curr. Opin. Chem. Biol. 2018, 42, 51-59, 10.1016/j.cbpa.2017.10.022
Gabelica, V.; Shvartsburg, A. A.; Afonso, C.; Barran, P.; Benesch, J. L. P.; Bleiholder, C.; Bowers, M. T.; Bilbao, A.; Bush, M. F.; Campbell, J. L.; Campuzano, I. D. G.; Causon, T.; Clowers, B. H.; Creaser, C. S.; De Pauw, E.; Far, J.; Fernandez-Lima, F.; Fjeldsted, J. C.; Giles, K.; Groessl, M.; Hogan, C. J., Jr.; Hann, S.; Kim, H. I.; Kurulugama, R. T.; May, J. C.; McLean, J. A.; Pagel, K.; Richardson, K.; Ridgeway, M. E.; Rosu, F.; Sobott, F.; Thalassinos, K.; Valentine, S. J.; Wyttenbach, T. Recommendations for reporting ion mobility Mass Spectrometry measurements. Mass Spectrom. Rev. 2019, 38, 291-320, 10.1002/mas.21585
Hoskins, J. N.; Trimpin, S.; Grayson, S. M. Architectural Differentiation of Linear and Cyclic Polymeric Isomers by Ion Mobility Spectrometry-Mass Spectrometry. Macromolecules 2011, 44, 6915-6918, 10.1021/ma2012046
Morsa, D.; Defize, T.; Dehareng, D.; Jerome, C.; De Pauw, E. Polymer topology revealed by ion mobility coupled with mass spectrometry. Anal. Chem. 2014, 86, 9693-9700, 10.1021/ac502246g
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. 2015, 4, 778-782, 10.1021/acsmacrolett.5b00299
Liénard, R.; Duez, Q.; Grayson, S. M.; Gerbaux, P.; Coulembier, O.; De Winter, J. Limitations of ion mobility spectrometry-mass spectrometry for the relative quantification of architectural isomeric polymers: A case study. Rapid Commun. Mass Spectrom. 2020, 34 (S2), e8660, 10.1002/rcm.8660
Austin, C. A.; Inutan, E. D.; Bohrer, B. C.; Li, J.; Fischer, J. L.; Wijerathne, K.; Foley, C. D.; Lietz, C. B.; Woodall, D. W.; Imperial, L. F.; Clemmer, D. E.; Trimpin, S.; Larsen, B. S. Resolving Isomers of Star-Branched Poly(Ethylene Glycols) by IMS-MS using Multiply-Charged Ions. J. Am. Soc. Mass Spectrom. 2020, in press. 10.1021/jasms.0c00045
Baker, E. S.; Gidden, J.; Simonsick, W. J.; Grady, M. C.; Bowers, M. T. Sequence dependent conformations of glycidyl methacrylate/butyl methacrylate copolymers in the gas phase. Int. J. Mass Spectrom. 2004, 238, 279-286, 10.1016/j.ijms.2004.04.020
Shi, S. D.-H.; Hendrickson, C. L.; Marshall, A. G.; Simonsick, W. J.; Aaserud, D. J. Identification, Composition, and Asymmetric Formation Mechanism of Glycidyl Methacrylate/Butyl Methacrylate Copolymers up to 7000 Da from Electrospray Ionization Ultrahigh-Resolution Fourier Transform Ion Cyclotron Resonance Mass Spectrometry. Anal. Chem. 1998, 70, 3220-3226, 10.1021/ac980316d
Jackson, A. T.; Scrivens, J. H.; Williams, J. P.; Baker, E. S.; Gidden, J.; Bowers, M. T. Microstructural and conformational studies of polyether copolymers. Int. J. Mass Spectrom. 2004, 238, 287-297, 10.1016/j.ijms.2004.09.025
Von Helden, G.; Wyttenbach, T.; Bowers, M. T. Conformation of macromolecules in the gas phase: Use of matrix-assisted laser desorption methods in ion chromatography. Science 1995, 267, 1483-1485, 10.1126/science.267.5203.1483
Gidden, J.; Wyttenbach, T.; Batka, J. J.; Weis, P.; Jackson, A. T.; Scrivens, J. H.; Bowers, M. T. Folding energetics and dynamics of macromolecules in the gas phase: Alkali ion-cationized poly(ethylene terephthalate) oligomers. J. Am. Chem. Soc. 1999, 121, 1421-1422, 10.1021/ja9831047
Gidden, J.; Wyttenbach, T.; Jackson, A. T.; Scrivens, J. H.; Bowers, M. T. Gas-Phase Conformations of Synthetic Polymers: Poly(ethylene glycol), Poly(propylene glycol), and Poly(tetramethylene glycol). J. Am. Chem. Soc. 2000, 122, 4692-4699, 10.1021/ja993096+
Ito, K.; Kitagawa, S.; Ohtani, H. Analysis of Multiply Charged Poly (ethylene oxide-co-propylene oxide) Using Electrospray Ionization-Ion Mobility Spectrometry-Mass Spectrometry. Anal. Sci. 2019, 35, 169-174, 10.2116/analsci.18P332
Ude, S.; Fernández De La Mora, J.; Thomson, B. A. Charge-induced unfolding of multiply charged polyethylene glycol ions. J. Am. Chem. Soc. 2004, 126, 12184-12190, 10.1021/ja0381306
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.-Eur. J. 2011, 17, 9738-9745, 10.1002/chem.201100383
Larriba, C.; Fernandez de la Mora, J. The gas phase structure of coulombically stretched polyethylene glycol ions. J. Phys. Chem. B 2012, 116, 593-598, 10.1021/jp2092972
Larriba, C.; Fernandez de la Mora, J.; Clemmer, D. E. Electrospray ionization mechanisms for large polyethylene glycol chains studied through tandem ion mobility spectrometry. J. Am. Soc. Mass Spectrom. 2014, 25, 1332-1345, 10.1007/s13361-014-0885-0
Duez, Q.; Josse, T.; Lemaur, V.; Chirot, F.; Choi, C. M.; Dubois, P.; Dugourd, P.; Cornil, J.; Gerbaux, P.; De Winter, J. Correlation between the shape of the ion mobility signals and the stepwise folding process of polylactide ions. J. Mass Spectrom. 2017, 52, 133-138, 10.1002/jms.3915
Haler, J. R. N.; Far, J.; Aqil, A.; Claereboudt, J.; Tomczyk, N.; Giles, K.; Jerome, 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. 2017, 28, 2492-2499, 10.1007/s13361-017-1769-x
Chen, X.; Raab, S. A.; Poe, T.; Clemmer, D. E.; Larriba-Andaluz, C. Determination of Gas-Phase Ion Structures of Locally Polar Homopolymers Through High-Resolution Ion Mobility Spectrometry-Mass Spectrometry. J. Am. Soc. Mass Spectrom. 2019, 30, 905-918, 10.1007/s13361-019-02184-9
Trimpin, S.; Plasencia, M.; Isailovic, D.; Clemmer, D. E. Resolving oligomers from fully grown polymers with IMS-MS. Anal. Chem. 2007, 79, 7965-7974, 10.1021/ac071575i
Duez, Q.; Metwally, H.; Hoyas, S.; Lemaur, V.; Cornil, J.; De Winter, J.; Konermann, L.; Gerbaux, P. Effects of electrospray mechanisms and structural relaxation on polylactide ion conformations in the gas phase: insights from ion mobility spectrometry and molecular dynamics simulations. Phys. Chem. Chem. Phys. 2020, 22, 4193-4204, 10.1039/C9CP06391A
Nakayama, Y.; Aihara, K.; Cai, Z.; Shiono, T.; Tsutsumi, C. Synthesis and biodegradation of poly(L-lactide-co-β-propiolactone). Int. J. Mol. Sci. 2017, 18, 1312-1321, 10.3390/ijms18061312
Duez, Q.; Chirot, F.; Liénard, R.; Josse, T.; Choi, C. M.; Coulembier, O.; Dugourd, P.; Cornil, J.; Gerbaux, P.; De Winter, J. Polymers for Traveling Wave Ion Mobility Spectrometry Calibration. J. Am. Soc. Mass Spectrom. 2017, 28, 2483-2491, 10.1007/s13361-017-1762-4
Van Der Spoel, D.; Lindahl, E.; Hess, B.; Groenhof, G.; Mark, A. E.; Berendsen, H. J. GROMACS: fast, flexible, and free. J. Comput. Chem. 2005, 26, 1701-1718, 10.1002/jcc.20291
Mayo, S. L.; Olafson, B. D.; Goddard, W. A., III DREIDING: A Generic Force Field for Molecular Simulations. J. Phys. Chem. 1990, 94, 8897-8909, 10.1021/j100389a010
Ewing, S. A.; Donor, M. T.; Wilson, J. W.; Prell, J. S. Collidoscope: An Improved Tool for Computing Collisional Cross-Sections with the Trajectory Method. J. Am. Soc. Mass Spectrom. 2017, 28, 587-596, 10.1007/s13361-017-1594-2
Mezzasalma, L.; Dove, A. P.; Coulembier, O. Organocatalytic ring-opening polymerization of L-lactide in bulk: A long standing challenge. Eur. Polym. J. 2017, 95, 628-634, 10.1016/j.eurpolymj.2017.05.013
Duez, Q.; Liénard, R.; Moins, S.; Lemaur, V.; Coulembier, O.; Cornil, J.; Gerbaux, P.; De Winter, J. One Step Further in the Characterization of Synthetic Polymers by Ion Mobility Mass Spectrometry: Evaluating the Contribution of End-groups. Polymers 2019, 11, 688, 10.3390/polym11040688
Poyer, S.; Comby-Zerbino, C.; Choi, C. M.; MacAleese, L.; Deo, C.; Bogliotti, N.; Xie, J.; Salpin, J. Y.; Dugourd, P.; Chirot, F. Conformational Dynamics in Ion Mobility Data. Anal. Chem. 2017, 89, 4230-4237, 10.1021/acs.analchem.7b00281
Wyttenbach, T.; Von Helden, G.; Bowers, M. T. Conformations of alkali ion cationized polyethers in the gas phase: polyethylene glycol and bis[(benzo-15-crown-5)-15-ylmethyl] pimelate. Int. J. Mass Spectrom. Ion Processes 1997, 165-166, 377-390, 10.1016/S0168-1176(97)00179-1
Sherman, C. L.; Brodbelt, J. S.; Marchand, A. P.; Poola, B. Electrospray ionization mass spectrometric detection of self-assembly of a crown ether complex directed by π-stacking interactions. J. Am. Soc. Mass Spectrom. 2005, 16, 1162-1171, 10.1016/j.jasms.2005.03.014
Bleiholder, C.; Johnson, N. R.; Contreras, S.; Wyttenbach, T.; Bowers, M. T. Molecular Structures and Ion Mobility Cross Sections: Analysis of the Effects of He and N2 Buffer Gas. Anal. Chem. 2015, 87, 7196-7203, 10.1021/acs.analchem.5b01429
Servage, K. A.; Silveira, J. A.; Fort, K. L.; Russell, D. H. Cryogenic Ion Mobility-Mass Spectrometry: Tracking Ion Structure from Solution to the Gas Phase. Acc. Chem. Res. 2016, 49, 1421-1428, 10.1021/acs.accounts.6b00177
