Tandem mass spectrometry for the analysis of self-sorted pseudorotaxanes: The effects of Coulomb interactions

Journal of Mass Spectrometry

Volumn 45, Issue 7, 2010, Pages 788-798

  Jiang, Wei ^a   Schalley, Christoph A ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Coulomb interaction; Gas phase chemistry; Interlocked molecules; Self sorting; Supramolecular chemistry

Indexed keywords

AMMONIUM COMPOUNDS; COULOMB INTERACTIONS; IONIZATION OF GASES; IONS; MACROMOLECULES; MASS SPECTROMETRY; MOLECULAR PHYSICS; SORTING; STOICHIOMETRY; SUPRAMOLECULAR CHEMISTRY;

AMMONIUM IONS; ANALYTICAL TECHNIQUES; BUILDING BLOCKES; CHARGE REPULSION; CHARGE STATE; CHARGED COMPLEXES; CHARGED IONS; COUNTERIONS; FRAGMENTATION BEHAVIOR; FRAGMENTATION PATTERNS; GAS PHASE CHEMISTRY; GAS-PHASE BEHAVIOR; GASPHASE; INTERLOCKED MOLECULES; NON-COVALENT INTERACTION; PSEUDOROTAXANES; SELF-ASSEMBLED; SELF-SORTING; SOLUTION BEHAVIOR; SOLUTION STRUCTURES; STRUCTURAL INFORMATION; SUPRAMOLECULAR ARCHITECTURES; SUPRAMOLECULAR BOND; SUPRAMOLECULES; TANDEM MASS SPECTROMETRY;

COMPLEXATION;

AMMONIA; ROTAXANE; CROWN ETHER; ION;

ARTICLE; CHEMICAL BOND; CHEMICAL INTERACTION; CONTROLLED STUDY; COVALENT BOND; DRUG STRUCTURE; FRAGMENTATION REACTION; IONIZATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; RELIABILITY; SOLVATION; STOICHIOMETRY; TANDEM MASS SPECTROMETRY; CHEMISTRY; PROCEDURES;

CROWN ETHERS; IONS; ROTAXANES; TANDEM MASS SPECTROMETRY;

EID: 77954440675     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.1769     Document Type: Article

References (46)

1. A. Klug. From macromolecules to biological assemblies. Angewandte Chemie International Edition 1983, 22, 565. DOI: 10.1002/anie.198305653;
2. Angewandte Chemie 1983, 95, 579. DOI: 10.1002/ange.1760950802.
3. F. Diederich, P. J. Stang (Eds). Templated Organic Synthesis. Wiley-VCH: Weinheim/Germany, 2000.
4. G. M. Whitesides, J. P. Mathias, C. T. Seto. Molecular self-assembly and nanochemistry: a chemical strategy for the synthesis of nanostructures. Science 1991, 254, 1312. DOI: 10.1126/science.1962191.
5. J. S. Lindsey. Self-assembly in synthetic routes to molecular devices. Biological principles and chemical perspectives: a review. New Journal of Chemistry 1991, 15, 153.
6. D. Philp, J. F. Stoddart. Self-assembly in natural and unnatural systems. Angewandte Chemie International Edition 1996, 35, 1154. DOI: 10.1002/anie.199611541;
7. AngewandteChemie 1996, 108, 1242. DOI: 10.1002/ange.19961081105.
8. A. Wu, L. Isaacs. Self-sorting: the exception or the rule? Journal of American Chemical Society 2003, 125, 4831. DOI:10.1021/ja028913b.
9. W. Jiang, H. D. F. Winkler, C. A. Schalley. Integrative self-sorting: construction of a cascade-stoppered hetero[3]rotaxane. Journal of American Chemical Society 2008, 130, 13852. DOI: 10.1021/ja806009d.
10. W. Jiang, C. A. Schalley. Integrative self-sorting is a programming language for high level self-assembly. Proceedings of National Academy Sciences of the United States of America 2009, 106, 10425. DOI: 10.1073/pnas.0809512106.
11. C.-J. Zhang, S.-J. Li, J.-Q. Zhang, K.-L. Zhu, N. Li, F.-H. Huang. Bezo-21-crown-7/secondary dialkyammonium salt [2]pseudorotaxane-and [2]rotaxane-type threaded structures. Organic Letters 2007, 9, 5553. DOI: 10.1021/ol702510c.
12. V. Balzani, A. Credi, F. M. Raymo, J. F. Stoddart. Artificial molecular machines. Angewandte Chemie International Edition 2000, 39, 3348. DOI: 10.1002/1521-3773(20001002)39 : 19〈3348::AID-ANIE3348〉 3.0.CO;2-X;
13. AngewandteChemie 2000, 112, 3484. DOI: 10.1002/1521-3757(20001002)112: 19〈3484::AID-ANGE3484〉3.0. CO;2-O.
14. E. R. Kay, D. A. Leigh, F. Zerbetto. Synthetic molecular motors and mechanical machines. Angewandte Chemie International Edition 2007, 46, 72. DOI: 10.1002/anie.200504313;
15. Angewandte Chemie 2007, 119, 72. DOI: 10.1002/ange.200504313.
16. J. B. Fenn. Electrospray wings for molecular elephants. Angewandte Chemie International Edition 2003, 42, 3871. DOI: 10.1002/anie.200300605;
17. Angewandte Chemie 2003, 115, 3999. DOI: 10.1002/ange.200300605.
18. B. Baytekin, H. T. Baytekin, C. A. Schalley. Mass spectrometric studies of non-covalent compounds: why supramolecular chemistry in the gas phase? Organic Biomolecular Chemistry 2006, 4, 2825. DOI: 10.1039/b604265a.
19. H. N. Miras, E. F. Wilson, L. Cronin. Unravelling the complexities of inorganic and supramolecular self-assembly in solution with electrospray and cryospray mass spectrometry. Chemical Communications 2009, 1297. DOI: 10.1039/b819534j.
20. C. A. Schalley, A. Springer. Mass Spectrometry and Gas-Phase Chemistry of Non-Covalent Complexes. Wiley: Hoboken, USA, 2009.
21. W. Jiang, C. A. Schalley. Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties. Beilstein Journal of Organic Chemistry 2010, 6, DOI: 10.3762/bjoc.6.14.
22. W. Jiang, A. Schäfer, P. C. Mohr, C. A. Schalley. Monitoring self-sorting by electrospray ionization mass spectrometry: formation intermediates and error-correction during the self-assembly of multipy threaded pseudorotaxanes. Journal of American Chemical Society 2010, 132, 2309. DOI: 10.1021/ja9101369.
23. K. Vékey. Multiply charged ions. Mass Spectrometry Reviews 1995, 14, 195. DOI: 10.1002/mas.1280140304.
24. D. Schröder, H. Schwarz. Generation, stability, and reactivity of small, multiply charged ions in the gas phase. Journal of Physical Chemistry A 1999, 103, 7385. DOI: 10.1021/jp991332x.
25. A. Dreuw, L. S. Cederbaum. Multiply charged anions in the gas phase. Chemical Reviews 2002, 102, 181. DOI: 10.1021/cr0104227.
26. W. E. Boxford, C. E. H. Dessent. Probing the intrinsic features and environmental stabilization of multiply charged ions. Physical Chemistry Chemical Physics 2006, 8, 5151. DOI: 10.1039/b609123g.
27. R. D. Smith, J. A. Loo, C. J. Barinaga, C. G. Edmonds, H. R. Udseth. Collisional activation and collision-activated dissociation of large multiply charged polypeptides and proteins produced by electrospray ionization. Journal of American Society Mass Spectrometry 1990, 1, 53.
28. D. S. Gross, E. R. Williams. Experimental measurement of Coulomb energy and intrinsic dielectric polarizability of a multiply protonated peptide ion using electrospray ionization Fourier-transform mass spectrometry. Journal of American Chemical Society 1995, 117, 883. DOI: 10.1021/ja00108a004.
29. C. Chanthamontri, J. Liu, S. A. McLuckey, Charge state dependent fragmentation of gaseous alpha-synuclein cations via ion trap and beam-type collisional activation. International Journal of Mass Spectrometry 2009, 283, 9. DOI:10.1016/j.ijms.2008.12.007.
30. R. Grandori. Electrospray-ionization mass spectrometry for protein conformational studies. Current Organic Chemistry 2003, 7, 1589.
31. C. A. Schalley, T. Müller, P. Linnartz, M. Witt, M. Schäfer, A. Lützen. Mass spectrometric characterization and gas-phase chemistry of self-assembling supramolecular squares and triangles. Chemistry - A European Journal 2002, 8, 3538. DOI: 10.1002/1521-3765(20020802)8:15〈3538::AID- CHEM3538〉3.0.CO;2-W.
32. M. Engeser, A. Rang, M. Ferrer, A. Gutierrez, H. T. Baytekin, C. A. Schalley. Reactivity of self-assembled supramolecular complexes in the gas phase: a supramolecular neighbor group effect. International Journal of Mass Spectrometry 2006, 255, 185. DOI:10.1016/j.ijms.2006.01.002.
33. J. Roithová, P. Milko, C. L. Ricketts, D. Schröder, T. Besson, V. Dekoj, M. Bělohradský. Dissociation reactions of free tetrapyridinium tetracations and of their catenanes. Journal of American Chemical Society 2007, 129, 10141. DOI: 10.1021/ja071058h.
34. [6]uril pseudorotaxanes: distinctive gas-phase dissociation and reactivity. Journal of American Chemical Society 2003, 125, 9284. DOI: 10.1021/ja035704y.
35. P. Wang, G. R. Newkome, C. Wesdemiotis. Mass spectrometry analysis of organometallic assemblies: Bis-terpyridine-Ru(II) connectivity. International Journal of Mass Spectrometry 2006, 255, 86. DOI: 10.1016/j.ijms.2006.03.006.
36. M. A. C. Broeren, J. L. J. van Dongen, M. Pittelkow, J. B. Christensen, M. H. P. van Genderen, E. W. Meijer. Multivalency in the gas phase: the study of dendritic aggregates by mass spectrometry. Angewandte Chemie International Edition 2004, 43, 3557. DOI: 10.1002/anie.200453707;
37. AngewandteChemie 2004, 116, 3641. DOI: 10.1002/ange.200453707.
38. R. M. Burke, J. K. Pearce, W. E. Boxford, A. Bruckmann, C. E. H. Dessent. Stabilization of excess charge in isolated adenosine 5′-triphosphate and adenosine 5′-diphosphate multiply and singly charged anions. Journal of Physical Chemistry A 2005, 109, 9775. DOI: 10.1021/jp052937y.
39. J. W. Jones, H. W. Gibson. Ion pairing and host-guest complexation in low dielectric constant solvents. Journal of American Chemical Society 2003, 125, 7001. DOI: 10.1021/ja034442x.
40. A. L. Rochwood, M. Busman, R. D. Smith. Coulombic effects in the dissociation of large highly charged ions. International Journal of Mass Spectrometry and Ion Processes 1991, 111, 103.
41. C. A. Schalley, C. Verhaelen, F.-G. Klärner, U. Hahn, F. Vögtle. Gas-phase host-guest chemistry of dendritic viologens and molecular tweezers: a remarkably strong effect on dication stability. Angewandte Chemie International Edition 2005, 44, 477. DOI: 10.1002/anie.200461872;
42. Angewandte Chemie 2005, 117, 481. DOI: 10.1002/ange.200461872.
43. R. R. Julian, J. A. May, B. M. Stoltz, J. L. Beauchamp. Molecular moustraps: gas-phase studies of the covalent coupling of noncovalent complexes initiated by reactive carbenes formed by controlled activation of diazo precursors. Angewandte Chemie International Edition 2003, 42, 1012. DOI: 10.1002/anie.200390258;
44. AngewandteChemie 2003, 115, 1042. DOI: 10.1002/ange.200390233.
45. NIST Chemistry WebBook. NIST Standard Reference Database No. 69, P. J. Linstrom, W. G. Mallard (Eds). National Institute of Standards and Technology:Gaithersburg, MD, 20899, http://webbook.nist.gov (retrieved August 17, 2009).
46. E. P. Hunter, S. G. Lias. Evaluated gas phase basicities and proton affinities of molecules: an update. Journal of Physical and Chemical Reference Data 1998, 27, 413. DOI:10.1063/1.556018.