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The Gas-Phase Chemistry of Novel Carbon-Rich Molecules

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The Gas-Phase Chemistry of Novel Carbon-Rich Molecules The Gas-Phase Chemistry of Novel Carbon-Rich Molecules An Investigation by Means of Modern Mass Spectrometry ✵ Die Gasphasenchemie von Neuartigen Kohlenstoffreichen Molekülen Eine Untersuchung Mittels Moderner Massenspektrometrie Der Naturwissenschaftlichen Fakultät der Friedrich-Alexander-Universität Erlangen-Nürnberg (FAU) zur Erlangung des Doktorgrades Dr. rer. nat. vorgelegt von ROLF W. KIRSCHBAUM aus Nürnberg Als Dissertation genehmigt von der Naturwissenschaftlichen Fakultät der Friedrich-Alexander-Universität Erlangen-Nürnberg Tag der mündlichen Prüfung: 29. April 2016 Vorsitzender des Promotionsorgans: Prof. Dr. Jörn Wilms Gutachter / in: Prof. Dr. Thomas Drewello Prof. Dr. Carola Kryschi Für Gréta. Die vorliegende Arbeit entstand in der Zeit von Oktober 2011 bis September 2015. Mein Dank gilt Prof. Dr. Thomas Drewello, Dr. Marc S. von Gernler, Dr. Jing Li, Dr. Leanne C. Nye, Ina D. Kellner, Thomas S. Neugebauer, Jakob F. Hitzenberger, Prof. Dr. Walter Bauer, Prof. Dr. Andreas Hirsch, Prof. Dr. Rik R. Tykwinski, Dominik Prenzel, Dr. Stephanie Frankenberger, PD Dr. Christoph Böttcher, Dr. Jörg Schönamsgruber, Dr. Boris Schade, Dr. Lennard K. Wasserthal, Chau Vinh, Prof. Dr. Ivana Ivanović-Burmazović, Markus Hausmann, Prof. Dr. Olga V. Boltalina, Prof. Dr. Steven H. Strauss, Dr. Theodor Milek, Dr. Christian Lübbert, Dr. Doris Segets, Prof. Dr. Wolfgang Peukert, Prof. Dr. Dirk Zahn, Dr. Ana-Maria Krestel, Dr. Günter Schmid, Prof. Dr. Dirk M. Guldi, Dr. Florian Kessler, Vera Warmbrunn, Dr. Christian Neiß, Prof. Dr. Andreas Görling, Xenia Kostrov, Dirk Harnisch, Gerd Gätzschmann, Irmgard Ismayer, Margit Hartmann, Beate Maaß, Gertrud Weiß, Martin Kolacyak, Andrea Buchner, Dr. Andreas Bayer, Anette Göbel, Dr. Frank Hauke, Friedhold Wölfel, Thomas Hofmann, Hermann Hauke, Viola Ziegler, Bernd Hofmann, Angelika Leistner, Corinne Wiegner, Dorjkhand Rudolph, Markus Paesler, Florian Warko, Bernd Kreß, Uwe Sauer, Hans-Peter Bäumler, Dr. Georg Brehm, Dr. Guido Sauer, Dr. Karin Mansyreff, Dr. Christain Ehli, Dr. Axel Kahnt, Rauda Träger, Margarete Dziallach, Wolfgang Donaubauer, Dr. Frank Hampel, der Deutschen Forschungsgemeinschaft (DFG) — SFB 953 ‘‘Synthetic Carbon Allotropes’’, der Graduate School Molecular Science (GSMS), Evelyn Abdoulaye, Christian Sprogar, Reinhard Pinzer, Dr. Willy Weiß, Beatrice Baars, Marion Simon, Margit Gotzler, Daniela Schramm, Thomas Loos und meiner Familie. Contents __________________________________________________________________________________ Contents Contents .................................................................................................................................................. i Figures ................................................................................................................................................... iii Abbreviations & Symbols .................................................................................................................... v Introduction ........................................................................................................................................... 1 1 Aims .......................................................................................................................................... 1 2 Gas-Phase Ion Chemistry ....................................................................................................... 1 2.1 Ionisation ........................................................................................................................... 1 2.1.1 Ionisation Energy (IE) .............................................................................................. 1 2.1.2 Electron Affinity (EA) .............................................................................................. 3 2.2 Ion Formation by Cation / Anion-Attachment .............................................................. 3 2.2.1 Gas-Phase Basicity (GB) and Proton Affinity (PA) .............................................. 3 2.2.2 Gas-Phase Acidity (GA) ........................................................................................... 4 2.2.3 Metal Cation Affinities ............................................................................................. 4 3 Experimental Section .............................................................................................................. 6 3.1 Ion Sources ........................................................................................................................ 6 3.1.1 ESI source................................................................................................................... 6 3.1.2 Matrix-Assisted Laser Desorption / Ionisation (MALDI) .................................. 12 3.2 Ion Transfer (In ESI-Instruments) ................................................................................ 22 3.2.1 Glass Capillary ........................................................................................................ 22 3.2.2 Skimmer ................................................................................................................... 23 3.2.3 Ion Funnel ................................................................................................................ 23 3.2.4 RF-only Multipoles ................................................................................................. 24 3.3 Mass Analysers ............................................................................................................... 25 3.3.1 Linear Quadrupole (Q) .......................................................................................... 25 3.3.2 Quadrupole Ion Trap (QIT)................................................................................... 27 3.3.3 Time-of-Flight (TOF) Analyser ............................................................................. 33 i Contents __________________________________________________________________________________ 3.4 Detector ............................................................................................................................ 37 3.4.1 Channel Electron Multiplier (CEM, Channeltron) ............................................. 38 3.4.2 Micro Channel Plate (MCP) .................................................................................. 38 3.5 Isotope Pattern ................................................................................................................ 38 3.6 Resolution & Resolving Power[144] ................................................................................ 39 3.6.1 Resolution: 10 %-Valley Definition ....................................................................... 39 3.6.2 Resolution: Peak Width Definition ...................................................................... 39 3.6.3 Full Width at Half Maximum (FWHM) .............................................................. 39 3.6.4 Resolving Power in Mass Spectrometry .............................................................. 40 3.7 Instruments ...................................................................................................................... 40 3.7.1 BRUKER esquire6000 ................................................................................................ 40 3.7.2 BRUKER micrOTOF-Q II ......................................................................................... 40 3.7.3 BRUKER Reflex IV .................................................................................................... 41 3.7.4 SHIMADZU Axima Confidence .............................................................................. 41 4 Compounds ............................................................................................................................ 42 4.1 Polyynes ........................................................................................................................... 42 4.2 Fullerenes and Fullerene Derivatives .......................................................................... 42 4.3 Perylenetetracarboxylic Acid Diimides (PDIs) ........................................................... 44 4.4 Polycationic [60]Fullerene Hexakis-Adduct ............................................................... 45 4.5 Neutral Transition Metal Complexes (nTMCs) .......................................................... 46 References ............................................................................................................................................ 47 Oral Contributions & Poster Presentations .................................................................................... 57 Papers & Patents ................................................................................................................................. 59 Appendix ............................................................................................................................................. 63 ii Figures __________________________________________________________________________________ Figures Figure 1. Vertical and adiabatic transition in a diatomic molecule ............................................... 2 Figure 2. Scheme of an electrospray ionisation (ESI) ion source ................................................... 6 Figure 3. Different electrospray set-ups ............................................................................................ 7 Figure 4. Scheme of an ESI ion source working as an electrolysis cell ........................................
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