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Investigations Into S-Heptazine-Based Carbon Nitride Precursors

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Investigations Into S-Heptazine-Based Carbon Nitride Precursors Dissertation zur Erlangung des Doktorgrades der Fakultät für Chemie und Pharmazie der Ludwig-Maximilians-Universität München Investigations into s-Heptazine-Based Carbon Nitride Precursors Andreas Sattler aus Augsburg 2010 Erklärung Diese Dissertation wurde im Sinne von § 13 Abs. 3 bzw. 4 der Promotionsordnung vom 29. Januar 1998 von Herrn Prof. Dr. Wolfgang Schnick betreut. Ehrenwörtliche Versicherung Diese Dissertation wurde selbstständig, ohne unerlaubte Hilfe erarbeitet. München, den 12.02.2010 Andreas Sattler Dissertation eingereicht am 15.02.2010 1. Gutachter: Prof. Dr. Wolfgang Schnick 2. Gutachter: Prof. Dr. Dirk Johrendt Mündliche Prüfung am 20. April 2010 ii Für meine Familie und Freunde Und für alle denen dies Information und Hilfe sein mag iii iv Acknowledgements First of all, I would like to express my gratitude to Prof. Dr. Wolfgang Schnick for hav- ing granted me the opportunity to work in his research group. His guidance and expertise have been invaluable for the present work. I am most grateful to Prof. Dr. Dirk Johrendt for his willingness to be the co-referee of this thesis. I thank Prof. Dr. Bettina V. Lotsch, Prof. Dr. Jürgen Senker, Prof. Dr. Konstantin Karaghiosoff and Priv. Doz. Dr. Klaus Müller-Buschbaum for being available as examiners in my viva-voce. The past and present members of the work group and other members of the department, whose company I have had the honor to enjoy, have helped and supported me in a multitude of ways. Working with these fine colleagues has become a part of my life that I will look back upon often and happily. I would like to address special thanks and gratitude to: My predecessors Dr. Barbara Jürgens and Prof. Dr. Bettina V. Lotsch and my succes- sors Sophia Makowski and Eva Wirnhier working on carbon nitride chemistry. I want to ex- press my gratitude for contributing in many discussions and for every-day help, ideas and inspirations they have offered. After the interlude represented by my works the research topic will be in female hands exclusively once more. All past and present members of laboratory D.2.103: Sophia Makowski and Eva Wirn- hier, Cordula Braun, Yamini Avadhut, Dr. Sabine Beyer, Stefanie Hering, Christian Minke, Stefan „Superflip“ Sedlmaier, Theresa Soltner, Dr. Johannes Weber are all thanked for con- tributing to this fine working environment. Christian Minke for conducting solid-state NMR and REM measurements; as well as for his willingness to compete in several word-play duels and for his helpful suggestions on improving the energy efficiency of our laboratory. Dr. Stefan Rannabauer, who very much inspired my interest in solid-state chemistry during my research practicum. I also want to express thanks to all my cooperation partners, especially: Prof. Dr. Jürgen Senker and his co-workers Daniel Gunzelmann, Dr. Jan Seyfarth and Dr. Lena Seyfarth for their expertise concerning solid-state NMR spectroscopy. As well as the PZZ team aka Dr. Sandro Pagano, Dr. Martin Zeuner and Alexander Zurawski who have worked with me on melamine melem adduct phases. My bachelor and research practicum students Lucia R. Lorenz, Michael R. Budde, Nicole Braml, Stefanie Schönberger, Simon Welzmiller whose drive and ambition have helped and supported this work a great deal. v Dr. Oliver Oeckler for his invaluable help concerning crystallographic problems. As well as for providing additional insights concerning several aspects of science and life in gen- eral like the many flaws of spectroscopy making it vastly inferior to diffraction, the needless- ness of noodles and the meaning of “rüftig” just to mention some select examples. Thomas Miller, Dr. Peter Mayer and Sandra Albrecht for measuring single-crystal data. Those who have been my fellow students all the way from undergraduate, especially: Daniel Bichler, Nina Hahn, Dr. Juliane A. Kechele, Phillipp Lorenz, Dr. S. Rebecca Römer, and Marc Thormählen. The other current members and alumni of solid-state chemistry (and associated groups) at LMU (in alphabetical order) Dr. Ulrich Baisch, Dr. Sascha Correll, Rainer Frankovsky, Cora Hecht, Elsbeth Hermanns, Frauke Hintze, Christoph Höller, Dr. Henning Höppe, Dr. Petra Jakubcova, Sebastian Junggeburth, Dr. Friedrich Karau, Dr. Alexandra Lieb, Catrin Löhnert, Saskia Lupart, Dr. Helen Müller, Dr. Abanti Nag, Dr. Regina Pocha, Florian „FloPu“ Pucher, Tobias Rosenthal, Marianne Rotter, Christoph „Rybi“ Rybak, Dr. Jörn Schmedt auf der Günne, Christian Schmolke, Matthias Schneider, Sebastian Schneider, Markus Seibald, Dr. Florian Stadler, Dr. Michael Tauchert, Marcus Tegel, Dr. Sabarinathan Venkatachalam, Wolfgang Wünschheim and Veronika Zinth. The other members of the department who have assisted me concerning analysis, ad- ministrative tasks and in many other ways. Dr. Markus Döblinger (TEM and ED), Dr. Bern- hard Kempf, Robert Eicher and Gertraud Käser (elemental analysis), Armin Andres (mass spectroscopy), Irmgard Peter (IR), Helmut „Piko“ Hartl (ICP–AES), Prof. Dr. Konstantin Karaghiosoff and Peter Mayer (solution-state NMR), and those working at the precision me- chanics and the glassblower workshops. Univ.- Prof. Dr. Hubert Huppertz and the past and present members of his group, which is now located at Innsbruck, whom I got to know during their time in Munich. Especially I would like to name, Dr. Johanna Knyrim, Dr. Gunter Heymann, Sonja Herlinka, Constantin Beyer and Dr. Holger Emme. And last, but not least, to all my friends, family and others who, though in a mostly non- chemical way, have helped me immeasurably. vi Science may set limits to knowledge, but should not set limits to imagination. Bertrand Russell (1872 - 1970) vii viii Contents Contents Contents..................................................................................................................................... 1 1. Introduction ...................................................................................................................... 4 1.1 Basic Concepts and Current State of Research ................................................................ 4 1.2 Carbon Nitride Compounds – a Historical Outline........................................................ 13 1.3 Goals of this Study ......................................................................................................... 18 2. Experimental Methods................................................................................................... 19 2.1 Preparative Methods....................................................................................................... 19 2.1.1 Vacuum and Inert Gas Line .................................................................................... 19 2.1.2 Furnaces .................................................................................................................. 19 2.1.3 Glove-Box ............................................................................................................... 19 2.1.4 Operation Techniques ............................................................................................. 20 2.2 Analytical Methods ........................................................................................................ 21 2.2.1 Diffraction Techniques............................................................................................ 21 2.2.2 Spectroscopic Methods ........................................................................................... 23 2.2.4 Thermal Analysis .................................................................................................... 24 2.2.5 Elemental Analysis.................................................................................................. 24 2.2.6 Mass Spectroscopy.................................................................................................. 25 2.2.7 Magnetic Measurements ......................................................................................... 25 3. The Formation of Melem............................................................................................... 26 3.1 Introduction .................................................................................................................... 26 3.2 Melamine Melem Adduct Phases................................................................................... 26 3.3 Oxygen-Containing Precursors – A Strategy Towards Oxo-Amino Heptazines? ......... 38 3.4 Enhancing the Synthesis of Melem................................................................................ 41 4. The Formation of Melam............................................................................................... 43 4.1 The Melamium Adduct C6N11H10Cl · 0.5NH4Cl............................................................ 43 4.2 The Melamium Melamine Adduct C6N11H10SCN · 2C3N3(NH2)3 ................................. 48 4.3 On the Potential of Thiourea as a Carbon Nitride Precursor.......................................... 52 5. Melemium Salts .............................................................................................................. 53 5.1 Introduction .................................................................................................................... 53 5.2 Melemium Melem Perchlorate....................................................................................... 53 5.3 Melemium Diperchlorate Sesquihydrate........................................................................ 58 5.3 Melemium Methylsulfonates.........................................................................................
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