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Und Cyaninfarbstoffen Diversitätsorientierte Multikomponentensynthese und Eigenschaften von Merocyanin- und Cyaninfarbstoffen Inaugural-Dissertation Zur Erlangung des Doktorgrades der Mathematisch-Naturwissenschaftlichen Fakultät der Heinrich-Heine-Universität Düsseldorf vorgelegt von Julian Papadopoulos aus Haan DÜSSELDORF, MÄRZ 2018 Aus dem Institut für Organische Chemie und Makromolekulare Chemie der Heinrich-Heine- Universität Düsseldorf Gedruckt mit der Genehmigung der Mathematisch-Naturwissenschaftlichen Fakultät der Heinrich-Heine-Universität Düsseldorf Referent: Prof. Dr. Thomas J.J. Müller Korreferent: PD Dr. Klaus Schaper Tag der mündlichen Prüfung: 25.05.2018 Meiner Familie gewidmet Die vorliegende Arbeit habe ich eigenständig und ohne unerlaubte Hilfe angefertigt. Die Dissertation wurde in der vorgelegten oder in ähnlicher Form noch bei keiner anderen Institution eingereicht. Ich habe bisher keine erfolglosen Promotionsversuche unternommen. Düsseldorf, den 29.05.2018 Julian Papadopoulos Die vorliegende Arbeit wurde in der Zeit von Januar 2014 bis März 2018 am Institut für Organische Chemie und Makromolekulare Chemie der Heinrich-Heine-Universität, Düsseldorf unter der Anleitung von Prof. Dr. Thomas J. J. Müller angefertigt. Danksagung Ich bedanke mich ganz herzlich bei Herrn Prof. Dr. Thomas J.J. Müller für die Möglichkeit meiner Promotion und der freundlichen Aufnahme an seinem Lehrstuhl, die interessante Aufgabenstellung und die hervorragende Betreuung meiner Arbeit. Bei Herrn PD Dr. Klaus Schaper bedanke ich mich für das Zweitgutachten dieser Arbeit und der hilfreichen Diskussionen. Allen Mitgliedern des Arbeitskreises danke ich für die freundliche Aufnahme und das entspannte Arbeitsklima während und außerhalb der Arbeitszeit, insbesondere Gereon Sommer und Tobias Deden für die Unterstützung während des gesamten Studiums. Meinem Laborkollegen Pascal Gesse möchte ich mich für die tolle Laboratmosphäre, die zahlreichen Gesänge und die phänomenalen Reden anlässlich meiner Geburtstage danken. Dr. Lucilla Levi danke ich für die kritische Durchsicht dieser Arbeit. Bei meinen Bachelorstudenten Laura Kloeters, Kay Merkens und Tabea Gerlach bedanke ich mich für ihr Engagement während ihren Bachelorarbeiten. Außerdem danke ich dem technischen und wissenschaftlichen Personal des Arbeitskreises Müller für die ständige Verfügbarkeit und die Gewährleistung eines reibungslosen Tagesablaufes. Maria Beuer danke ich für die Aufnahmen der zahlreichen NMR-Spektren und die Geduld bei den aufwendigen temperaturabhängigen NMR-Messungen. Für die Aufnahme der Massenspektren danke ich Herrn Bürgel und Herrn Dr. Tommes. Dr. Guido J. Reiß danke ich für die Aufnahme der Kristallstrukturdaten und die unkomplizierte Zusammenarbeit. Auch danke ich meinen Kooperationspartnern Anna Reiffers von der Arbeitsgruppe Gilch und Peter Pasch von der Arbeitsgruppe Hartmann für den reibungslosen Ablauf und die gute Kommunikation. Von Herzen bedanke ich mich bei meiner Familie und meiner Freundin Kathrin Bracht, ohne deren jahrelange Unterstützung meine Promotion nicht möglich gewesen wäre. Teile dieser Arbeit wurden bereits publiziert oder in Form von Postern auf Fachtagungen präsentiert. Publikationen in Fachzeitschriften • „Three-Component Synthesis and Photophysical Properties of Novel Coumarin-based Merocyanines”, J. Papadopoulos, K. Merkens, T. J. J. Müller, Chem. Eur. J. 2018, 24, 974-983. • „Highly fluorescent merocyanine and cyanine PMMA copolymers”, P. Pasch, J. Papadopoulos, A. Goralczyk, M. Tabatabai, T. J. J. Müller, L. Hartmann, Manuskript in Vorbereitung. • “Novel fluorescent 4-alkynylcoumarines”, J. Papadopoulos, T. J. J. Müller, Manuskript in Vorbereitung. Poster Präsentationen • „Novel One-Pot Syntheses of Merocyanine and Cyanine Dyes“ 27th European Colloquium on Heterocyclic Chemistry 2016, Amsterdam. • “Rapid One-Pot Synthesis of Coumarin-based Merocyanines” Conjugated Oligomers and Polymers 2015, Würzburg. • „Novel One-Pot Three-Component Synthesis of Merocyanines” ORCHEM 2014, Weimar. Betreute Bachelorarbeiten während der Promotion • „Entwicklung einer Dreikomponenten-Merocyanin-Synthese“, Laura Kloeters, 2014, Düsseldorf. • “Kupplungs-Additions-Synthese von Cumarin-Chromophoren”, Kay Merkens, 2015, Düsseldorf. • „Multikomponentensynthese von neuen Merocyaninen und Cyaninen“, Tabea Gerlach, 2016, Düsseldorf. Inhaltsverzeichnis 1 ZUSAMMENFASSUNG ........................................................................................1 2 ABSTRACT ..........................................................................................................5 3 EINLEITUNG UND AUFGABENSTELLUNG .......................................................8 4 ALLGEMEINER TEIL ......................................................................................... 13 4.1 Literaturübersicht und Kenntnisstand .................................................................................. 13 4.1.1 Polymethinfarbstoffe .......................................................................................................... 13 4.1.2 Sonogashira-Reaktion ....................................................................................................... 24 4.1.3 Michael-Addition ................................................................................................................ 26 4.2 Methoden .................................................................................................................................. 28 4.2.1 Absorptionsspektroskopie ................................................................................................. 28 4.2.2 Fluoreszenzspektroskopie ................................................................................................. 29 4.3 Darstellung der 4-Alkinylcoumarine 8 ................................................................................... 31 4.3.1 Literatur und Kenntnisstand ............................................................................................... 31 4.3.2 Synthese der Ausgangsverbindungen............................................................................... 37 4.3.3 Synthese von 4-Alkinylcoumarinen ................................................................................... 39 4.3.4 Strukturaufklärung ............................................................................................................. 44 4.3.5 Photophysikalische Eigenschaften .................................................................................... 49 4.3.6 Geometrieoptimierung und quantenchemische Betrachtungen ........................................ 59 4.3.7 Fazit ................................................................................................................................... 63 4.4 Dreikomponentensynthese von coumarinbasierten Merocyaninen 10 ............................. 64 4.4.1 Synthese der coumarinbasierten Merocyanine ................................................................. 64 4.4.2 Strukturaufklärung ............................................................................................................. 71 4.4.3 Photophysikalische Eigenschaften .................................................................................... 76 4.4.4 Geometrieoptimierung und quantenchemische Betrachtungen ........................................ 83 4.4.5 Fazit ................................................................................................................................... 86 4.5 Dreikomponenten- und Pseudo-Vierkomponentenreaktion von keton-basierten Merocyaninen 14 und Cyaninen 15 ................................................................................................... 89 4.5.1 Synthese der Ausgangsverbindung................................................................................... 90 4.5.2 Synthese der Merocyanine und Cyanine .......................................................................... 91 4.5.3 Strukturaufklärung ............................................................................................................. 96 4.5.4 Photophysikalische Eigenschaften .................................................................................... 99 4.5.5 DNA-Interkalation des Cyaninfarbstoffs .......................................................................... 103 4.5.6 Fazit ................................................................................................................................. 106 4.6 Dreikomponentenreaktion von Dicyanomerocyanine 20 .................................................. 108 4.6.1 Synthesekonzept und Literatur ........................................................................................ 108 4.6.2 Synthese der Ausgangsverbindungen............................................................................. 109 4.6.3 Synthese und Optimierung der Merocyanine .................................................................. 109 4.6.4 Strukturaufklärung ........................................................................................................... 116 4.6.5 Photophysikalische Eigenschaften .................................................................................. 122 4.6.6 Fazit ................................................................................................................................. 125 5 ANHANG .......................................................................................................... 126 5.1 Synthese des terminalen Alkins 7f .....................................................................................
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