Studies towards two-dimensional polymers based on cyclic monomers with photoreactive 1,8-diazaanthracenes
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1 Research Collection Doctoral Thesis Studies towards two-dimensional polymers based on cyclic monomers with photoreactive 1,8-diazaanthracenes Author(s): Li, Ming Publication Date: 2013 Permanent Link: Rights / License: In Copyright - Non-Commercial Use Permitted This page was generated automatically upon download from the ETH Zurich Research Collection. For more information please consult the Terms of use. ETH Library
2 DISS. ETH NO Studies towards two-dimensional polymers based on cyclic monomers with photoreactive 1,8-diazaanthracenes A dissertation submitted to ETH ZURICH for the degree of Doctor of Sciences presented by Ming Li Master of Science, Tsinghua University November 14, 1984 citizen of China accepted on the recommendation of Prof. Dr. A. Dieter Schlüter, examiner Prof. Dr. Paul Smith, coexaminer Dr. Bernd Schweizer, coexaminer Prof. Dr. Peter Johann Walde, coexaminer Dr. Anzar Khan, coexaminer 2013
3 Zusammenfassung Zusammenfassung Ein zwei-dimensionales (2D) Polymer ist ein kovalent gebundenes, eine Monomereinheit dickes, lateral unendliches molekulares Nanosheet, welches eine periodische Fernordnung der internen Struktur aufweist. Die neuesten Erkenntnisse betreffend Graphen (ein Kohlstoff-2D Polymer) und eine begrenzte Anzahl anderer anorganischer Nanosheets haben mögliche Anwendungsbereich von 2D Polymeren eröffnet. In dieser Doktorarbeit wurden fünf genau definierte Form erhaltende Diazaarylen (DAA) ethynylene Makrozyklen synthetisiert. Ausserdem wurde ihr Potential als Ausgangsverbindungen für 1D/2D Polymere untersucht. Schlüsselpunkt dieser Polymerisationen ist eine photochemisch induzierte [4+4]-Zykloaddition zwischen parallel zueinander angeordneten, aber gegensätzlich orientierten DAA Einheiten. Dies betrifft im Speziellen die Photo-Polymerisation in Einkristallen um stabförmige 1D Polymere herzustellen, aber auch erste orientierende Studien für die Synthese von 2D Polymeren in Lösung oder in flüssig kristalliner Phase. Der erste Teil beschreibt das Design und die Synthese der Modelverbindung (M), welche eine DAA Einheit besitzt. Des Weiteren wird die Synthese von fünf unterschiedlichen Makrozyklen für die Photo- Polymerisation durch laterales Wachstum behandelt. Modelverbindung M wurde verwendet, um die DAA Photoreaktivität zu untersuchen, wobei der Fokus hier auf dem Aspekt der relativen Orientierung und dem Reaktionsumsatz lag. V
4 Zusammenfassung Der zweite Teil befasst sich mit der Polymerisation von ausgewählten Verbindungen in Einkristallen. M2a wurde durch Photobestrahlung zu einem stabförmigen 1D Polymer umgesetzt. Es ist damit zum ersten Mal gelungen, dieanthrazeneinheiten einer so komplexen Verbindung im Einkristall zu dimerisieren. Das Polymer wurde mittels NMR Spektroskopie sowie GPC und AFM im tapping Modus nach Ablagerung auf HOPG untersucht. Bedauerlicherweise konnte dieselbe Vorgehensweise nicht für M3a, M3b, M3c oder M3d angewandt werden, da in den Kristallen dieser Verbindungen die Antrazeneinheiten nicht die zur Dimerisierung notwendige parallele Anordnung aufweisen. Hingegen liegt in diesen Fällen eine interne Stapelungsstruktur vor, welche sich nicht für eine laterale Polymerisation zu einem 2D Polymer eignet. Verschiedenste Ansätze die interne Ordnung zu verändern scheiterten. Im dritten Teil der Arbeit werden weitere orientierende Ergebnisse beschrieben. Diese Analysen wurden mit Hinblick darauf durchgeführt, herauszufinden, ob Verbindung M3d für Polymerisationen in Lösung oder in flüssig kristalliner Phase herangezogen werden kann. Obwohl die Resultate noch nicht aussagekräftig genug sind, um Rückschlüsse zu ziehen, geben sie eine Rechtfertigung auf diesem Gebiet weiterhin intensive Forschung zu betreiben, was im Rahmen dieser Doktorarbeit nicht mehr möglich war. VI
5 Abstract Abstract A 2D polymer is a covalently bonded, one monomer unit thick, laterally infinite molecular nanosheet possessing a periodic long range order of internal structure. The recent development of graphene (carbon 2D polymer) and a limited number of other inorganic nanosheets has opened new gate ways for the possibilities and applications for 2D polymers. Within this thesis, five well-defined shape persistent diazaarylene (DAA) ethynylene macrocycles were synthesized and their potential as monomers for the polymerization towards 1D/2D polymers is investigated. Key of these polymerizations is the photochemically induced [4 + 4]- cycloaddition between the face-to-face stacked but oppositely oriented DAA units of these potential monomers. This particularly concerns photopolymerization in single crystals towards a novel 1D rod-shape polymer but also first orienting studies towards synthesizing 2D polymers in solution or liquid crystalline phases. The first part describes the design and the synthesis of a model compound (M) which carries a DAA unit and also of five macrocycles for photo-polymerization through lateral growth. Model M is used to investigate the DAA photoreactivity focussing on the aspect of relative orientation and reaction conversion. The second part of the thesis is dealing with the polymerization of selected compounds in single crystals. Compound M2a which embed two photoreactive DAA units is converted into a 1D rod-shape polymer upon VII
6 Abstract photo-irradiation which represents the first case ever in which anthracene dimerization of such a complex compound could be realized in a single crystal. The polymer is analysed by NMR spectroscopy, GPC and tapping mode AFM imaging after deposition on HOPG. Unfortunately, the same protocol could not be successfully applied to compound M3a, M3b, M3c, and M3d which embed three DAA units because these compounds do not crystallize in an internal packing that would allow for lateral polymerizations into 2D polymers to take place. Various attempts of changing the internal order did unfortunately not lead to a breakthrough. In a third part very exploratory results are briefly described, all of which aim at finding out whether compound M3d which is decorated with alkyl tails can be used for polymerization in solution and liquid crystalline phases. While the results are far too premature to allow any conclusions to be drawn, they provide a justification to proceed into this direction with much more effort, which, for time reasons, could not be invested anymore within the present thesis. VIII
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