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Carbon Nanostructures – from Molecules to Functionalised Materials Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology 1537 Carbon Nanostructures – from Molecules to Functionalised Materials Fullerene-Ferrocene Oligomers, Graphene Modification and Deposition MICHAEL NORDLUND ACTA UNIVERSITATIS UPSALIENSIS ISSN 1651-6214 ISBN 978-91-513-0019-1 UPPSALA urn:nbn:se:uu:diva-327189 2017 Dissertation presented at Uppsala University to be publicly examined in A1:107a, BMC, Husargatan 3, Uppsala, Friday, 22 September 2017 at 09:15 for the degree of Doctor of Philosophy. The examination will be conducted in English. Faculty examiner: Professor Mogens Brøndsted Nielsen (Copenhagen University, Department of chemistry). Abstract Nordlund, M. 2017. Carbon Nanostructures – from Molecules to Functionalised Materials. Fullerene-Ferrocene Oligomers, Graphene Modification and Deposition. Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology 1537. 64 pp. Uppsala: Acta Universitatis Upsaliensis. ISBN 978-91-513-0019-1. The work described in this thesis concerns development, synthesis and characterisation of new molecular compounds and materials based on the carbon allotropes fullerene (C60) and graphene. A stepwise strategy to a symmetric ferrocene-linked dumbbell of fulleropyrrolidines was developed. The versatility of this approach was demonstrated in the synthesis of a non- symmetric fulleropyrrolidine-ferrocene-tryptophan triad. A new tethered bis-aldehyde, capable of regiospecific bis-pyrrolidination of a C60-fullerene in predominantly trans fashion, was designed, synthesised and reacted with glycine and C60 to yield the desired N-unfunctionalised bis(pyrrolidine)fullerene. A catenane dimer composed of two bis(pyrrolidine)fullerenes was obtained as a minor co-product. From the synthesis of the N-methyl analogue, the catenane dimer could be separated from the monomeric main product and fully characterised by NMR spectroscopy. Working towards organometallic fullerene-based molecular wires, the N-unfunctionalised bis(pyrrolidine)fullerene was coupled to an activated carboxyferrocene- fullerene fragment by amide links to yield a ferrocene-linked fullerene trimer, as indicated by mass spectrometry from reactions carried out at small scale A small library of conjugated diarylacetylene linkers, to be coupled to C60 via metal-mediated hydroarylation, was developed. Selected linker precursors were prepared and characterised, and the hydroarylation has been adapted using simple arylboronic acids. Few-layer graphene was prepared and dip-deposited from suspension onto a piezoelectric polymer substrate. Spontaneous side-selective deposition was observed and, from the perspective of non-covalent interaction, rationalised as being driven by the inbuilt polarization of the polymer. Aiming for selectively edge-oxidized graphene, a number of graphitic materials were treated with a combination of ozone and hydrogen peroxide under sonication. This mild, metal-free procedure led to edge-oxidation and exfoliation with very simple isolation of clean materials indicated by microscopy, spectroscopy, and thermogravimetric analysis. Keywords: Fullerenes, Graphene, Deposition, Functionalization, Organometallic complexes Michael Nordlund, Department of Chemistry - BMC, Organic Chemistry, Box 576, Uppsala University, SE-75123 Uppsala, Sweden. © Michael Nordlund 2017 ISSN 1651-6214 ISBN 978-91-513-0019-1 urn:nbn:se:uu:diva-327189 (http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-327189) In this house, we obey the laws of thermodynamics! – The Simpsons To my family. List of Papers This thesis is based on the following papers, which are referred to in the text by their Roman numerals: I Nordlund, M., Andersson, C.-H., Grennberg, H. Mono- and diamides of 1,1’-dicarboxyferrocene: a stepwise approach to ferrocene-interlinked fullerene oligomers. Manuscript II Nordlund, M., Günther, T., Andersson, C.-H., Grennberg, H. Catenane dimer formation in tether-assisted trans-bis- pyrrolidination of [60]fullerene. Manuscript III Nordlund, M., Andersson, C.-H., Grennberg, H. Towards fullerene-based molecular wires: amide-interlinked ferro- cene-fullerene oligomers. Manuscript IV Nordlund, M., Kazen Orrefur, J., Grennberg, H. Diarylacety- lene-linked fullerene dumbbells via metal-catalysed cou- plings. Preliminary manuscript V Nordlund, M., Bhandary, S., Sanyal, B., Löfqvist, T., Grenn- berg, H. Side-selective self-assembly of graphene and FLG on piezoelectric PVDF from suspension. Journal of Physics D: Applied Physics, 2016, 49(7):07LT01 VI Lundstedt, A., Nordlund, M., Ahlberg, P., Grennberg, H. Edge oxidation of graphite using a combined hydrogen peroxide - ozone treatment under sonication conditions. Manuscript Reprints were made with permission from the respective publishers. Contribution Report The author wishes to clarify his contribution to the research presented in papers I-VI in the thesis. I Contributed to formulating a research problem. Conducted and optimised parts of the synthesis and characterisation. Wrote the first draft and contributed to the writing of the final manu- script. II Contributed to formulating a research problem. Designed the synthesis of the improved tether. Planned and performed a significant part of the experimental work. Supervised part of the synthesis. Contributed to the writing of the manuscript. III Contributed to the design of the target compound. Performed parts of the experimental work and characterisation. Signifi- cantly contributed to the writing of the manuscript. IV Formulated the research problem and planned the project. Per- formed a significant part of the experimental work. Supervised part of the synthesis. Wrote the first draft and contributed to the writing of the final manuscript. V Performed all of the experiments, Raman, IR, UV/vis and LOM characterisation, and contact angle measurements. Sig- nificantly contributed to the writing of the manuscript. VI Contributed to formulating a research problem and planning. Co-performed all of the experiments. Performed all LOM, UV/vis, and Raman characterisation. Significantly contributed to the writing of the manuscript. The author also wishes to point out that parts of this thesis are based on a previous thesis, which was submitted for his licentiate degree in 2015. Up- dated content has been largely rewritten, expanded with current results, and adapted to the format of a doctoral thesis. Nordlund, M., Carbon Nanostructures and Nanotechnology: Graphene on Polymer Substrates and Organometallic Fullerene Oligomers. Fil. Lic. thesis, Acta Universitatis Upsaliensis, 2015 Contents 1 Introduction ......................................................................................... 11 1.1 Carbon allotropes ............................................................................ 12 1.2 Fullerene background ...................................................................... 14 1.3 Functionalisation of C60-fullerenes ................................................. 15 1.4 Graphite and graphene .................................................................... 18 1.4.1 Production of graphene .......................................................... 19 1.4.2 Deposition of graphene from suspension ............................... 22 1.5 Characterisation methods ................................................................ 23 1.5.1 Molecules ............................................................................... 23 1.5.2 Materials ................................................................................ 24 2 Molecules to materials – a fullerene story (Papers I-IV) ..................... 26 2.1 Introduction ..................................................................................... 26 2.2 Stepwise approach to C60-dumbbells .............................................. 28 2.3 Towards longer oligomers .............................................................. 30 2.4 Novel fullerene-based dumbbells .................................................... 38 2.4.1 Metal-catalysed hydroarylation of fullerenes ........................ 39 2.4.2 Fullerene dumbbells via metal-catalysed hydroarylation ...... 40 2.5 Conclusion ...................................................................................... 42 3 Graphene story (Papers V-VI) ............................................................. 44 3.1 Introduction ..................................................................................... 44 3.2 Manufacture and deposition of FLG ............................................... 44 3.3 Mild oxidation of graphitic materials .............................................. 48 3.4 Conclusion ...................................................................................... 51 4 Concluding remarks and outlook ......................................................... 52 5 Acknowledgments ............................................................................... 53 6 Populärvetenskaplig sammanfattning på svenska ................................ 55 7 References ........................................................................................... 57 Abbreviations AIBN Azobisisobutyronitrile γ-CD γ-Cyclodextrin CNT Carbon nanotube cod 1,5-Cyclooctadiene COSY Correlation spectroscopy CV Cyclic voltammetry CVD Chemical vapor deposition DCE 1,2-Dichloroethane DCM Dichloromethane DEA Diethylamine DFT Density functional theory DMF Dimethylformamide DOSY Diffusion-ordered spectroscopy FLG Few-layer graphene GO Graphene oxide GPC
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