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Diarylacetyene-linked [60]fullerene dumbbells via metal-catalyzed couplings
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.ORCID iD: 0000-0003-3701-4935
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.ORCID iD: 0000-0003-3223-5456
(English)Manuscript (preprint) (Other academic)
Abstract [en]

This preliminary manuscript describes the synthesis and characterization of new di(4-bromoaryl)acetylenes by Sonogashira cross-coupling, initial attempts to transform model aryl bromides to aryl boronic acids as well as a model study of Rh-catalysed hydroarylation of [60]fullerene with aryl boronic acids, aiming towards “all carbon”-linked [60]fullerene dumbbells.

Keywords [en]
Fullerene, Metal-catalyzed addition, Sonogashira, Hydroarylation
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-327164OAI: oai:DiVA.org:uu-327164DiVA, id: diva2:1129651
Available from: 2017-08-04 Created: 2017-08-04 Last updated: 2017-08-06
In thesis
1. Carbon Nanostructures – from Molecules to Functionalised Materials: Fullerene-Ferrocene Oligomers, Graphene Modification and Deposition
Open this publication in new window or tab >>Carbon Nanostructures – from Molecules to Functionalised Materials: Fullerene-Ferrocene Oligomers, Graphene Modification and Deposition
2017 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

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.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2017. p. 64
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1537
Keywords
Fullerenes, Graphene, Deposition, Functionalization, Organometallic complexes
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-327189 (URN)978-91-513-0019-1 (ISBN)
Public defence
2017-09-22, A1:107a, BMC, Husargatan 3, Uppsala, 09:15 (English)
Opponent
Supervisors
Available from: 2017-08-28 Created: 2017-08-06 Last updated: 2017-09-08

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