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Synthesis and IR Spectroelectrochemical Studies of a [60]Fulleropyrrolidine-(tricarbonyl)chromium Complex: Probing C-60 Redox States by IR Spectroscopy
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Photochemistry and Molecular Science.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Photochemistry and Molecular Science, Molecular Biomimetics.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
2011 (English)In: European Journal of Inorganic Chemistry, ISSN 1434-1948, E-ISSN 1099-1948, no 11, 1744-1749 p.Article in journal (Refereed) Published
Abstract [en]

The synthesis of a new fulleropyrrolidine-(tricarbonyl)chromium complex: 1-methyl-2-(4-methoxyphenyl)-3,4-[60]fulleropyrrolidine-(tricarbonyl)chromium is described together with its characterization by IR, NMR and cyclic voltammetry. IR spectro-electrochemistry has been used to probe the redox level of the fullerene derivative via the relative position of the vibrational bands of the CO ligands, which are sensitive to the electronic state of the complex. Other strategies to incorporate a tricarbonylchromium moiety to fullerene C60 are also briefly discussed and evaluated.

Place, publisher, year, edition, pages
John Wiley & Sons, 2011. no 11, 1744-1749 p.
Keyword [en]
Fullerenes, Chromium, IR spectroscopy, Cyclic voltammetry, Redox chemistry, Electrochemistry
National Category
Chemical Sciences
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-148456DOI: 10.1002/ejic.201100011ISI: 000289354900008OAI: oai:DiVA.org:uu-148456DiVA: diva2:402187
Available from: 2011-03-07 Created: 2011-03-07 Last updated: 2017-12-11
In thesis
1. Chemistry of Carbon Nanostructures: Functionalization of Carbon Nanotubes and Synthesis of Organometallic Fullerene Derivatives
Open this publication in new window or tab >>Chemistry of Carbon Nanostructures: Functionalization of Carbon Nanotubes and Synthesis of Organometallic Fullerene Derivatives
2011 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis is based on two main parts. The first part concerns purification and functionalization of carbon nanotubes (papers I-III), and the second part is related to the synthesis of organometallic fullerene derivatives (papers IV-VII):

Two oxidative methods involving aqueous nitric acid were compared with respect to their capability to introduce carboxylic groups into single walled carbon nanotubes, and several literature methods for esterification and amidation of these groups have been evaluated with focus on efficiency and reproducibility in forming covalently functionalized products soluble in organic media. Amidation proceeding via a SWNT-(COCl)n intermediate yielded the expected covalent product, whereas carboxylate salt formation dominated with other attempted methods. Esterification was achieved via the acyl chloride method and via alkylation of SWNT-(COO)n, the latter being the more efficient method.

A new, reagent-free method for purification of single- and multi walled carbon nanotubes has been developed. Microwave treatment dissociates non-nanotube carbon and disperses it into an organic solvent, resulting in very pure carbon nanotubes within a few minutes of heating, without the involvement of acidic/oxidative reagents. According to thermogravimetric analysis, Raman and IR spectroscopy, as well as SEM, the process yields nanotubes with a low degree of defects.

A non-covalent approach has been employed to prepare nanotubes functionalized with glycosides. Derivatives of galactose and lactose were covalently linked to a pyrene moiety and the thus formed pyrene-glycosides were non-covalently attached to single- and multi walled carbon nanotubes by π-π interactions. Fluorescence titrations have been used to quantify the formed supramolecular assemblies, which for SWNTs exhibits increased water solubility.

A fulleropyrrolidine-(tricarbonyl)chromium complex was synthesized and fully characterized. IR spectroelectrochemistry was used to probe the redox state of the fullerene and provided evidence for electronic communication between the two electroacive moieties. A C60-ferrocene-C60 triad system was synthesized and characterized. Cyclic voltammetry and fluorescence studies suggested electronic communication between ferrocene and the two fullerenes. Finally, the synthesis and initial characterization of short fullerene-ferrocene oligomers are presented.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2011. 62 p.
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 859
Keyword
Carbon nanotubes, Fullerenes, Purification, Functionalization, Organometallic complexes
National Category
Organic Chemistry
Research subject
Chemistry with specialization in Organic Chemistry
Identifiers
urn:nbn:se:uu:diva-159315 (URN)978-91-554-8170-4 (ISBN)
Public defence
2011-11-10, B7:101a, BMC, Husargatan 3, Uppsala, 09:30 (English)
Opponent
Supervisors
Available from: 2011-10-19 Created: 2011-09-27 Last updated: 2011-11-04Bibliographically approved

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Andersson, Claes-HenrikBerggren, GustavOtt, SaschaGrennberg, Helena

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