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Chloro-, aryl-, and perfluoroalkylfullerenes

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dc.contributor.authorKuvychko, Igor V., author
dc.contributor.authorStrauss, Steven H., advisor
dc.contributor.authorPrieto, Amy L. (Amy Lucia), committee member
dc.contributor.authorHochheimer, Hans D., committee member
dc.contributor.authorRappé, Anthony K., 1952-, committee member
dc.contributor.authorElliott, Cecil Michael, committee member
dc.date.accessioned2007-01-03T04:31:08Z
dc.date.available2007-01-03T04:31:08Z
dc.date.issued2009
dc.descriptionDepartment Head: Anthony K. Rappé.
dc.description.abstractThe preparation, properties, stability, and handling of three classes of fullerene derivatives, chloro-, aryl-, and perfluoroalkylfullerenes, were studied in detail, in some cases for the first time. The same general methodology was used throughout this work: i) analytical methodology was developed and optimized using internal standards of known composition and purity; ii) the preparation of new compounds was studied by mapping the space of different reaction conditions using the newly developed analytical methods; iii) the efficient synthetic methods for the preparation of individual pure compounds were developed based on the mapping; iv) the pure compounds were characterized and their stability, or lack thereof, was studied. The first detailed study of fullerene chlorination led to isolation and characterization of several new chlorofullerenes: o-C60Cl2; p-C60Cl2; C60Cl4; C60Cl10; C70Cl6; and C70Cl8. It was discovered that chlorofullerenes are generally photosensitive in solution, both in the presence and absence of air and moisture. Effective methods for handling chlorofullerenes were developed (including a specialized crystallization technique). The experimental findings and theoretical calculations revealed the fundamental patterns governing multiple additions to fullerene cages. The efficient preparation of aryl- and perfluoroalkylfullerenes from chlorofullerene synthons was developed, leading to high yields of aryl- and mixed perfluoroethyl/hydrofullerenes (i.e., C60(C2F5)5H and C60(C2F5)3H). The first example of an organometallic complex of a perfluoroalkylfullerene was prepared using C60(C2F5)5H as a synthon. The direct addition of thermally-generated CF3 radicals to fullerenes was also studied. A specialized reactor was designed and built in order to validate mechanistic hypotheses. Good agreement between the experimental observations and predictions based on the hypotheses was observed. It led to the development of a new approach to efficient synthesis of C60(CF3)n with low values of n, including an unprecedented selective synthesis of C60(CF3)2 from unpurified fullerene extract.
dc.format.mediumdoctoral dissertations
dc.identifier2009_summer_Kuvychko_CHEM.pdf
dc.identifierETDF2009100002CHEM
dc.identifier.urihttp://hdl.handle.net/10217/37478
dc.languageEnglish
dc.language.isoeng
dc.publisherColorado State University. Libraries
dc.relationCatalog record number (MMS ID): 991014743119703361
dc.relationQD181.C1.K89 2009
dc.relation.ispartof2000-2019
dc.rightsCopyright and other restrictions may apply. User is responsible for compliance with all applicable laws. For information about copyright law, please see https://libguides.colostate.edu/copyright.
dc.titleChloro-, aryl-, and perfluoroalkylfullerenes
dc.typeText
dcterms.rights.dplaThis Item is protected by copyright and/or related rights (https://rightsstatements.org/vocab/InC/1.0/). You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).
thesis.degree.disciplineChemistry
thesis.degree.grantorColorado State University
thesis.degree.levelDoctoral
thesis.degree.nameDoctor of Philosophy (Ph.D.)

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