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STUDIES OF YAMAMOTO AND SUZUKI POLYMERIZATIONS OF DIBROMOFLUORENES. SYNTHESIS AND SPECTROSCOPY OF FLUORENE MACROCYCLES AND COPOLYMERS
by
Nadezda Fomina
A Dissertation Presented to the
FACULTY OF THE GRADUATE SCHOOL
UNIVERSITY OF SOUTHERN CALIFORNIA
In Partial Fulfillment of the
Requirements for the Degree
DOCTOR OF PHILOSOPHY
(CHEMISTRY)
August 2009
Copyright 2009 Nadezda Fomina
Object Description
| Title | Studies of yamamoto and suzuki polymerizations of dibromofluorenes: synthesis and spectroscopy of fluorene macrocycles and copolymers |
| Author | Fomina, Nadezda |
| Author email | fomina@usc.edu; chombikster@gmail.com |
| Degree | Doctor of Philosophy |
| Document type | Dissertation |
| Degree program | Chemistry |
| School | College of Letters, Arts and Sciences |
| Date defended/completed | 2009-03-12 |
| Date submitted | 2009 |
| Restricted until | Unrestricted |
| Date published | 2009-08-07 |
| Advisor (committee chair) | Hogen-Esch, Thieo E. |
| Advisor (committee member) |
Petasis, Nicos Bradforth, Stephen Prakash, Surya Nutt, Steven |
| Abstract | This dissertation describes the synthesis of macrocyclic polyfluorenes and fluorene copolymers, end-functionalization of polyfluorenes, conformational studies of polyfluorene chains in dilute solution and kinetics of Yamamoto polymerization.; Chapter 1 summarizes a history of semiconducting polymers, the importance of polyfluorenes as blue light-emitting materials and the progress that has been made in the area of polyfluorene-based organic light-emitting diodes.; Chapter 2 describes the synthesis of a new fluorene monomer, 3,6-dibromo-9,9-dihexylfluorene. This monomer is successfully polymerized by Yamamoto coupling reaction to yield macrocyclic polyfluorenes with the number of fluorene units from 4 to 13. The cyclic tetramer is isolated as the major cyclic product and its spectral properties are investigated.; Chapter 3 includes the synthesis of new polyfluorene copolymers containing different mole fractions of 3,6-fluorene units. The introduction of the 3,6-linkages is shown to give rise to a blue shift in absorption and emission spectra of polyfluorenes. The nature of the blue shift is studied via the model mixed 2,7-co-3,6-fluorene oligomers.; Chapter 4 demonstrates end-functionalization of polyfluorenes by Yamamoto reaction. A number of new end-capping reagents is investigated. It is found that the introduction of ortho-substituents into end-capping molecules yields a higher degree of end-capping and higher molecular weight products.; Chapter 5 presents the conformational studies of polyfluorenes in dilute solution. Density functional theory (DFT) calculations are employed to model the conformations of the polyfluorene oligomers and this data is used to simulate the behavior of high molecular weight polyfluorenes.; Chapter 6 deals with the kinetic studies of polymerization of 2,7-dibromo-9,9-dihexylfluorene by Yamamoto reaction. DFT calculations of the reactive intermediates were performed and suggest that the rate of polymerization is chain length dependent. |
| Keyword | polyfluorenes; 3,6-dibromofluorene; fluorene macrocycle; Yamamoto coupling |
| Language | English |
| Part of collection | University of Southern California dissertations and theses |
| Publisher (of the original version) | University of Southern California |
| Place of publication (of the original version) | Los Angeles, California |
| Publisher (of the digital version) | University of Southern California. Libraries |
| Provenance | Electronically uploaded by the author |
| Type | texts |
| Legacy record ID | usctheses-m2538 |
| Rights | Fomina, Nadezda |
| Repository name | Libraries, University of Southern California |
| Repository address | Los Angeles, California |
| Repository email | http://www.usc.edu/isd/libraries/services/ask_a_librarian/email/ |
| Filename | etd-Fomina-2766 |
| Archival file | uscthesesreloadpub_Volume23/etd-Fomina-2766.pdf |
Description
| Title | Page 1 |
| Full text | STUDIES OF YAMAMOTO AND SUZUKI POLYMERIZATIONS OF DIBROMOFLUORENES. SYNTHESIS AND SPECTROSCOPY OF FLUORENE MACROCYCLES AND COPOLYMERS by Nadezda Fomina A Dissertation Presented to the FACULTY OF THE GRADUATE SCHOOL UNIVERSITY OF SOUTHERN CALIFORNIA In Partial Fulfillment of the Requirements for the Degree DOCTOR OF PHILOSOPHY (CHEMISTRY) August 2009 Copyright 2009 Nadezda Fomina |
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