Please use this identifier to cite or link to this item:
https://knowledgecommons.lakeheadu.ca/handle/2453/4342
Title: | Organic semiconductors containing multi-heteroatom rings |
Authors: | Agyei, Clifford |
Keywords: | Semiconductivity;Hetero(aromatic) compounds;Sandmeyer reactions with heterocycles |
Issue Date: | 2018 |
Abstract: | Oligomers of thiophene are ubiquitous in molecular materials research. Other ring systems, especially those lacking at least C2v symmetry are much less common. We investigated thiophene-thiazole, pyrrole-thiazole, thiophene-furan, and thiophene-selenophene co-oligomers, which nominally have the same conjugation length and physical dimensions as thiophene oligomers but contain a heteroatom, that should impact the electronic properties. The lower symmetry of the 1,3-thiazole system, among other attributes, makes these new systems chemically challenging to synthesize; however, the electronic and steric variability makes them interesting targets. One common method of synthesizing thiazole is the ring-closing reaction that generates an amino-substituted thiazole. We have done a systematic study to convert the aminothiazole to a more useful synthon using Sandmeyer conditions. We herein present the synthesis, characterization, and molecular or photoelectronic structures of selected mixed oligomer systems, along with a computational study to measure bond length alternation, localization indices, and HOMO-LUMO (band gap) energy. Aminothiazole can be deaminated using Sandmeyer conditions. As conjugation length increases with the addition of a more electron withdrawing group, there is a general decrease of the band gap as well as of the HOMO- LUMO energies. |
URI: | http://knowledgecommons.lakeheadu.ca/handle/2453/4342 |
metadata.etd.degree.discipline: | Chemistry |
metadata.etd.degree.name: | Master of Science |
metadata.etd.degree.level: | Master |
metadata.dc.contributor.advisor: | Mackinnon, Craig |
metadata.dc.contributor.committeemember: | Mawhinney, Robert Kinrade, Stephen Ylijoki, Kai |
Appears in Collections: | Electronic Theses and Dissertations from 2009 |
Files in This Item:
File | Description | Size | Format | |
---|---|---|---|---|
AgyeiC2018m-1b.pdf | 2.96 MB | Adobe PDF | ![]() View/Open |
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.