Synthesis of Substituted Bacteriochlorins
| dc.contributor.advisor | Christian Melander, Committee Member | en_US |
| dc.contributor.advisor | Jonathan Lindsey, Committee Chair | en_US |
| dc.contributor.advisor | Bruce Novak, Committee Member | en_US |
| dc.contributor.author | Meneely, Kelly Rose | en_US |
| dc.date.accessioned | 2010-08-19T18:20:04Z | |
| dc.date.available | 2010-08-19T18:20:04Z | |
| dc.date.issued | 2010-04-22 | en_US |
| dc.degree.discipline | Chemistry | en_US |
| dc.degree.level | thesis | en_US |
| dc.degree.name | MS | en_US |
| dc.description.abstract | The objective of this work is two-fold: first, to find new conditions to improve the condensation reactions leading to the macrocycles 3,13-dibromo-5-methoxybacteriochlorin (BC-Br3OMe5Br13) and 3,13-dibromobacteriochlorin (BC-Br3Br13), and second, to functionalize the valuable BC-Br3OMe5Br13 building block. This work improves upon past condensation methods, which afforded low yields of bacteriochlorin with an inseparable chlorin product during formation of BC-Br3Br13, and provided no access to BC-Br3OMe5Br13. Through microscale optimization of conditions, solvents, concentrations, Lewis acids, and additives, BC-Br3OMe5Br13 and BC-Br3Br13 were isolated in 42% and 30% yield, respectively. Several derivatizations including diacetylation of BC-Br3OMe5Br13 was achieved in 70% yield, followed by bromination at the β-position in 22% yield. Stille coupling of BC-Br3OMe5Br13 to introduce a formyl group was performed in 30% yield. Two TIPS-ethynyl groups were also installed on BC-Br3OMe5Br13 in 4.7% yield. | en_US |
| dc.identifier.other | etd-03232009-191106 | en_US |
| dc.identifier.uri | http://www.lib.ncsu.edu/resolver/1840.16/6351 | |
| dc.rights | I hereby certify that, if appropriate, I have obtained and attached hereto a written permission statement from the owner(s) of each third party copyrighted matter to be included in my thesis, dis sertation, or project report, allowing distribution as specified below. I certify that the version I submitted is the same as that approved by my advisory committee. I hereby grant to NC State University or its agents the non-exclusive license to archive and make accessible, under the conditions specified below, my thesis, dissertation, or project report in whole or in part in all forms of media, now or hereafter known. I retain all other ownership rights to the copyright of the thesis, dissertation or project report. I also retain the right to use in future works (such as articles or books) all or part of this thesis, dissertation, or project report. | en_US |
| dc.subject | porphyrin | en_US |
| dc.subject | bacteriochlorin | en_US |
| dc.subject | chlorin | en_US |
| dc.title | Synthesis of Substituted Bacteriochlorins | en_US |
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