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SYNTHESIS OF ALKYLSILANES FOR USE AS MOLECULAR DIODES AND SYNTHESIS OF CHEMICALLY MODIFIED ALGINATE FOR ENVIRONMENTALLY SENSITIVE ORAL DRUG DELIVERY

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title
SYNTHESIS OF ALKYLSILANES FOR USE AS MOLECULAR DIODES AND SYNTHESIS OF CHEMICALLY MODIFIED ALGINATE FOR ENVIRONMENTALLY SENSITIVE ORAL DRUG DELIVERY
author
Morningstar, John Tanner
abstract
Abstract Molecular electronics is a continuously growing field which attempts to solve the problem that their solid-state counterparts encounter with continuing to grow smaller while maintaining the same functionality. Although successful molecular electronics have been created, their level of functionality does not yet match solid states. Furthering the field involves elucidating the mechanism of rectification and continuing to grow the library of compounds available. To accomplish this, we have successfully synthesized twenty new alkylsilanes which exhibit rectification behavior. We were able to draw several conclusions about promising scaffolds through examination of terminal groups with electron withdrawing and donating substituents, nitrogen heterocycles, and sterically hindered substituents. Additionally, our compounds were subjected to doping of the self-assembled monolayer devices which we found to benefit rectification. It was hypothesized that adding electron withdrawing groups, large and soft atoms, and groups with non-bonding electrons would also boost rectification. We obtained compounds with R ratios as high as 8500. This value is the highest our group has achieved to date. Biopolymers are commonly used as drug delivery scaffolds due to their safety and resistance to environmental stimuli. Alginate is one such polymer which has garnered increased attention as of late. To improve the properties of alginate for this purpose, we have developed a method to quantitatively modify the backbone of alginate with small molecules via sodium periodate oxidation and reductive amination of the corresponding oxidized product. Examining the difference in modified alginate with a small unsubstituted aromatic ring as well as an aromatic ketone, ester, and carboxylic acid allowed us to determine which molecules are beneficial to environmental pH sensitivity. We successfully synthesized three new quantitatively modified alginates and examined their pH sensitivity using hydrogel beading studies. Each new compound shows distinct pH response; however, our expectations were met as our original benzoic acid modified product still holds the most desirable degradation profile.
subject
Alginate
Alkylsilane
drug delivery
Molecular electronics
para substituted benzalkylsilanes
polymeric drug delivery
contributor
Welker, Mark E (committee chair)
Comstock-Ferguson, Lindsay R (committee member)
Lukesh, John C (committee member)
date
2022-05-24T08:36:10Z (accessioned)
2022 (issued)
degree
Chemistry (discipline)
embargo
2024-05-23 (terms)
2024-05-23 (liftdate)
identifier
http://hdl.handle.net/10339/100760 (uri)
language
en (iso)
publisher
Wake Forest University
type
Thesis

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