Novel oligodeoxyfluoroside derivatives - sub-nanometer fragments of graphene assembled on DNA, and a DNA-based photoswitch
Abstract/Contents
- Abstract
- This thesis describes the design and creation of novel Oligodeoxyfluorosides (ODFs), which are assemblies of fluorescent chromophores held together by DNA backbone. In the first chapter, we showcase our DNA-based carbon dots, which are made from sub-nanometer fragments of graphene assembled on the DNA backbone. These polyaromatic hydrocarbon stacks fluoresce in a wide range of colors spanning the visible spectrum, and were demonstrated to be useful for the multi-chromatic bioimaging of live cells, requiring only single wavelength excitation for multiplex imaging. These carbon dot mimics were found to exhibit most of the properties of carbon dots, and constitute an unprecedented 'bottom-up' approach to synthesizing low polydispersity carbon-dots with precisely known chemical structures. In the second chapter, we investigate the mechanism of a unique photoswitchable bisphenylalkynylpyrene containing ODF sequence, SSVV, that was found in a previous study to change emission color from green to blue upon UV irradiation. We propose a UV induced [2+2+2] cyclization of the bis-alkyne moiety with ambient oxygen as the origin of the color-change reaction, in which spatial separation of stacked pyrene units cause selective loss of excimer emission. In the third chapter, we investigate the effect of ODF sequence length on their optical properties and analyte sensing abilities. The emission profiles of ODFs are known to be sensitive to their immediate chemical environments, and have been utilized in previous studies for fluorescence sensing of varied analytes. Our study found diminished quantum yields as ODF sequence length increases, and no enhancements to the emission response on analyte exposure with longer sequences. Our fourth and final chapter describes our attempt to utilize the DNA backbone for the controlled assembly of Aggregation Induced Emission (AIE) dyes, with the expectation that we could elicit the AIE effect in a precise manner by varying the number of dye stacked against each other. However, this approach to realizing AIE was largely unsuccessful. Also included is a preface chapter containing an introduction to Oligodeoxyfluorosides, and summaries to each of the aforementioned chapters.
Description
| Type of resource | text |
|---|---|
| Form | electronic; electronic resource; remote |
| Extent | 1 online resource. |
| Publication date | 2017 |
| Issuance | monographic |
| Language | English |
Creators/Contributors
| Associated with | Chan, Ke Min Roy |
|---|---|
| Associated with | Stanford University, Department of Chemistry. |
| Primary advisor | Kool, Eric T |
| Thesis advisor | Kool, Eric T |
| Thesis advisor | Boxer, Steven G. (Steven George), 1947- |
| Thesis advisor | Santiago, Juan G |
| Advisor | Boxer, Steven G. (Steven George), 1947- |
| Advisor | Santiago, Juan G |
Subjects
| Genre | Theses |
|---|
Bibliographic information
| Statement of responsibility | Ke Min Roy Chan. |
|---|---|
| Note | Submitted to the Department of Chemistry. |
| Thesis | Thesis (Ph.D.)--Stanford University, 2017. |
| Location | electronic resource |
Access conditions
- Copyright
- © 2017 by Ke Min Roy Chan
- License
- This work is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported license (CC BY-NC).
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