Towards arylene-ethynylene based supramolecular hosts
department or school: Science, Faculty of
department or school: Chemistry, Department of
data provider: DSpace
degree campus: UBCV
creator: Le, Debbie
issued: 2019-04-17T16:34:42Z
issued: 2019
related degree: Master of Science - MSc
degree grantor: University of British Columbia
description: Motivated by the pursuit of shape-persistent macrocycles that could act as hosts for metal ions or clusters, we set out to construct arylene-ethynylene macrocycles with functionalized interiors. A step-wise synthesis using Sonogashira cross-coupling and deprotection reactions was used to make a series of arylene-ethynylene molecules. These compounds included a macrocycle with interior methoxy functional groups and trimers with methoxy or amine functionalities. These molecules were characterized using NMR spectroscopy as well as ESI-TOF mass spectrometry. The synthesis of these molecules provides the groundwork for the development of new aryleneethynylene based receptors to be used in host-guest chemistry.
aggregated CHO: https://circle.library.ubc.ca/rest/handle/2429/69747
note: Towards arylene-ethynylene based supramolecular hosts by Debbie Le B.Sc., Simon Fraser University, 2014 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE in THE FACULTY OF GRADUATE AND POSTDOCTORAL STUDIES (Chemistry) THE UNIVERSITY OF BRITISH COLUMBIA (Vancouver) April 2019 © Debbie Le, 2019 ii Abstract Motivated by the pursuit of shape-persistent macrocycles that could act as hosts for metal ions or clusters, we set out to construct arylene-ethynylene macrocycles with functionalized interiors. A step-wise synthesis using Sonogashira cross-coupling and deprotection reactions was used to make a series of arylene-ethynylene molecules. These compounds included a macrocycle with interior methoxy functional groups and trimers with methoxy or amine functionalities. These molecules were characterized using NMR spectroscopy as well as ESI-TOF mass spectrometry. The synthesis of these molecules provides the groundwork for the development of new arylene-ethynylene based receptors to be used in host-guest chemistry. iii Lay Summary Nature relies on enzymes to facilitate important processes such as photosynthesis and cellular metabolism. Inspired by the many enzymes that contain both molecular and metallic subunits, we sought to design and produce chemical complexes with organic and inorganic components. Here, we describe the synthesis of new molecules that can be used to form structures with metal atoms. Such complexes may act as minimalist models of the many metal-containing proteins found in nature to provide insight into how these proteins or enzymes work. These compounds may also have valuable applications in improving the efficiency of chemical reactions that are already used in industry. iv Preface This dissertation is my original, unpublished work. I conducted all the experiments for this thesis and all my work was carried out under the guidance of my supervisor, Prof. Mark J. MacLachlan. v Table of Contents Abstract ....…
has type: Thesis/Dissertation
date issued: 2019-05
is shown at: 10.14288/1.0378289
language: eng
degree discipline: Chemistry
provider: Vancouver : University of British Columbia Library
publisher: University of British Columbia
rights: Attribution-NonCommercial-NoDerivatives 4.0 International
rights URI: http://creativecommons.org/licenses/by-nc-nd/4.0/
scholar level: Graduate
type: Text
identifier URI: http://hdl.handle.net/2429/69747