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Abstract : This thesis reports on the use of the element boron in organic chemistry. Its role in catalysis, as well as its broad utility when in the form of a boronic acid functional group is demonstrated. Boric acid and boronic acids have applications in numerous kinds of chemical reactions as catalysts. Boric acid is demonstrated in this work to catalyse the esterification of a- hydroxycarboxylic acid starting materials, including carbohydrates, typically in excellent yield. A series of reactions were conducted to demonstrate the utility and limitations of this technique. Included in this work is the synthesis of the carbohydrate, KDO. Furthermore, a series of esters were generated using salicylic acid as a starting material, one of which was subjected to x-ray crystallographic studies. Also in this thesis a novel type of boronic acid catalysed amide forming reaction is described. The reaction is shown to proceed rapidly under mild reaction conditions with little purification required to give a pure product. Structural identification of the amide products is discussed and hypothesised molecular configurations are presented. Fluorescence sensors are described as a practical application of boron {u2013} polyol interactions. Supporting theories are outlined and published work is summarised, compared and contrasted. The carbohydrates sialic acid and KDO are identified as molecular targets for boronic acid based fluorescence sensors. The benefits of multiple binding sites and optimised molecular geometry are clearly shown in the results of fluorescence assays. Sensor molecules reported in this thesis demonstrated selective binding to the carbohydrates, sialic acid and KDO.
An essential reference for any laboratory working in the analytical fluorescence glucose sensing field. The increasing importance of these techniques is typified in one emerging area by developing non-invasive and continuous approaches for physiological glucose monitoring. This volume incorporates analytical fluorescence-based glucose sensing reviews, specialized enough to be attractive to professional researchers, yet appealing to a wider audience of scientists in related disciplines of fluorescence.
In this dissertation, we established a new approach assisted by computational chemistry to design fluorescent sensors. The approach is applicable to predict the behavior of a fluorophore-bridge-receptor sensor based on photoinduced electron transfer (PET). Our first designed rhodamine based pH sensor exhibits strong fluorescence under acidic conditions and very weak fluorescence under basic conditions, just as the computations predicted.
Chapter 3 of this dissertation explores a hypothesis that leverages the seesaw photophysical model for N-aryl (2,3- and 1,8-) naphthalimides. The Heagy group initially developed this model to understand the dual fluorescence effect concerning the electron donor or electron-withdrawing substituents. This study envisions the design and synthesis of novel dual fluorescence molecules for a new class of N-aryl-phenanthridinone dyes. The applied photophysical model further investigates these dyes with a substitution pattern opposite naphthalimide systems. Interestingly, predictive computational modeling shows that the substituent pattern, used previously for 2,3-naphthalimides, relies on these groups getting placed on rings in opposite positions for N-aryl-phenanthridinones. Chapter 4, provides an overall conclusion of the and future directions for both parts of the research. In chapter 5, a complete description of experimental data is provided for the characterization of all the dye systems presented. This data includes a detailed synthesis procedure, characterization, purity analysis by HPLC, absorptivity calculation, fluorescence lifetime measurements, quantum yield determination, biological evaluation and fluorescence titration.