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Title: 'Click-fluors' : boronic acid-based saccharide sensors via CuAAC reaction
Author: Zhai, Wenlei
ISNI:       0000 0004 6057 3177
Awarding Body: University of Birmingham
Current Institution: University of Birmingham
Date of Award: 2017
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A series of mono- and bis-boronic acid compounds were synthesised via copper-catalysed azide-alkyne cycloaddition (CuAAC) reactions. The conditions of the CuAAC reaction were optimised across a range of substrates. In chapter 2, the saccharide binding capacity of the synthesised mono-boronic acids (1\(^s\)\(^t\) and 2\(^n\)\(^d\) generation "click-fluors") were studied by fluorescence spectroscopy and isothermal titration calorimetry (ITC). The fluorescence studies of the synthesised boronic acids binding with D-fructose indicated that the triazole ring - boron acid distance has an obvious effect on the fluorescence response. The binding model of mono-boronic acids and D-fructose was investigated through \(^1\)H and \(^1\)\(^1\)B NMR titrations. In chapter 3, study of the synthesised bis-boronic acid "click-fluors" showed the glucose binding affinity was improved by introducing an additional boronic acid group. Reducing the distance between two boronic acids was proven to be the key to achieve glucose selectivity. As a result, a fluorescent glucose selective bis-boronic acid sensor was successfully synthesised. In chapter 4, a preliminary study was carried out as a proof-of-concept experiment of templated synthesis of glucose-selective sensors using "click chemistry".
Supervisor: Not available Sponsor: China Scholarship Council ; University of Birmingham
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry