Conjugated Organic Molecules with Azide Moieties and Their Self-Assembled Nanospheres: Syntheses, Characterizations and Applications
Date Issued
2016
Date
2016
Author(s)
Shen, Chia-An
Abstract
In this research, we designed a highly fluorescent -conjugated organic molecule T3-4im-2Az with ionic self-assembly motifs and azide groups for further functionalization. The molecule spontaneously assembles into hollow vesicle-like nano-spheres with a diameter of ca. 200 nm in acetone solutions, which was characterized by electron microscope and dynamic light scattering. The copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition, which is commonly known as “click reaction”, was exploited to functionalize T3-4im-2Az to obtain the model compound T3-4im-2OH. We systematically investigated the self-assembly mechanism of T3-4im-2OH through the manipulation of non-covalent interactions by varying the solvent composition. In another experiment, we used the click reaction to incorporate T3-4im-2Az with a green fluorophore, which enables the product, T3-4im-2NI to possess intramolecular FRET ability. We expect to examine more deeply into the self-assembly mechanism of this system by measuring the FRET efficiency under different self-assembly conditions. For further application, we choose to use T3-4im-2Az incorporating with boronic acid moieties. Boronic acid is well-known to interact with diol functionalities, and as such, we examined the influences of dopamine and glucose on the newly synthesized T3-4im-2BA system. Before adding dopamine/glucose, T3-4im-2BA can self-assemble into intact nanospheres, which collapse upon the addition of dopamine/glucose. We look forward to the application of this system on dopamine/glucose sensing in biological systems.
Subjects
Self-Assembly
Click chemistry
Energy transfer
Diol
Type
thesis
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