In this project, 4-bromobenzamide di-substituted perylene diimide (PDI-BA-1) was synthesized and investigated by solvent-, concentration- and temperature-dependent studies. Controllable self-assembly behaviour and morphologies were observed by ultraviolet-visible-near infrared absorbance spectrometry (UV-Vis) and transmission electron microscopy (TEM), providing a ground for further investigation of formation of supramolecular polymers. Solubilities of PDI-BA-1 in fourteen solvents were evaluated by Hansen solubility parameters (HSP). A relationship between solvent HSP and self-assembly behaviour of PDI-BA-1 was proposed. By tuning the hydrogen-bonding component and dipolar cohesive component of HSP (δH, δP), controllable self-assembly behaviour was observed in the ethyl acetate/n-hexane dual-solvent system. A set of computational methods were studied for monomeric PDI-BA-1 geometry optimization and excitation behaviour. Two critical conformers of PDI-BA-1 (reactive-open and trapped-closed) regarding controllable inter-/intra-molecular hydrogen bonds were found and optimized. To further explore functional supramolecular perylene diimide derivatives, a preliminary synthesis and modelling work of tetra(aniline)-substituted perylene diimide (TANI-PDI) was started, which lays the groundwork for further studies in the future.
Date of Award | 21 Jan 2021 |
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Original language | English |
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Awarding Institution | - The University of Bristol
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Supervisor | Charl F J Faul (Supervisor) |
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Investigation of Perylene Diimide Functional Supramolecular Polymers
Fang, X. (Author). 21 Jan 2021
Student thesis: Master's Thesis › Master of Science (MSc)