Synthesis and characterization of unsymmetrically substituted fenestrindane derivatives

In this thesis, the synthesis and characterization of various types of unsymmetrically substituted fenestrindane-based non-planar polycyclic aromatic compounds (PAC) were reported. Selective functionalization plays a determining role in the synthesis. Further application of these unsymmetrically substituted fenestrindane derivatives were attempted. The structure and properties of these novel molecules would be studied by various techniques including proton and carbon NMR spectroscopy, mass spectrometry, X-ray crystallography, UV–vis spectroscopy, fluorescence spectroscopy and cyclic voltammetry.Chapter 1 reviewed the chemistry of Fenestrindane and its derivatives, including the synthesis, functionalization and characterization.Chapter 2 introduced various example of linkage reaction which joins two or more single molecule to form a single large molecule. These examples were introduced and classified by the linker.Chapter 3 outlined the research plan and the design approach. The synthesis and characterization of the unsymmetrically substituted fenestrindane-based PACs were reported. The selective functionalization on the fenestrindane core was investigated.Chapter 4 discussed the oligomerization of unsymmetrically substituted fenestrindane-based PACs by different reactions.Chapter 5 summarized the thesis and gave an outlook of research outcome of this thesis.Chapter 6 mentioned the experimental details of all new compounds, the followings were included: the synthetic procedure, yield, melting point, 1H NMR data, 13C NMR date and mass data.This thesis demonstrated the selective functionalization on the fenestrindane core and the synthesis of oligomer based on the unsymmetrically substituted fenestrindane-based PACs. The research outcome paved the way for further research on synthesis of various types of oligomer based on unsymmetrically substituted fenestrindane-based PACs.本論文報道一系列不對稱海灣橋聯窗茚滿衍生物之合成及表徵。合成過程中，選擇性功能化扮演不可或缺的角色，它將對稱海灣橋聯窗茚滿衍生物轉變為不對稱。而不對稱海灣橋聯窗茚滿衍生物將進一步應用，以組成二聚體和四聚體。這些新穎分子的結構會使用不同技術進行分析，技術包括質子及碳-13 核磁共振光譜法、質譜法、 X-射線晶體學 、 紫外–可見分光光度法 、 螢光光譜法和循環伏安法。第一章述說了海灣橋聯窗茚滿及其衍生物的化學，包括其合成過程、功能化和表徵。第二章介紹了不同的化學合成反應例子，這些反應能用於由兩個以上的單體和連繫分子產生成二聚體和四聚體。這些反應會依連繫分子類型而分類。第三章勾勒了整個研究計劃和設計思路。不對稱海灣橋聯窗茚滿衍生物的合成和表徵亦紀錄在此。當中，選擇性功能化亦會深入討論。第四章討論不對稱海灣橋聯窗茚滿衍生物和不同連繫分子的低聚合反應。不對稱海灣橋聯窗茚滿衍生物的聚合物的合成和表徵亦紀錄在此。第五章綜合了這份論文及提出不同的研究方向。第六章提及所有新不對稱海灣橋聯窗茚滿衍生物的實驗詳情，包括合成過程、產率、熔點、質子及碳-13 核磁共振光譜和質譜。本論文展示了對稱海灣橋聯窗茚滿衍生物的選擇性功能化及建基於不對稱海灣橋聯窗茚滿衍生物的低聚合反應。這些研究結果為未來的不對稱海灣橋聯窗茚滿衍生物的低聚合反應提供了寶貴經驗。Lau, Wing Wa."October 2020."Ph.D. Chinese University of Hong Kong 2021.Includes bibliographical references (leaves 130-135).Abstracts also in Chinese.Title from PDF title page (viewed on November 04, 2022)