利用灣區雙喹啉做為架橋基建構多層苯基堆疊之梯狀化合物;Using Bay Area bisquinoline as a bridging unit to construct ladder compounds with multilayer phenyl stacking

Please use this identifier to cite or link to this item: http://ir.lib.ncu.edu.tw/handle/987654321/94771

Title:	利用灣區雙喹啉做為架橋基建構多層苯基堆疊之梯狀化合物;Using Bay Area bisquinoline as a bridging unit to construct ladder compounds with multilayer phenyl stacking
Authors:	歐書瑋;Ou, Su-Wei
Contributors:	化學學系
Keywords:	雙喹啉
Date:	2024-08-22
Issue Date:	2024-10-09 15:28:54 (UTC+8)
Publisher:	國立中央大學
Abstract:	本篇論文研究方法為利用鄰位胺基之苯酮作為起始物與1,4-環己二酮透過Friedländer 縮和反應形成雙喹啉，並以此做為架橋基將多層苯基堆疊的梯狀化合物。芳香堆疊結構造成許多有趣的物理性質微調，光學性質，又或者整個堆疊結構上的穩定，又或是自組裝的行為，都可以藉由π-π作用力所致的芳香堆疊結構產生；撇開科學領域，多層芳香堆疊對稱結構頗能啟發人們的美感，以上都是合成出多層芳香堆疊結構的動機。本文透過兩種主要合成策略去解決寡體合成上的難題，分別為利用末端單元 (terminal unit) 與當量數控制去解決，利用這兩種方法以建構出本篇計畫所需之建構單元，並於研究中發現此芳香堆疊結構系列之化合物皆出現不溶於多數溶劑且怕光的情形。最後成功合成出具有多層苯基堆疊且具對稱美感之化合物，其特殊的性質在研究上值得有更多的探討。 ;This paper′s research methodology involves using ortho-amino ketones as starting materials to react with 1,4-cyclohexanedione via the Friedländer condensation reaction to form bisquinoline. This bisquinoline is then used as a bridging unit to construct ladder-like compounds with multilayered phenyl stacking. The aromatic stacking structure leads to many interesting tunable physical properties, optical properties, stability of the entire stacked structure, or self-assembly behavior, all of which arise from the aromatic stacking structure induced by π-π interactions. Beyond the scientific realm, the multilayered aromatic stacking symmetric structures can inspire people′s sense of aesthetics, providing motivation for synthesizing such structures. This paper addresses the challenges in oligomer synthesis through two main synthetic strategies: using terminal units and controlling stoichiometry. These methods are employed to construct the necessary building blocks for this project. During the research, it was found that this series of aromatic stacking compounds are insoluble in most solvents and are photosensitive. Ultimately, compounds with multilayered phenyl stacking and symmetrical aesthetics were successfully synthesized, and their unique properties are worthy of further investigation.
Appears in Collections:	[Graduate Institute of Chemistry] Electronic Thesis & Dissertation

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