系列一: 六苯并蔻衍生物設計之合成探討與其物理性質之研究；系列二: 引入鹵素原子具偶極矩之板形與盤形分子探討

seriesI: Design, synthesis discussions and physical properties of hexabenzocoronene derivatives studies; series II: Dipole of the board and disc like molecular introduce fluoro substituent studies

林韋志(Wei-Jhih Lin)

指導教授 ： 徐秀福

淡江大學/理學院/化學學系碩士班/碩士(2015年)

https://doi.org/10.6846/TKU.2015.00261

摘要

大多數的六苯并蔻衍生物 (hexabenzocoronenes, HBCs)具有筒型液晶相，但澄清點溫度偏高，升溫至澄清點溫度後會有熱裂解的現象產生，因此無法升溫至澄清點溫度後再降溫而使分子有效的排列，本論文系列一利用引入氟取代基具烷氧鏈的策略，藉由改變氟取代基的數目與苯基上單鍵旋轉，使得六苯基苯 (hexaphenylbenzenes，HPBs)經由氧化環化脫氫反應後，產生不同異構物，希望利用異構物之間共存，可望達到降低澄清點溫度的目的，此外引入氟原子也可改變其物理性質。
系列二將已發表文獻之分子加以修飾，則是在苯環中心核上引入鹵素原子 (如: 氟、氯等)，造成分子中心具有局部偶極矩產生，可望誘導出雙光軸向列相液晶之形成。合成出的化合物皆無液晶相，利用偏光顯微鏡、熱微差掃描儀鑑定其性質。

關鍵字

六苯并蔻 ； 六苯基苯 ； 氧化環化去氫反應 ； 異構物 ； 板形分子 ； 盤形分子 ； 氟原子

並列摘要

The well-known organic semiconducting alkyl hexabenzocoronenes (HBCs)exhibited columnar phases with high clearing temperature by thermal decomposition. In this thesis fluoroalkoxyphenylethyne was used for the preparation of hexaphenylbenzenes (HPBs) which can be cyclized to HBCs. Due to the rotational of side-arms in HPBs, various isomeric forms are expected when the HPBs are cyclized into HBCs. The coexistence of various isomers of HBCs should lead to significantly lower clearing temperatures for practical device fabrications. Moreover, the introduction of fluoro substituents is expected to impose physical property changes.
the compound of paper was modified in part two. The central core was introduced halogen, such as fluorine, chlorine. The molecular lead to local dipole in the central core. We expected to intramolecular packing to give a biaxial nematic mesophase. The compound was synthesis sucessfully in the thesis, but no one is liquid crystal phase. Use polarizing optical microscopy (POM) and differential scanning calorimetry (DSC) to measure its properties.

並列關鍵字

hexa-peri-hexabenzocoronenes ； hexaphenylbenzenes ； oxidative cyclodehydrogenation ； isomeric ； board-like ； disc-like ； fluorine.

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