本篇論文提供八圈烯的反轉動力學行為分析，且成功合成一系列9,10-雙芳基取代菲類衍生物，探討其結構特性與芳基旋轉動力學行為。
全取代八圈烯及其非平面次結構的反轉動力學由理論計算探討，證實全取代八圈烯是經由假旋轉的方式進行翻轉，其能量為20.7千卡/莫爾，而其非平面次結構需要更多的能量進行結構翻轉。
本篇研究成功透過鈀金屬催化，將炔類與2-鹵聯苯化合物進行環合反應，得到一系列9,10-雙芳基取代菲類衍伸物，利用變溫氫核磁共振實驗探討其高溫下旋轉動力學行為，配合理論計算推測芳香環官能基翻轉機制，探討一系列不同取代基對結構與旋轉活化能的影響。研究結果發現，菲主體結構越扭曲、結構立體環境越擁擠，使得基態時位能較高，降低芳基旋轉所需能量。

In this thesis, the dynamic behavior of persubstituted[8]circulene (1) and its fragments (13, 14, 15, 16) are discussed base on theoretical calculations that are made using density functional theory (DFT). The ring flipping of persubstituted[8]circulene (1d) is confirmed to proceed through pseudorotation with a barrier of around 16.3 kcal/mol, whereas ring inversion of its nonplanar fragments requires much more energy. To elucidate the rotational behavior of their aryl substituents, the phenanthrene substructure (9,10-di(3-tolyl)-1,2,3,6,7,8-hexamethylphenanthrene, 10) was investigated. However, the measured barrier to the rotation of the aryl pendant group in 10 (16.3 kcal/mol) was smaller than 9,10-di(3-tolyl)phenanthrene 11 (20.3 kcal/mol) which is less twisted and uncrowded. Hence, the structural analysis and dynamic behavior of a series of 9,10-diarylphenanthrenes were studied. The syntheses, structural analyses and dynamic properties of highly substituted 9,10-diarylphenanthrenes were theoretically and experimentally investigated. Suitable substituents at critical positions in the phenanthryl framework formed a crowded and rigid backbone through peri repulsion and the buttressing effect. A twisted structure has a higher potential energy at ground state than does a planar phenanthrene, and so has a lower barrier to aryl rotation.

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