環辛四烯(cyclooctatetraene)是環辛烷之不飽合衍生物，沒有額外官能基修飾時呈現非平面性結構，儘管其鍵長差異交錯明顯，但由於結構的非平面性，整體的反芳香性受到限制，先前研究顯示，環辛四烯的兩面角越小，HOMO-LUMO能隙會縮減，進而提升其反芳香性，並且具有作為有機半導體的潛力。
因此，我們期望在環辛四烯上下接上已知合成路徑的聯伸二苯並在左右以乙烯橋銜接，以提升其結構的平面性。在這個基礎上，我們嘗試多種的合成路徑，最終成功合成出具有八元環結構化合物28a、28b，但在合成左右兩邊的乙烯橋卻遇到瓶頸，目前推測因其易受氧化的特性，導致無法順利得到化合物33a、33b。
在本論文中，我們使用理論計算分別模擬出化合物28a、28b、33a及33b的最佳化結構，並且透過HOMA值與NICS值來鑑定各個結構的反芳香性。
我們最終成功合成出化合物28a、28b，在未來的合成過程中，可以藉由本論文得出的結果去進行後續的研究及應用，期許未來能測試出化合物33a及33b的最佳合成路徑。

Cyclooctatetraene is an unsaturated derivative of cyclooctane. It has a non-planar structure. Although its bond lengths alternate significantly, its overall antiaromaticity is restricted due to its non-planar structure.
Therefore, we aimed to enhance the planarity of the structure by functional group modifications. We successfully synthesized compounds 28a and 28b, which have an eight-membered ring structure. However, trying to synthesize compounds 33a and 33b encountered bottlenecks likely due to their susceptibility to oxidation.
We successfully synthesized compounds 28a and 28b and through the theoretical calculation identified the antiaromaticity of each compound. In future synthesis processes, we can use the results obtained in this thesis to conduct further research and applications, with the aim of identifying the optimal synthesis route for compounds 33a and 33b.

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