本論文期望透過一簡單的合成方法，在低溫的條件下合成具有四員環結構的聯伸二苯 (biphenylene, 1)之衍生物，並進一步合成苯并環丁聯伸二苯衍生物P1與苉衍生物P2。
第一部分為苯并環丁聯伸二苯的合成探討，利用有機全合成方法，成功合成出多環芳香烴苯并[3,4]環丁[1,2-b]聯伸二苯衍生物26。利用鹵化三聯苯作為起始物，在低溫下與強鹼的交換後，經由生成苯炔中間體進行分子內環化，經由雙邊的環化後，生成直線型的苯并環丁聯伸二苯衍生物26，並進一步嘗試藉由薗頭耦合反應合成出苯并[3,4]環丁[1,2-b]聯伸二苯巨環衍生物30。
第二部分是苉衍生物的合成探討，目標利用有機全合成的方式得到苉衍生物P2。雖然本論文成功利用簡單的條件合成出前驅物5,8-二碘-6,7-雙(2,4,6-三氟苯基)苉 (35)，但隨後嘗試使用相同方式合成具有四員環結構的苉衍生物之環化反應中，反應結果不如預期，所以要如何找到適合條件將關鍵步驟之化合物35成功合環，是將來繼續發展的重點。

A novel synthesis of [3]phenylene and picene derivatives was developed under mild reaction conditions. In 2017, our group reported a simple method for the preparation of biphenylene derivatives via intramolecular cyclization of in-situ generated benzyne intermediate.
In part I, a synthetic strategy for the preparation of [3]phenylene derivative 26 was performed using a easily accessible haloterphenyl as the starting material. The optimized reaction conditons are established using t-BuLi as a organolithium agent and ether as the solvent. We also attempted to prepare [3]phenylene derivative 30 using Sonogashira coupling reaction. However, this synthetic procedure is still under investigation.
In part II, we attempted to synthesize picene derivative P2. We used five steps to synthesize the precursor of 36, 6,7-bis(2-chloro-4-fluorophenyl)-5,8-diiodopicene (35). However, the following intramolecular cyclization was unsuccessful under optimized reaction conditions. Presumably, compound 36 is too stable to generate benzyne intermediate.

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