荑分子具有三維空間性質且結構剛硬，研究發現這類分子具有多樣的應用性，例如三苯荑或五苯荑在分子的建構上已被廣泛的應用，這類型分子不論是在基礎的研究或是實際的應用都有一定的重要性，目前已經有很多合成荑分子的相關報導，但由於荑分子具有很高的對稱性質，因此要對於荑分子苯環進行高區域選擇性反應及精確的化學計量控制是較為困難。儘管在近幾年來對於荑醌分子的合成已經有顯著的發展，但將荑醌分子更進一步的官能化卻幾乎沒有什麼發展，為了促進五苯荑分子與荑分子化學一樣能有更廣泛的應用，因此需要研發能簡單合成新型荑分子的方法。本篇論文的目標為合成不同的五苯荑官能基，首先利用五苯荑醌為起始物，進行一系列中心苯環官能化反應，反應過程中利用去胺基反應、鹵化反應、烷化反應、氰化反應以及還原反應來合成我們的目標物，其中一邊的取代基包括了胺基、重氮鹽基、硝基、氯基、溴基、碘基、氰基及醛基，另一邊取代基為氫、羥基、辛氧基以及全氟丁基磺酰氧基，我們認為這些具有不同取代基的五苯荑分子將有潛力被應用在相關的五苯荑系統上。

The three-dimensional rigid iptycene frameworks such as triptycene and pentiptycene have found versatile usages in constructing molecules of both fundamental and practical importance. While the synthesis of many parent iptycenes is well-documented, further functionalization of their phenyl rings with both high regioselectivity and precise control of stoichiometry appears to be rather difficult in view of their high molecular symmetry. Although significant progress in the synthesis of more extended iptycene quinones has been made in the past years, transformation of these quinones to functionalized iptycenes has been poorly developed. To expedite the pentiptycene as well as larger iptycene chemistry, methodologies for facile synthesis of new iptycene building blocks are highly demanded.
This thesis is aimed to develop efficient methodologies for the synthesis of new middle-ring monsubstituted or disubstituted pentiptycenes from pentiptycene quinones. We have successfully used deamination, halogenation, alkylation, cyaniding, and reduction reactions to prepare our target compounds. One of the substituents is a amino, diazo, nitro, chloro, bromo, iodo, cyano, or formyl group and the other is a hydrogen, hydroxy, alkoxy, or perfluoro-1-butane sulfonyloxy group. These functionalized pentiptycenes are potential building blocks for constructing novel pentiptycene-incorporated systems.

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