螺旋烴 (helicene) 為相鄰之芳香環透過稠合而形成的一種非平面多環芳香烴化合物，其結構中之螺旋特性可被應用在不對稱催化合成上；此外，由於苯環螺旋之旋轉方向所產生左旋及右旋兩種不同圓偏振光之特性，更使其能被廣泛應用於有機電子材料及有機發光材料上。
本論文以苉作為主體，利用螺旋烴之結構來進行π-共軛系統之延伸。首先，在合成路徑之設計上，以碘苯化合物 37作為前驅物，透過親核加成反應及傅里德-克拉夫茨反應成功合成出[9]螺旋烴化合物 40、43；但在利用碳氫活化的方式增加苯環數量以建構[9]螺旋烴化合物 45、48的嘗試上，並未順利達成；此外，在利用氧化脫氫反應進行化合物 41之合成的嘗試上，也因雙自由基性質過高而無法順利合成。其次，本論文亦透過X-ray單晶繞射來進行化合物 40之結構鑑定及扭轉角和芳香性的分析；由所得晶體數據發現到：具有螺旋結構之化合物 40呈現不對稱之構型，螺旋相對應處之扭轉角皆不同，但結構中苯環之芳香性並未因此遭到破壞。
展望未來，可嘗試藉由本論文合成出來之化合物 40、43進行五員環上官能基之修飾，以利[9]螺旋烴化合物π-共軛系統之延伸。

Helicene is one kind of non-planar polycyclic aromatic hydrocarbons formed by ortho-fused aromatic rings. The helical structure and chirality properties make it possible to have wide applications in the synthesis of asymmetric catalysis, organic electronic materials and organic light-emitting materials. In this thesis, tetrabenzo[9]helicene derivatives were prepared and their properties were studied. The synthetic routes of compound 40 and compound 43 started with the nucleophilic addition of diiodo-precusor 37 to the corresponding electrophiles and subsequent Friedel-Crafts alkylation. The following oxidative dehydrogenation generated of compound 41 was not successful because of its instability under ambient conditions. The structure characterization, and the analyses of twisted properties and aromaticity of compound 40 were also conducted by X-ray crystallography study. The result showed that, while having asymmetric structure, the aromaticity of compound 40 was not affected. Several attempts to prepare π-extended derivatives compound 45 and compound 48 the palladium catalyzed C-H activation of compound 37 was utilized as the key step. Unfortunately, the desired products compound 45 and 48 were not obtained, presumably due to the steric hindrance of adducts. In the future studies, it might be tried to change the functional group on five-membered rings of compound 40 and 43 to extend the π-conjugated system of helicene.

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