本論文分兩分，第一部分為延伸π共軛系統的七螺旋烴，第二部分為含取代基二炔化合物親電環化反應的討論。第一部分中，以實驗室內合成出的四苯并[f,i,o,r]七螺旋烴1做為參考，試著以簡化合成反應途徑為目的修正反應條件。將關鍵的中間物5,8-二碘-6,7-二苯基苉11透過鈀金屬催化的耦合反應分別得到經去羧化的含二甲基的四苯并七螺旋烴2，以及延伸螺旋烴π共軛系統的二苯并[i,o]二菲并[f,r]七螺旋烴3。並做晶體結構的比較，其中因結構中螺旋烴的互相影響造成化合物3的分子間距離為3.84 Å (化合物2為3.55 Å)，分子內螺旋烴末端苯環距離為3.63 Å (化合物2為4.03 Å)。在吸收光譜上，π共軛系統的延伸使化合物3的最大吸收波長為435奈米，比化合物2紅移了約37奈米(為398奈米)，也使得化合物3有最小的能隙值為2.70電子伏特(化合物2為2.77電子伏特)。電化學性質分析中，化合物2和3的HOMO能階值為–5.45和–5.48電子伏特，但沒發現還原電位，所以LUMO能階值由光物理性質得到的能隙值推算。
第二部分中將討論電子及立體效應在二炔三聯苯化合物中對親電環化反應路徑的影響。在含氟及含異丙基的例子中，氫譜和二維光譜圖經判斷後是沒有重排反應的發生，而含二甲基的化合物在氫譜中是明顯的不對稱訊號，加上晶體結構的確認是重排結構，初步推測可能在電子效應影響下造成重排，然而正確的反應路徑目前還不清楚，實驗仍在進行中。

This thesis is divided into two parts. In the first part, the syntheses, structures and properties of π-extended heptahelicene 2 and 3 were presented. Secondly, the mechanistic study of diiodo-molecules 11 and 6 were investigated in the following part.
In the first part, targeted molecules 2 and 3 were prepared from the key intermediate 11 using palladium-catalyzed reaction conditions. The structural analyses of compound 2 and 3 with single X-ray crystallography revealed that structural distortion of compound 3 resulted in the further intermolecular distance (2 and 3 were 3.55 and 3.84 Å, respectively) and shorter distance of extremities (2 and 3 were 4.03 and 3.63 Å, respectively) than compound 2. The longest wavelength absorption of 2 and 3 were observed at 398 and 435 nm, respectively. And the extension of π system in 3 performed not only in longer wavelength but in smaller HOMO-LUMO energy gap, which was determined to be 2.70 eV (2 was 2.77 eV). The HOMO values studied from cyclic voltammetry of 2 and 3 were –5.45 and –5.48 eV, respectively.
In the second part, the iodonium-mediated electrophilic cyclization reactions of terphenyl 21 were studied. A series of central benzene substituted terphenyl 21 were prepared. The formation of C13, C14 substituted picene were observed when isopropyl and difluoro were used whereas benzo[c]chrysene derivative was formed when dimethyl was used as substituent. The reason was proposed to be either electronic or steric effect. The more detailed studies are still working.

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