本論文是以合成cycloiptycene分子1為目標，並希望利用化合物1的羥基形成分子間氫鍵來進行分子自我組裝，以形成有機奈米管。 我們設計出四種合成cycloiptycene分子1前驅物化合物4a的可能方法。方法一易產生其他異構物且純化的難度較高。方法二根據文獻必須在封管下反應方能進行，執行上較不易。所以本論文試圖以方法三及方法四合成化合物4a 方法三以化合物6與化合物12為起始物進行反應，我們成功的合成出化合物22a，但化合物22a與正丁基鋰及呋喃反應時沒有產生預期之化合物23a。可能原因是正丁基鋰與化合物22a上的酮基進行加成反應。 方法四以化合物6與化合物14為起始物進行反應，成功的合成出化合物29a，化合物29a與甲苯、過氯酸及乙醇反應後沒產生預期的化合物4a。 In this thesis, we take advantage of compound 1 to design organic nanotube. We would like to use the intermolecular hydrogen bonding to treat molecular self-assembled. Target compounds were prepared based on the Deils-Alder reaction. We have designed four kinds of strategy for synthesizing compound 4a. Method Ⅰis more difficult purification and easily produces isomers. Method Ⅱ must be in hard condition. So we use method Ⅲ and Ⅳ to synthesize compound 4a. We synthesize the compound 22a successfully in method Ⅲ. But we don’t get compound 23a by compound 22a reacting with n-butyl lithium and furan. We synthesize the compound 29a successfully in method Ⅳ. But we don’t get compound 4a by compound 29a reacting with perchloric acid, toluene and ethanol.
