多並苯化合物簡易合成法之研究

Facile Synthesis of Acene Compounds

林義鈞(Yi-chun Lin)

指導教授 ： 劉行讓

國立清華大學/理學院/化學系/碩士(2006年)

摘要

多並苯化合物因其良好的光電性質，近年來在有機電子學的研究中佔
有重要的地位，但多並苯化合物的合成常因溶解度及穩定性的問題而面臨困境，本篇論文之目標即在於發展步驟簡單且反應條件溫和的多並苯合成法。所採用的合成方式以鄰位二丙炔醇為起始物，在鹼性環境中與次磺氯或亞磺氯作用生成丙二烯後，再經環化反應得多並苯化合物。首先藉由探討不同硫化物對產率的影響以推論反應的瓶頸步驟，並據之以進行反應最佳化。後以擇定之反應條件成功的合成多種四並苯衍生物與五並苯化合物，並對四並苯衍生物做光學性質測量。

關鍵字

多並苯 ； 四並苯

並列摘要

Owning to their excellent photoelectric properties, acenes have played an important role in the studies of molecular electronics. However, the synthesis of acene compounds is problematic because of their notoriously poor solubilities and stabilities. The major goal of this thesis is to develop a new synthesis of acenes under mild conditions and few operational steps. Using ortho-bis(porpargyl alcohol) derivatives as starting materials, we employed sulfenyl or sulfinyl chloride under base condition to generate bis-allene intermediates. And the intermediates underwent subsequent intramolecular cyclization and aromatization reactions to afford acene products. We optimized the reaction conditions based on our best understanding of the reaction mechanism. 23 tetracene and pentacene derivatives were obtained through this new method. Their photophysical properties are also studied.

並列關鍵字

acene ； tetracene

參考文獻

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