多並苯醚類化合物的合成與多並苯醚類化合 物於自組裝分子薄膜之研究

The Synthesis of Acene Ethers and Sulfides and Application of Such Compounds in Constructing Self-Assembly Monolayer

柳逸軒(Yi-Shiuan Liou)

指導教授 ： 侯敦仁 ； 林質修

國立中央大學/理學院/化學系/碩士(2006年)

摘要

摘要

本篇論文目標為合成多並苯醚類化合物，並且利用這些化合物於自組裝分子單層薄膜的研究。除了沿用本實驗室之前開發的酸催化醚類交換反應外，並開發用於不同取代位置交換反應的新條件，更進一步將此策略延伸至四並苯化合物。經交換反應所得的蒽與四並苯硫醚30, 52等化合物可繼續進行retro-Micheal反應產生硫陰離子並進一步官能化。所得的硫酯化合物目前無法成功的用於自組裝分子薄膜建構，期待未來以硫腈或其他官能基吸附方式完成此一目標。

關鍵字

多並苯化合物 ； 蒽 ； 四並苯 ； 醚類交換反應

並列摘要

Abstract

The major goal of this thesis is to synthesize acene ethers and sulfides and employ these compounds for the construction of self assembly monolayer (SAM). Continuing our “acid catalyzed ether-ether and ether-sulfide exchange” protocol, we synthesized a range of substituted anthracene derivatives. We then extended this methodology to tetracenes derivatives. Compounds like 30, 52 thus obtained can undergo retro-Micheal reaction to generate thiolate anions in situ and further functionalized. A variety of anthracene and tetracene thioester derivatives were obtained with such strategy. However, we have not been successfully using these thioesters in SAMs construction at present. From other’s preliminary result, we expect thiocyanide to be another suitable option in such pursuit.

並列關鍵字

ether exchange reaction ； acene ； anthracene ； tetracene

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