中文摘要

　　本研究主要是想利用薁類雙極性特性，合成薁類羧酸化合物，使其吸附在銀的表面上，以作為自組裝有機單層分子薄膜的材料。
首先由起始物 2-對甲苯磺醯氧□酮 (p-toluenesulfonyloxy-tropone)合成薁的中間物(8-羥基-2-氧-2H-環庚[b]呋喃-3-羧酸甲酯,methyl 8-hydroxy-2-oxo-2H- cyclohepta[b]furan-3-carboxy-late)，再與不同碳數的溴烷反應使其8位置接上長碳烷氧鏈，合成17個新產物，8-正烷氧基-2-氧-2H-環庚[b]呋喃-3-羧酸甲酯(methyl 8-n-alkoxy-2-oxo-2H-cyclohepta [b]furan-3-carboxylates)，再和乙醛、二乙胺反應合成17個薁類新產物，4-正烷氧基-1-羧酸甲酯薁類(methyl 4-n-alkoxy-azulene-1- carboxy-lates)。最後經過水解合成17個最終產物4-正烷氧基-1-羧酸類薁(4-n-alkoxy-azulene-1-carboxylic acids)。

Abstract

Making use of the dipolar property of azulenes, we synthesize 4-n-alkoxy-azulene-1-carboxylic acids as the material for self- assembled monolayer on silver surfaces.
We start with p-toluenesulfonyloxytropone to synthesize the inter- mediate of azulene (methyl 8-hydroxy-2-oxo-2H-cyclohepta[b]furan-3- carboxylate ) and on its 8-position carbon we attach to it a long alkoxy chain through reaction with different alkyl bromides. We now have 17 new products ( methyl 8-n-alkoxy-2-oxo-2H-cyclohepta[b]furan-3-carboxy- lates ). These are then reacted with diethylamine and acetaldehyde to get 17 azulene products ( methyl 4-n-alkoxy-azulene-1-carboxylates ). Finally after hydrolysis we are successful in synthesizing seventeen 4-n-alkoxy-azulene-1-carboxylic acids.

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