The Study of Synthesis of 3-Alkyl-4-alkoxy-azulene-1-carboxylic acid in Mixed Self-Assembled Monolayer

• Main Author: 王慧娟
• Other Authors: 黃鑑玉
• Format: Others
• Language: zh-TW
• Online Access: http://ndltd.ncl.edu.tw/handle/98189485147572900204

碩士 === 國立新竹教育大學 === 應用科學系碩士班 === 97 === Making use of the dipolar property of azulene, we synthesize 3-alkyl-azulene-1-carboxylic acids, 4-alkoxy-azulene- 1- carboxylic acids and 3-alkyl-4-alkoxy-azulene-1-carboxylic acids as the material for self-assembled monolayer and mixed self-assembled on silver surfaces. we start with p-touenesulfonyloxytropone(B) to synthesize the intermediate of azulene, C and D (methyl 2-oxo -2H -cyclohepta[b] furan-3-carboxylate C and methyl 8-hydroxy- 2-oxo-2H- cyclohepta﹝b﹞furan-3-carboxylate D),and intermediate D has been reacted with 1-bromononane and 1-bromoheptadecane to accomplished methyl 8-nonoxy-2-oxo-2H-cyclohepta[b]furan- 3- carboxylate(E), and methyl 8-heptadecoxy-2-oxo-2H- cyclohepta [b]furan-3- carboxylate(F),and then reacted with diethylamine and acetaldehyde to accomplished methyl 4-nonyloxy-azulene- 1-carboxylate(I) and methyl 4-heptadecyloxy-azulene-1- carboxylate(J). we use dodecanal and isosanal reacted with morpholine to form enamine ,and then reacted with the compounds that the aforesaid compounds (C、E、F), to accomplished two 3-alkyl-azulene -1-carboxylates(G、H),and four different 3-alkyl-4-alkoxy- azulene -1-carboxylates(K、L、M、N). Finally after hydrolysis we are successful to get two 3-alkyl-azulene-1-carboxylic acids(O、P), two 4-alkoxy- azulene -1-carboxy acids(Q、R), and four 3-alkyl-4-alkoxy- azulene-1- carboxylic acids(S、T、U、V).