Oligo(m-phenylene)acetonylene:Sequential ROMP and Claisen Condensation of Norbornene Derivatives

• Main Authors: Te-Chung Wei, 魏德忠
• Other Authors: Tien-Yau Luh
• Format: Others
• Language: zh-TW
• Published: 2013
• Online Access: http://ndltd.ncl.edu.tw/handle/87267813868188199728

碩士 === 國立臺灣大學 === 化學研究所 === 101 === This thesis describes the sucessesful sequential polymerization of a monomer containing two different polymerizable groups, which can undergo polymerization under different conditions. N-arylpyrrolidine-fused norbornene connected with m-phenylene diacetate moiety is chosen as the starting monomer. This monomer contains norbornene group which can undergo ring-opening metathesis polymerization (ROMP) under various conditions to give well-defined single-stranded polynorbornene skeletons. This polynorbornene backbone can then serve as a template to control Claisen condensation reaction of m-phenylene diacetate moieties to afford the corresponding β-keto ester. This protocols is executed and unsymmetrical ladderphanes are obtained with different degree of polymerization. After hydrolysis under basic conditions, oligo(m-phenylene)acetonylenes with control molecular weight and narrow polydispersity index (PDI) are obtained. It is noteworthy that Claisen condensation of m-phenylene diacetate moiety without templation generated corresponding oligo(m-phenylene)acetonylene with uncontrolled molecular weight and polydispersity index (PDI). Key words: ROMP; Templated polymerization; Sequential polymerization; Norbornene; Oligo(m-phenylene)acetonylene