Synthesis of Novel Reactive Polymers Having Oxirane Structure in the Main Chain by Polycondensation of Bis(sulfonium ylide) with Dialdehyde

Abstract

Poly(phenylenevinylene oxide)s (PPVOs) having oxirane groups in the main chain were prepared by the Corey–Chaykovsky reaction between bis(sulfonium ylide)s and dialdehydes. The sulfonium ylide formed in situ from m-xylylenebis(dimethylsulfonium perchlorate) by the use of lithium diisopropylamide (LDA) as a base was reacted with terephthalaldehyde to afford m,p-PPVO with Mn=3600. Oxirane groups in PPVO were successfully reacted with various reagents such as acetic acid, lithium aluminum hydride and n-octylamine to give the corresponding ring-opening products. The properties of the ring-opened polymers reflected the structure of the reagents used for the polymer reactions. These results showed that PPVOs are novel reactive polymers whose properties can easily be adjusted by polymer reactions.