Physical Sciences and Mathematics Commons^™

Alkyne Metathesis With Simple Catalyst Systems: Efficient Synthesis Of Conjugated Polymers Containing Vinyl Groups In Main Or Side Chain, Glen Brizius, Neil Pschirer, Winfried Steffen, Katherine Stitzer, Hans Conrad Zur Loye, Uwe Bunz

Hans Conrad zur Loye

The synthesis of novel conjugated polymers by acyclic diyne metathesis (ADIMET) is reported. These polymers are hybrids between poly(p-phenylenevinylene) and poly(p-phenyleneneethynylene) (PPE). They contain phenylene, ethynylene, and vinylene groups (PhPh, PPVE). Simple in situ catalysts formed from Mo(CO)6 and 4-chlorophenol were used to metathesize the dipropynyl(tetraalkyl)stilbene monomers. The monomers are made by a combination of Horner reactions and Heck-type couplings. The PPVEs form in high yields and are structurally defined. They show degrees of polymerization (Pn) of 30−220 repeating units (i.e. 60−450 benzene rings), demonstrating that the presence of the double bonds does not interfere with alkyne metathesis. The PPVEs …