Abstract
1,4-Di(2-ethylhexyl)2,5-divinylbenzene, 1,4-di(2-ethylhexyloxy)-2,5-divinylbenzene, and 9,9-di(2-ethylhexyl)-2,7-divinylfluorene were synthesized from the respective dialdehydes and ADMET polymerized using Grubbs II or Grubbs−Hoveyda−Grela-type olefin metathesis catalysts. The continuous removal of ethene under a dynamic vacuum of 20 mbar at elevated temperatures in high boiling solvents (1,2-dichlorobenzene) resulted in the formation of long-chain poly[2,5-di(2-ethylhexyl)-p-phenylenevinylene] (Mn > 100 kDa, Pn = 330, Mw/Mn = 3.1) and poly[9,9-di(2-ethylhexyl)fluorenyl-2,7-vinylene] (Mn > 70 kDa, Pn = 178). The PPV forms a free-standing film after evaporation of a toluene solution. 1,3-(Diisopropenyl)ferrocene could not be polymerized in this manner; ferrocene-containing polymers were obtained with 1,1′-di(4-vinylphenyl)-3,3′,4,4′-tetramethylferrocene.
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