Synthesis and characterization of amphiphilic comb-polymers via ring-opening metathesis polymerization of exo,exo-5,6-bis(alkoxymethyl)-7-oxabicyclo[2.2.1]hept-2-enes

A number of exo,exo-5,6-bis(alkoxymethyl)-7-oxabicyclo[2.2.1]hept-2-enes (exo,exo-5,6-bis(alkoxymethyl)-7-oxanorbornenes) with long alkyl chains were prepared by reduction of the Diels-Alder adduct of furan and maleic anhydride, followed by alkylation with a series of different n-alkylbromides. These monomers were polymerized via ring-opening metathesis polymerization (ROMP) catalyzed by ruthenium trichloride in ethanolic solution. Contrary to a helical conformation as it was predicted by a previous molecular model study the poly(7-oxanorbornenes) adopt a coil conformation in solution. In bulk the materials show side chain crystallization.