Functionalization of amphiphilic coil-rod-coil triblock copolymer poly(2-vinylpyridine)- b-poly( n-hexyl isocyanate)- b-poly(2-vinylpyridine) with florescence moiety and C 60

Abstract

We recently achieved quantitative synthesis of an amphiphilic coil-rod-coil triblock copolymer, poly(2-vinylpyridine)- b-poly( n-hexyl isocyanate)- b-poly(2-vinylpyridine), by coupling in situ living diblock copolymer poly(2-vinylpyridine)- b-poly( n-hexyl isocyanate) (P2VP- b-PHIC) using malonyl chloride in the presence of pyridine. This led to the introduction of an active methylene group that is a site for further functionalization in the rod block. The Michael addition reaction of the triblock copolymer with 7-(4-trifluoromethyl) coumarin acrylamide led to copolymer bearing a fluorescent pendent in the rod block. The fluorescent labeled copolymers were isolated in ∼94% yields. Similarly C 60 pendent was introduced to the rod block by the Bingel reaction. The yields of C 60 functionalized copolymers were ∼54%. The precursor and functionalized amphiphilic coil-rod-coil copolymer show diverse morphologies, such as micelles and vesicles by simply changing the solvent. For the C 60 functionalized block copolymer, structural constraints in micelles and vesicles prevented C 60 pendents to aggregate.