Synthesis of polymer organogelators using hydrogen bonding as physical cross-links

The synthesis of a monomer containing fourfold hydrogen bonding groups 2-(((6-(6-methyl-4[1H]pyrimidionylureido)hexyl)carbamoyl)oxy)ethyl methacrylate (UPyEMA) and its copolymerization with either n-butyl acrylate, tert-butyl acrylate, or styrene using reversible addition-fragmentation chain transfer (RAFT) polymerization is reported. The copolymers possessed high molecular weight and narrow molecular weight distributions and formed stable organogels in both chloroform and 1,2-dichlorobezene. Critical gelation concentrations were determined and the rheology of the organogels characterized. A novel monomer containing pyrene was prepared, and its polymerization under RAFT control was demonstrated. The pyrene-containing monomer was copolymerized with the polymer organogelators forming fluorescent organogels. It is proposed that these gels are suitable for two-photon upconversion applications.