Synthesis and characterization of N,N-Bis(2-hydroxyethyl) cinnamamide as a photo-responsive monomer

Abstract

N,N-Bis(2-hydroxyethyl) cinnamamide (BHECA), a diol monomer with a pendant photo-responsive cinnamamide group, was successfully synthesized in high yield from methyl cinnamate (MC) and diethanolamine (DEA) under mild conditions. This ammonolysis approach is characterized by readily available and safe raw material, high yield and easy separation. Also, it does not require the use of an organic solvent. The product was characterized with element analysis, FT-IR, 1H-NMR, MS, DSC and TGA. Its photo-response was tested by ultraviolet absorption. BHECA is able to undergo reversible [2+2] cycloaddition under alternating >260 nm and <260 nm ultraviolet irradiation and, therefore, appears to be a potential functional monomer for synthesis of novel photo-responsive polymers. © 2011 Koninklijke Brill NV, Leiden.