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Donor–acceptor Stenhouse adducts (DASAs) are a new class of photoswitches that respond to visible light by
converting from a triene form to the corresponding cyclopentenone form, resulting in a simultaneous colored-tocolorless,
hydrophobic-to-hydrophilic, and extended-to-collapsed transition. This project aims to integrate DASAs
into polymeric systems to take advantage of these unique properties, generating new stimuli responsive materials
with applications in amine-detection. Here, we describe how an activated furan precursor to DASA can be
functionalized with a norbornene-handle useful for ring opening metathesis polymerization (ROMP) under facile
conditions. First, 2-aminoethanol was reacted with ethylisocyanate to yield 1-ethyl-3-(2-hydroxyethyl)urea,
followed by a Steglich esterification with exo-5-norbornenecarboxylic acid. The norbonene-urea adduct was reacted
with malonyl dichloride to form a functional barbituric acid derivative capable of undergoing a rapid Knoevenagel
condensation with furfural to provide the desired activated furan-norbornene monomer. ROMP of this novel
monomer is currently under investigation.