The innovation engine for new materials

Michael Martinez

Michael Martinez




California Polytechnic State University, San Luis Obispo


Zachariah Page

Faculty Sponsor(s): 

Craig Hawker

Faculty Sponsor's Department(s): 

Chemistry and Biochemistry

Project Title: 

Incorporation of Donor-Acceptor Stenhouse Adducts onto Polymer Chains

Project Description: 

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.