Chemo-enzymatic synthesis of a levoglucosenone-derived bi-functional monomer and its ring-opening metathesis polymerization in the green solvent Cyrene™

The quite recent, yet quickly expanding, norbornene-levoglucosenone-based monomer family was extended to include a novel bi-functional methacrylate monomer that can be readily synthesized through a chemo-enzymatic pathway. The norbornene moiety was selectively polymerized via ring-opening metathesis polymerization (ROMP) under ambient conditions where Cyrene (TM) was explored for the first time as a green bio-alternative organic solvent for ROMP reactions. The activity of the metathesis catalysts was finely tuned in Cyrene (TM), versus common and toxic solvents such as dichloromethane, resulting in highly thermostable functional polymers with a T-d5% up to 401 degrees C and a T-g of -16.8 degrees C.