Renewable isosorbide‐enchained semi‐fluorinated aromatic ether polymers

Abstract

AbstractIsosorbide‐based renewable semi‐fluorinated polymers were synthesized via base‐mediated step‐growth polycondensation of isosorbide diol monomer with bis‐trifluorovinyl ether (TFVE) monomer in excellent yields. As the first example employing secondary alcohols in this addition/elimination polymerization affording fluorinated arylene vinylene ether (FAVE) polymers, reasonable to high‐molecular weights (10–84 kDa) and reproducible glass transition temperatures (Tg) ranging from 120 to 130°C were achieved. Containing 23–31 wt.% renewable isosorbide repeat unit, the amorphous polymers are processable in common organic solvents and form tough, transparent films. Depending on basic conditions, these renewable semi‐fluorinated polymers contain reactive fluoroalkene enchainment for post‐polymerization functionalization and further retain the ability to thermally crosslink without the need for catalysts or initiators. Structural characterization of this complex asymmetric polymer was determined by multi‐nuclear NMR including multiple 2D‐NMR techniques. Renewable FAVE chemistry based on isosorbide presents an intriguing option for alternative renewable materials containing fluorine.