Isocyanoacetate-Aldehyde Polymerization: A Facile Tool toward Functional Oxazoline-Containing Polymers

As an important nitrogen source, isocyanides have been involved in numerous organic reactions. As a result, many complicated compounds have been successfully synthesized through isocyanide chemistry. However, compared with its popular research in organic reactions, the application of isocyanides in polymerization is less investigated. In this work, a new polymerization based on isocyanide monomers is established. By simply mixing diisocyanoacetates and dialdehydes in the presence of a catalytic system of CuCl/PPh₃ /organobase in dichloromethane at room temperature readily produces soluble and thermally stable oxazoline-containing polymers with moderate weight-averaged molecular weights (M_w up to 11 200) in excellent yields (up to 97%) after 6 h. Furthermore, introducing the tetraphenylethene moiety into the main chains endows the resultant polymers with aggregation-induced emission, which can function as fluorescent probes for Fe³⁺ ion detection with high sensitivity and selectivity. This work not only enriches the family of isocyanide-based polymerizations but also provides an efficient tool for the preparation of functional heterocycle-containing polymers.