Aliphatic polyketones via cross-metathesis polymerization: Synthesis and post-polymerization modification

Polyolefins attract considerable attention due to their vast consumption and wide application. In this study, cross-metathesis polymerization (CMP) is demonstrated to be an efficient and feasible method for the synthesis of aliphatic polyketones. The synthetic route features good yield, mild condition and easy operation. The success of CMP relies on the high cross-metathesis tendency between α-olefin and vinyl ketone units of monomer 2. Optimization of polymerization condition was conducted to generate unsaturated polyketone P0 (Mn,GPC = 14 kDa), and the results of kinetic study verified high efficiency and structural integrity of this system. Furthermore, post-polymerization modification of P0 by using thiol-Michael chemistry furnished functional polyketones P1–P6, and full conversion of the internal vinyl ketone groups of P0 was observed in each case. The pristine and functional polyketones P0–P6 were virtually soluble in most common organic solvents. In particular, hydrophobic and fluorescent polyketones (P5 and P6) were also obtained by this means. Therefore, this synthetic strategy shows promising future and exemplifies huge potential for the synthesis of a diverse range of functional polyketones.