Novel thermally cross-linkable poly[(arylenedioxy)(diorganylsilylene)]s based on curcumin: Synthesis and characterization

Curcumin has attracted much attention due to its chemopreventive and anti-inflammatory properties. Here we describe the synthesis of poly[(arylenedioxy)(diorganylsilylene)]s via polycondensation between curcumin and various diorganodichlorosilanes. These novel polymers incorporate the β-diketone unit of curcumin as well as the Si-O bond in the backbone. The polymer structure was characterized by means of ¹HNMR, FTIR, and elemental analysis, while GPC results showed high molecular weights. Preliminary cell culture results suggest lack of cytotoxicity, which is important for potential applications such as implant and scaffold materials. The T _gs of these polymers are in the 24 to 131°C range, tunable by altering the pendant organic groups. The un-cross-linked polymers are stable at 250°C in air. The presence of vinyl groups in the backbone also allows the possibility for thermal cross-linking. DSC and rheology data demonstrate that the materials can cross-link at a temperature above 200°C which suggests the feasibility of melt processing these polymers via a technique wherein a low viscosity polymer is made to flow into a heated mold where it cross-links over time and becomes a rigid thermoset material.