Eugenol Biobased Polydiacetylene

Abstract

Eugenol, a natural compound with numerous biological activities, can be extracted from plants or obtained by depolymerizing lignin. It is also a prime building block for the design of biobased resins and polymers. As the transition from conventional to eco-friendly electronics is underway, new green synthetic approaches are being developed to obtain π-conjugated polymers. Therefore, the potential for using eugenol in this context caught our attention. Herein, we report the synthesis and single-crystal structural determination of a eugenol-based diacetylene (Eug-DA) monomer grafted with a carbamate moiety to achieve the stacking required for polymerization. The characteristic blue-violet color of polydiacetylenes (PDA) appears when DA monomer single crystals are left in ambient light or subjected to X-ray or UV irradiation. Similar blue-purple PDA crystals were also obtained by leaving a DA sample for 1 month at room temperature away from light. The characteristic peaks of PDA in Raman spectroscopy were observed, as were the usual thermochromism and solvatochromism properties of PDA.