Macromolecular Rapid Communications, Vol.35, No.5, 566-573, 2014
Facile Synthesis of beta-Diketone Alcohols for Combined Functionality: Initiation, Catalysis, and Luminescence
Primary alcohol-functionalized -diketones (bdks) are successfully synthesized via facile one-step Claisen condensation between aromatic monoketones and epsilon-caprolactone (epsilon-CL). To demonstrate application potentials, these bdk alcohols are used to chelate with various Lewis acids, including Tb (III), Eu (III), and B (III). It is discovered that the resulting Tb (III) and Eu (III) diketonate complexes can serve as both catalysts and initiators for ring-opening polymerization (ROP) under solvent-free conditions, using lactide monomer as an example. The polylactides (PLAs) thus obtained exhibit luminescence properties characteristic of Tb (III) and Eu (III), respectively. On the other hand, boron-chelated diketone can initiate ROP of lactide in the presence of Sn(oct)(2), and affords a PLA material with dual-emission, i.e., fluorescence and room temperature phosphorescence. The synthesis described here represents a shortcut for the preparation of bdk-based macroligands and subsequent functional materials. image