Thienyl Difluoroboron β-Diketonates in Solution and Polylactide Media.

Abstract

Difluoroboron β-diketonates have impressive optical properties in both solution and the solid state. In particular, both fluorescence and room-temperature phosphorescence are present when the dyes are confined to a rigid matrix, such as poly(lactic acid) (PLA). To expand current knowledge and color range capabilities of this unique type of multi-emitting chromophore, a series of thienyl-substituted BF2bdk complexes have been synthesized. The photophysical properties were investigated in methylene chloride solution and in the solid state as dye/PLA blends. By varying donor ability, i.e. methyl, phenyl, methoxyl, and thienyl substituents, and by changing the dye loading in the PLA media (0.1-10% dye loading) red-shifted emission was achieved, important for biological imaging applications. In dilute CH2Cl2 solution, complexes exhibited absorptions ranging from 350 - 420 nm, solid-state fluorescence in PLA ranging from 390 - 500 nm, and oxygen sensitive phosphorescence ranging from 540 - 585 nm in PLA blends. Promising candidates as dye/PLA blends serve as models for dyepolymer conjugates for application as biological oxygen nanoprobes.