Thienyl Difluoroboron β-Diketonates in Solution and Polylactide Media*
Milena Kolpaczynska A B , Christopher A. DeRosa A B , William A. Morris A and Cassandra L. Fraser A C
+ Author Affiliations
- Author Affiliations
A Department of Chemistry, University of Virginia, McCormick Road, Charlottesville, VA 22904, USA.
B These authors contributed equally to this work.
C Corresponding author. Email: fraser@virginia.edu
Australian Journal of Chemistry 69(5) 537-545 https://doi.org/10.1071/CH15750
Submitted: 1 December 2015 Accepted: 18 January 2016 Published: 7 March 2016
Abstract
Difluoroboron β-diketonates (BF2bdks) 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 the current knowledge and colour 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 dichloromethane solution and in the solid state as dye/PLA blends. By varying donor ability, i.e. methyl, phenyl, methoxy, and thienyl substituents, and by changing the dye loading in the PLA media (0.1–10 % dye loading) red-shifted emission was achieved, which is important for biological imaging applications. In dilute CH2Cl2 solution, complexes exhibited absorptions ranging from 350 to 420 nm, solid-state fluorescence in PLA ranging from 390 to 500 nm, and oxygen sensitive phosphorescence ranging from 540 to 585 nm in PLA blends. Promising candidates as dye/PLA blends serve as models for dye–polymer conjugates for application as biological oxygen nanoprobes.
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