4 years ago

Meta-Alkoxy-Substituted Difluoroboron Dibenzoylmethane Complexes as Environment-Sensitive Materials

Meta-Alkoxy-Substituted Difluoroboron Dibenzoylmethane Complexes as Environment-Sensitive Materials
Christopher A. DeRosa, Caroline Kerr, Cassandra L. Fraser, Margaret L. Daly
The optical properties of meta-alkoxy-substituted difluoroboron dibenzoylmethane dyes were investigated in solution and in the solid state. Meta-alkoxy substitution induced strong intramolecular charge transfer (ICT) from the oxygen-donating substituent to the halide and boron acceptors in the excited state, as compared to the π–π* transition that is observed with para-alkoxy substitution. The optical properties of para- and meta-substituted alkoxy boron dyes were evaluated by calculations, in dilute solution, and in solid-state films. When embedded in amorphous matrixes (e.g., PLA, PMMA, PS, cholesterol), all dyes showed fluorescence (F) and phosphorescence (P) emission. In this report, we show that meta-substitution resulted in enhanced solvatochromism and an increased phosphorescence-to-fluorescence ratio in solid-state films compared to analogous para-substituted samples. With enhanced phosphorescence intensity via the heavy-atom effect, iodo-substituted dyes were further studied in PLA–PEG nanoparticles. Oxygen calibrations revealed stronger phosphorescence and a greater oxygen-sensing range for the meta- versus para-alkoxy-substituted dyes, features that are important for oxygen-sensing materials design.

Publisher URL: http://dx.doi.org/10.1021/acsami.7b06910

DOI: 10.1021/acsami.7b06910

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