Oxygen sensing difluoroboron dinaphthoylmethane polylactide

Christopher A. DeRosa, Jelena Samonina-Kosicka, Ziyi Fan, Hansford C. Hendargo, Douglas H. Weitzel, Gregory M. Palmer, Cassandra L. Fraser

Research output: Contribution to journalArticlepeer-review

90 Scopus citations

Abstract

Dual emissive properties of solid-state difluoroboron β-diketonate-poly(lactic acid) (BF2bdk-PLA) materials have been utilized as biological oxygen sensors. Dyes with red-shifted absorption and emission are important for multiplexing and in vivo imaging, thus hydroxyl-functionalized dinaphthoylmethane initiators and dye-PLA conjugates BF2dnm(X)PLA (X = H, Br, I) with extended conjugation were synthesized. The luminescent materials show red-shifted absorbance (∼435 nm) and fluorescence tunability by molecular weight. Fluorescence colors range from yellow (∼530 nm) in 10-12 kDa polymers to green (∼490 nm) in 20-30 kDa polymers. Room-temperature phosphorescence (RTP) and thermally activated delayed fluorescence (TADF) are present under a nitrogen atmosphere. For the iodine-substituted derivative, BF2dnm(I)PLA, clearly distinguishable fluorescence (green) and phosphorescence (orange) peaks are present, making it ideal for ratiometric oxygen-sensing and imaging. Bromide and hydrogen analogues with weaker relative phosphorescence intensities and longer phosphorescence lifetimes can be used as highly sensitive, concentration independent, lifetime-based oxygen sensors or for gated emission detection. BF2dnm(I)PLA nanoparticles were taken up by T41 mouse mammary cells and successfully detected differences in oxygen levels during in vitro ratiometric imaging.

Original languageEnglish (US)
Pages (from-to)2967-2977
Number of pages11
JournalMacromolecules
Volume48
Issue number9
DOIs
StatePublished - May 12 2015

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