Brilliant BODIPY−Fluorene Copolymers with Dispersed Absorption and Emission Maxima

Abstract

Four systems 1a – d were prepared to investigate the optical properties of copolymers comprised of polyfluorene doped with BODIPY-based fluors. The underlying hypothesis was energy harvested via the strong absorptivity of the major component, fluorine, would be primarily emitted from the BODIPY parts at much higher wavelengths. Optimization of the polymerization process as a function of the mol % of BODIPY, indicated that the brightest polymers were formed when approximately 4 fluorene units were co-polymerized with every BODIPY precursor. These polymers were cast into nanoparticles of ca 40 nm diameter. Treatment of clone 9 rat liver cells with suspensions of these particles resulted in uptake without encapsulation in lysosomes, or organelle targeting.

Recent Advances in the Synthesis and Applications of Organoborane Polymers

“…Adapted with permission from Cheng et al [51]. Copyright 2012 The Royal Society of Chemistry a result of efficient energy transfer from the oligofluorene bridging moieties to the BODIPY chromophores [130].…”

BODIPY Fluorophore Toolkit for Probing Chemical Reactivity and for Tagging Reactive Functional Groups

“…[14] These dyes are uniquely suited to probing chemical reactions because unlike other common high-quantum-yield fluorophore dyes, they do not have accessible lone pairs that could bind to transition metals nor protic functional groups that could interfere with a chemical reagent's native reactivity. [15][16][17] Consistent with these recent advances, the ability to gain insight into reactivity by fluorescence microscopy is a growing application area with less than 10 reported examples. [14] Essential to the goal of enabling these studies through synthesis is the development of strategies to attach these dyes through tethers, namely unreactive chains such as alkyl groups, to remote reactive groups, for example, alkynes, olefins, alcohols, esters, epoxides, phosphines, and transitionmetal complexes.…”

Highly water-soluble, near-infrared emissive BODIPY polymeric dye bearing RGD peptide residues for cancer imaging

“…[6, 10, 11] Very recently, we and other groups reported some deep-red and near-infrared emissive polymeric BODIPY dyes. [12–16] However, all these BODIPY polymeric dyes are insoluble in aqueous solution. [12–16]…”