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Expeditious, mechanochemical synthesis of BODIPY dyes.

ABSTRACT: BODIPY dyes have been synthesized under solvent-free or essentially solvent-free conditions, within about 5 minutes in an open-to-air setup by using a pestle and mortar, with yields that are comparable to those obtained via traditional routes that typically require reaction times of several hours to days.

SUBMITTER: Jameson LP

PROVIDER: S-EPMC3678757 | biostudies-other | 2013

REPOSITORIES: biostudies-other

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Expeditious, mechanochemical synthesis of BODIPY dyes.

Jameson Laramie P LP Dzyuba Sergei V SV

Beilstein journal of organic chemistry 20130423

BODIPY dyes have been synthesized under solvent-free or essentially solvent-free conditions, within about 5 minutes in an open-to-air setup by using a pestle and mortar, with yields that are comparable to those obtained via traditional routes that typically require reaction times of several hours to days. ...[more]

PMID: 23766791

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Synthesis of Water-Soluble Far-Red-Emitting Amphiphilic BODIPY Dyes.

Project description:We report the synthesis of two water-soluble BODIPY dyes with far-red absorption and near-infrared fluorescence following cell membrane insertion. Introduction of dicationic or dianionic groups imparts water solubility and prevents translocation of the dye through the plasma membrane for highly effective labeling. The dicationic form is particularly well localized to the plasma membrane and resists quenching even after >8 min of continuous light exposure. The dyes are almost completely nonemissive in water and other highly polar solvents, but display high-fluorescence yields in chloroform and upon insertion into the extracellular leaflet.

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Synthesis and Characterization of Hydrazine-Appended BODIPY Dyes and the Related Aminomethyl Complexes.

Project description:The synthesis and characterization of three new organic hydrazines containing BODIPY dyes is described. The respective aminomethyl complexes were also synthesized to aid in the assignment of the physical properties that were hydrazine-based vs. BODIPY-based. Incorporation of a BODIPY dye into an organic hydrazine introduced a reduction event (average value of -1.70 V vs. Cp2Fe/Cp2Fe+). Although two irreversible oxidation events were observed, it was unclear whether the oxidation events arose from BODIPY-based or amine/hydrazine-based oxidations. The respective BODIPY-appended hydrazine complexes exhibited excited state lifetimes on the order of 2-6 ns, suggesting the presence of a singlet excited state. The excited state lifetimes of the BODIPY-appended hydrazine complexes were about a factor of ten greater than the respective aminomethyl complexes. Computational analysis showed that by appending a BODIPY dye to a hydrazine fragment the hydrazine fragment becomes more susceptible to transfer H2 equivalents as protons and hydrides as opposed to H-atoms, which occurs with common organic hydrazines. Computational analysis also revealed that the BODIPY-based redox events can be used to manipulate the mechanism for H2 transfer from the BODIPY-appended hydrazine, where a BODIPY-based reduction favors H-atom transfer and a BODIPY-based oxidation favors proton transfer followed by hydride transfer.

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Aza-BODIPY dyes with enhanced hydrophilicity.

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Functionalization of 3,5,8-trichlorinated BODIPY dyes.

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Photochemical Properties and Stability of BODIPY Dyes.

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