Dataset Information

Bright, Red Single-Molecule Emitters: Synthesis and Properties of Environmentally Sensitive Dicyanomethylenedihydrofuran (DCDHF) Fluorophores with Bisaromatic Conjugation.

ABSTRACT: A group of new fluorescent dye materials for single-molecule imaging applications comprised of an amine donor, a ?-system comprised of phenyl and thiophene rings and a 2-dicyanomethylene-3-cyano-2,5-dihydrofuran acceptor group have been synthesized. Relative to comparable single-ring compounds these doubly aromatic conjugated fluorophores have red-shifted absorption and emission usually accompanied by significantly increased quantum yields. Solvatochromism studies indicate that the photophysical properties of these dyes are sensitive to the solvent polarity and environmental rigidity. Photophysical studies demonstrate that these DCDHF dye materials are strong single-molecule emitters and the total number of detected photons per molecule is among the highest thus far for this family of fluorophores.

SUBMITTER: Lu Z

PROVIDER: S-EPMC2731435 | biostudies-literature | 2009 Feb

REPOSITORIES: biostudies-literature

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Publications

Bright, Red Single-Molecule Emitters: Synthesis and Properties of Environmentally Sensitive Dicyanomethylenedihydrofuran (DCDHF) Fluorophores with Bisaromatic Conjugation.

Lu Zhikuan Z Liu Na N Lord Samuel J SJ Bunge Scott D SD Moerner W E WE Twieg Robert J RJ

Chemistry of materials : a publication of the American Chemical Society 20090201 5

A group of new fluorescent dye materials for single-molecule imaging applications comprised of an amine donor, a π-system comprised of phenyl and thiophene rings and a 2-dicyanomethylene-3-cyano-2,5-dihydrofuran acceptor group have been synthesized. Relative to comparable single-ring compounds these doubly aromatic conjugated fluorophores have red-shifted absorption and emission usually accompanied by significantly increased quantum yields. Solvatochromism studies indicate that the photophysical ...[more]

PMID: 20140061

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Project description:The fluorescence lifetimes of most red emitting organic probes are under 4 nanoseconds, which is a limiting factor in studying interactions and conformational dynamics of macromolecules. In addition, the nanosecond background autofluorescence is a significant interference during fluorescence measurements in cellular environment. Therefore, red fluorophores with longer lifetimes will be immensely helpful. Azaoxa-triangulenium fluorophores ADOTA and DAOTA are red emitting small organic molecules with high quantum yield, long fluorescence lifetime and high limiting anisotropy. In aqueous environment, ADOTA and DAOTA absorption and emission maxima are respectively 540 nm and 556 nm, and 556 nm and 589 nm. Their emission extends beyond 700 nm. Both probes have the limiting anisotropy between 0.36-0.38 at their absorption peak. In both protic and aprotic solvents, their lifetimes are around 20 ns, making them among the longest-lived red emitting organic fluorophores. Upon labeling of avidin, streptavidin and immunoglobulin their absorption and fluorescence are red-shifted. Unlike in free form, the protein-conjugated probes have heterogeneous fluorescence decays, with the presence of both significantly quenched and unquenched populations. Despite the presence of significant local motions due to a flexible trimethylene linker, we successfully measured both intermediate nanosecond intra-protein motions and slower rotational correlation times approaching 100 ns. Their long lifetimes are unaffected by the cell membrane (hexadecyl-ADOTA) and the intra-cellular (DAOTA-Arginine) localization. Their long lifetimes also enabled successful time-gating of the cellular autofluorescence resulting in background-free fluorescence lifetime based images. ADOTA and DAOTA retain a long fluorescence lifetime when free, as protein conjugate, in membranes and inside the cell. Our successful measurements of intermediate nanosecond internal motions and long correlations times of large proteins suggest that these probes will be highly useful to study slower intra-molecular motions and interactions among macromolecules. The fluorescence lifetime facilitated gating of cellular nanosecond autofluorescence should be of considerable help in in vitro and in vivo applications.

Dataset Information

Bright, Red Single-Molecule Emitters: Synthesis and Properties of Environmentally Sensitive Dicyanomethylenedihydrofuran (DCDHF) Fluorophores with Bisaromatic Conjugation.

Publications

Bright, Red Single-Molecule Emitters: Synthesis and Properties of Environmentally Sensitive Dicyanomethylenedihydrofuran (DCDHF) Fluorophores with Bisaromatic Conjugation.

Similar Datasets

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