Water‐Soluble Perylene Dyes

Schmidt, Cordula D.; Hirsch, Andreas

doi:10.1002/9783527630554.ch13

Ideas in Chemistry and Molecular Sciences 2010

DOI: 10.1002/9783527630554.ch13

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Water‐Soluble Perylene Dyes

Cordula D. Schmidt

Andreas Hirsch

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Cited by 5 publications

(1 citation statement)

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“…Perylenediimide (PDI) dyes are intensely colored with high molar absorptivities and measurable fluorescence quantum yields and lifetimes and have been used as electron-transfer acceptors. , They are photostable, oxidatively and reductively stable, and stable in aqueous environments. − PDI derivatives have been incorporated into dyad and oligomeric assemblies with ultrafast transient absorption measurements used to investigate excited-state energy and electron transfer and the appearance of transient redox-separated states. − The oxidized forms of the dyes have redox potentials that are sufficient to drive water oxidation and excited-state redox potentials sufficient to undergo electron injection into the conduction band of TiO 2 . , …”

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confidence: 99%

Ultrafast, Light-Induced Electron Transfer in a Perylene Diimide Chromophore-Donor Assembly on TiO₂

Brennaman

Norris

Gish

et al. 2015

J. Phys. Chem. Lett.

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Surface-bound, perylenediimide (PDI)-based molecular assemblies have been synthesized on nanocrystalline TiO2 by reaction of a dianhydride with a surface-bound aniline and succinimide bonding. In a second step, the Fe(II) polypyridyl complex [Fe(II)(tpy-PhNH2)2](2+) was added to the outside of the film, also by succinimide bonding. Ultrafast transient absorption measurements in 0.1 M HClO4 reveal that electron injection into TiO2 by (1)PDI* does not occur, but rather leads to the ultrafast formation of the redox-separated pair PDI(•+),PDI(•-), which decays with complex kinetics (τ1 = 0.8 ps, τ2 = 15 ps, and τ3 = 1500 ps). With the added Fe(II) polypyridyl complex, rapid (<25 ps) oxidation of Fe(II) by the PDI(•+),PDI(•-) redox pair occurs to give Fe(III),PDI(•-) persisting for >400 μs in the film environment.

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mentioning

confidence: 99%

Ultrafast, Light-Induced Electron Transfer in a Perylene Diimide Chromophore-Donor Assembly on TiO₂

Brennaman

Norris

Gish

et al. 2015

J. Phys. Chem. Lett.

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Molekülverbände von Perylenbisimid‐Farbstoffen in Wasser

2012

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Perylenbisimide zählen zu den bedeutendsten funktionellen Farbstoffen mit vielfältigen Anwendungsmöglichkeiten. Aufgrund ihrer chemischen Robustheit, Photostabilität und herausragenden optischen und elektronischen Eigenschaften wurden sie als Pigmentfarbstoffe, Fluoreszenzsonden sowie n‐Halbleiter in der organischen Elektronik und Photovoltaik eingesetzt. Das ausgedehnte quadrupolare π‐System dieser Farbstoffklasse ermöglichte außerdem die Herstellung zahlreicher supramolekularer Architekturen mit faszinierenden photophysikalischen Eigenschaften. Jedoch blieb der supramolekulare Ansatz zur Bildung von Perylenbisimid‐Molekülverbänden größtenteils organischen Medien vorbehalten. Erfreulicherweise gab es in den letzten Jahren beachtliche Bemühungen zur Entwicklung von wasserlöslichen Perylenbisimiden und deren Anwendungen in wässrigen Medien. Dieser Aufsatz gibt einen aktuellen Überblick über die Selbstorganisation von Perylenbisimiden durch π‐π‐Wechselwirkung im wässrigen Medium. Synthetische Strategien zur Herstellung von wasserlöslichen Perylenbisimiden und der Einfluss des Wassers auf die π‐π‐Stapelung von Perylenbisimiden, sowie daraus resultierende Anwendungen werden eingehend diskutiert.

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Highly Fluorescent and Water‐Soluble Diketopyrrolopyrrole Dyes for Bioconjugation

et al. 2015

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The preparation of highly water-soluble and strongly fluorescent diketopyrrolopyrrole (DPP) dyes using an unusual taurine-like sulfonated linker has been achieved. Exchanging a phenyl for a thienyl substituent shifts the emission wavelength to near l = 600 nm. The free carboxylic acid group present in these new derivatives was readily activated and the dyes were subsequently covalently linked to a model protein (bovine serum albumin; BSA). The bioconjugates were characterized by electronic absorption, fluorescence spectroscopy and MALDI-TOF mass spectrometry, thus enabling precise determination of the labeling density (ratio DPP/BSA about 3 to 8). Outstanding values of fluorescence quantum yield (30 % to 59 %) for these bioconjugates are obtained. The photostability of these DPP dyes is considerably greater than that of fluorescein under the same irradiation conditions. Remarkably low detection limits between 80 and 300 molecules/mm 2 were found for the BSA bioconjugates by fluorescence imaging with a epifluorescence microscope.

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Water‐Soluble Perylene Dyes

Cited by 5 publications

References 93 publications

Ultrafast, Light-Induced Electron Transfer in a Perylene Diimide Chromophore-Donor Assembly on TiO₂

Ultrafast, Light-Induced Electron Transfer in a Perylene Diimide Chromophore-Donor Assembly on TiO₂

Molekülverbände von Perylenbisimid‐Farbstoffen in Wasser

Highly Fluorescent and Water‐Soluble Diketopyrrolopyrrole Dyes for Bioconjugation

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About

Water‐Soluble Perylene Dyes

Cited by 5 publications

References 93 publications

Ultrafast, Light-Induced Electron Transfer in a Perylene Diimide Chromophore-Donor Assembly on TiO2

Ultrafast, Light-Induced Electron Transfer in a Perylene Diimide Chromophore-Donor Assembly on TiO2

Molekülverbände von Perylenbisimid‐Farbstoffen in Wasser

Highly Fluorescent and Water‐Soluble Diketopyrrolopyrrole Dyes for Bioconjugation

Contact Info

Product

Resources

About

Ultrafast, Light-Induced Electron Transfer in a Perylene Diimide Chromophore-Donor Assembly on TiO₂

Ultrafast, Light-Induced Electron Transfer in a Perylene Diimide Chromophore-Donor Assembly on TiO₂