Cited by 144Luminescence and Fluorescent MaterialsMolecular Sensors and Ion DetectionPorphyrin and Phthalocyanine Chemistry

Pyrrolopyrrole Cyanine Dyes: A New Class of Near‐Infrared Dyes and Fluorophores

Fischer, Georg M., Isomäki‐Krondahl, Magnus, Göttker‐Schnetmann, Inigo, Daltrozzo, Ewald, Zumbusch, Andreas·2009·Chemistry – A European Journal

Abstract

NIRer there: Pyrrolopyrrole cyanine (PPCys) dyes, a new class of near‐infrared (NIR) fluorophores, are obtained by condensation of heteroarylacetonitrile and diketopyrrolopyrrole compounds (see picture). Complexation with BF 2 or BPh 2 yields strongly fluorescent, photostable NIR dyes that show high absorption cross‐sections and fluorescence quantum yields. Furthermore, alteration of the heterocycle can tune the main absorption between λ = 684 and 864 nm.magnified image Pyrrolopyrrole cyanine (PPCy) dyes are presented as a novel class of near‐infrared (NIR) chromophores, which are synthesized in a condensation reaction of diketopyrrolopyrrole with heteroarylacetonitrile compounds. Their optical properties are marked by strong and narrow‐band NIR absorptions. Complexation products with BF 2 and BPh 2 show strong NIR fluorescence and hardly any absorption in the visible range. We synthesized a series of new PPCys that differ only in the heterocyclic peripheral groups of the chromophore. With this strategy, the absorption spectra can be tuned between 684 and 864 nm, while high fluorescence quantum yields are maintained. The influence of the heterocycle on the optical properties of the dyes is discussed.

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Crossref · 10.1002/chem.200801996

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Authors
Fischer, G. M., Isomäki‐Krondahl, M., Göttker‐Schnetmann, I., Daltrozzo, E., & Zumbusch, A.
Affiliations
University of Konstanz (DE)
Venue
Chemistry – A European Journal
Publisher
Wiley
Published
2009-04-28
Volume
15
Issue
19
Pages
4857-4864
ISSN
  • 0947-6539 (ISSN-L)
  • 1521-3765
OpenAlex
W2114560209
Cited by
144
References
27
Citations by year
2026: 2 · 2025: 5 · 2024: 4 · 2023: 6 · 2022: 8 · 2021: 10 · 2020: 11 · 2019: 9 · 2018: 11 · 2017: 7 · 2016: 8 · 2015: 9 · 2014: 18 · 2013: 5 · 2012: 9
FWCI
4.99
Type
journal article
Language
en
Open access
closed
Locations
  • Chemistry - A European Journal (publishedVersion)
  • PubMed (publishedVersion)
Topics
  • Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
  • Physical Sciences › Chemistry › Spectroscopy › Molecular Sensors and Ion Detection
  • Physical Sciences › Materials Science › Materials Chemistry › Porphyrin and Phthalocyanine Chemistry
Keywords
near-infrared dyes, fluorophores, diketopyrrolopyrrole, fluorescence quantum yield, absorption cross section, absorption tuning, photostability
MeSH terms
Acetonitriles, Boron Compounds, Carbocyanines, Coloring Agents, Pyrroles, Solvents, Spectrometry, Fluorescence, Temperature, X-Ray Diffraction, Molecular Structure, Spectroscopy, Near-Infrared

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