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

The DOI matches its Crossref record; 26 of the 27 references it cites were found in a registry or an index.

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
DOI 10.1002/chem.200801996
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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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Research works printed but not linked: 7

  1. Zollinger H., 2003, Color Chemistry
  2. W. Sulger PhD thesis University of Konstanz Germany 1981;
  3. T. Schlatterer PhD thesis University of Konstanz Germany 2001;
  4. D. Samson PhD thesis University of Konstanz Germany 2009;
  5. Abel E. W., 1956, J. Chem. Soc., 4697
  6. Crystal data for10 e: C64H70B2F4N6O2⋅2 CH2Cl2 M=1222.73 g mol−1 triclinic space groupP$\bar 1$(no. 2) a=11.4876(9) b=11.9739(9) c=12.2707(10) Å α=111.635(6) β=95.286(6) γ=95.925(6)° V=1545.0(2) Å3 Z=1 ρcalcd=1.314 g cm−3 μ(MoKα)=0.254 cm−1 T=100 K dichroic purple–green fragment STOE IPDS T2 reflections measured: 28 784 unique reflections: 8311 hklrange: −15.15 −16.16 −16.16 2θmax=58.42° F2refinement parameters: 385 R1=0.0785 for 4981 data (Fo>4s(Fo)) 0.1422 (all data) wR2=0.1242 for 4981 data (Fo>4s(Fo)) 0.1420 (all data) Rint=0.1471 GOF=1.037. CCDC‐703296 contains the supplementary crystallographic data for this structure; these data can be obtained free of charge from The Cambridge Crystallographic Data Centre viawww.ccdc.cam.ac.uk/data_request/cif
  7. T. Klumpp PhD thesis University of Konstanz Germany 1995.

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Metadata

Authors
Fischer, G. M., Isomäki‐Krondahl, M., Göttker‐Schnetmann, I., Daltrozzo, E., & Zumbusch, A.
Affiliations
University of Konstanz (DE)
ORCID
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
DOI
10.1002/chem.200801996
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
Licence
onlinelibrary.wiley.com/termsAndConditions#vor (vor)
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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