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Synthesis of donor-substituted meso-phenyl and meso-ethynylphenyl BODIPYs with broad absorption

DOI zum Zitieren der Version auf EPub Bayreuth: https://doi.org/10.15495/EPub_UBT_00004733
URN to cite this document: urn:nbn:de:bvb:703-epub-4733-2

Title data

Gräf, Katja ; Körzdörfer, Thomas ; Kümmel, Stephan ; Thelakkat, Mukundan:
Synthesis of donor-substituted meso-phenyl and meso-ethynylphenyl BODIPYs with broad absorption.
In: New Journal of Chemistry. Vol. 37 (2013) Issue 5 . - pp. 1417-1426.
ISSN 1144-0546
DOI der Verlagsversion: https://doi.org/10.1039/c3nj00157a

Project information

Project title:
Project's official titleProject's id
Fotophysik synthetischer und biologischer multichromophorer SystemeGRK 1640

Project financing: Deutsche Forschungsgemeinschaft

Abstract

We report the synthesis of meso-ethynylphenyl BODIPYs and compare their properties with the corresponding meso-phenyl derivatives. Both types of BODIPYs carry a 2-cyano-3-acrylic acid anchoring moiety and either methyl groups or 4,4′-dimethoxytriphenylamine (MeOTPA) donor groups at positions 3 and 5. All compounds were characterized by NMR, UV/vis and cyclic voltammetry. The MeOTPA-substituted BODIPYs show an excellent panchromatic absorption with high molar extinction coefficients over the whole UV/vis range up to the near-IR region. The most impressive absorption was exhibited by the MeOTPA-substituted meso-ethynylphenyl BODIPY which strongly absorbs up to 1030 nm. By cyclic voltammetry measurements, all compounds were identified to be electrochemically stable in solution. Further, it was observed that the value of the LUMO level can be tuned by the meso-substituent. The HOMO level is determined by the donor substituents (−5.41 ± 0.03 eV and −4.84 ± 0.01 eV for BODIPYs with methyl groups and MeOTPA donor groups, respectively). These findings were further supported by DFT calculations. To evaluate the potential of the BODIPYs as sensitizers, the incident photon-to-current conversion efficiencies of solid-state dye-sensitized solar cells were measured. The photoaction spectra clearly show that the BODIPYs contribute to the photocurrent generation over their entire absorption region.

Further data

Item Type: Article in a journal
Additional notes (visible to public): ISI:000317927600021
DDC Subjects: 500 Science > 540 Chemistry
Institutions of the University: Faculties
Faculties > Faculty of Mathematics, Physics und Computer Science > Department of Physics > Chair Theoretical Physics IV > Chair Theoretical Physics IV - Univ.-Prof. Dr. Stephan Kümmel
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Macromolecular Chemistry I
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Applied Functional Polymers > Professor Applied Functional Polymers - Univ.-Prof. Dr. Mukundan Thelakkat
Graduate Schools
Graduate Schools > Graduiertenkollegs der Deutschen Forschungsgemeinschaft (DFG)
Faculties > Faculty of Mathematics, Physics und Computer Science
Faculties > Faculty of Mathematics, Physics und Computer Science > Department of Physics
Faculties > Faculty of Mathematics, Physics und Computer Science > Department of Physics > Chair Theoretical Physics IV
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Professor Applied Functional Polymers
Language: English
Originates at UBT: Yes
URN: urn:nbn:de:bvb:703-epub-4733-2
Date Deposited: 26 Aug 2020 10:30
Last Modified: 26 Aug 2020 10:30
URI: https://epub.uni-bayreuth.de/id/eprint/4733

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