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Luminescent Mono-, Di-, and Tri-radicals: Bridging Polychlorinated Triarylmethyl Radicals by Triarylamines and Triarylboranes

Please always quote using this URN: urn:nbn:de:bvb:20-opus-208162
  • Up to three polychlorinated pyridyldiphenylmethyl radicals bridged by a triphenylamine carrying electron withdrawing (CN), neutral (Me), or donating (OMe) groups were synthesized and analogous radicals bridged by tris(2,6‐dimethylphenyl)borane were prepared for comparison. All compounds were as stable as common closed‐shell organic compounds and showed significant fluorescence upon excitation. Electronic, magnetic, absorption, and emission properties were examined in detail, and experimental results were interpreted using DFT calculations.Up to three polychlorinated pyridyldiphenylmethyl radicals bridged by a triphenylamine carrying electron withdrawing (CN), neutral (Me), or donating (OMe) groups were synthesized and analogous radicals bridged by tris(2,6‐dimethylphenyl)borane were prepared for comparison. All compounds were as stable as common closed‐shell organic compounds and showed significant fluorescence upon excitation. Electronic, magnetic, absorption, and emission properties were examined in detail, and experimental results were interpreted using DFT calculations. Oxidation potentials, absorption and emission energies could be tuned depending on the electron density of the bridges. The triphenylamine bridges mediated intramolecular weak antiferromagnetic interactions between the radical spins, and the energy difference between the high spin and low spin states was determined by temperature dependent ESR spectroscopy and DFT calculations. The fluorescent properties of all radicals were examined in detail and revealed no difference for high and low spin states which facilitates application of these dyes in two‐photon absorption spectroscopy and OLED devices.show moreshow less

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Metadaten
Author: Yohei Hattori, Evripidis Michail, Alexander Schmiedel, Michael Moos, Marco Holzapfel, Ivo Krummenacher, Holger Braunschweig, Ulrich Müller, Jens Pflaum, Christoph Lambert
URN:urn:nbn:de:bvb:20-opus-208162
Document Type:Journal article
Faculties:Fakultät für Physik und Astronomie / Physikalisches Institut
Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie
Fakultät für Chemie und Pharmazie / Institut für Organische Chemie
Language:English
Parent Title (English):Chemistry - A European Journal
Year of Completion:2019
Volume:25
Issue:68
Pagenumber:15463-15471
Source:Chemistry - A European Journal (2019) 25(68):15463-15471. DOI: 10.1002/chem.201903007
DOI:https://doi.org/10.1002/chem.201903007
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Tag:NIR OLED; density functional calculations; fluorescence; radical; two-photon absorption
Release Date:2020/10/22
Licence (German):License LogoCC BY-NC: Creative-Commons-Lizenz: Namensnennung, Nicht kommerziell 4.0 International