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Tuning redox chemistry and photophysics in core-substituted tetraazaperopyrenes (TAPPs)

Core substitution of tetraazaperopyrenes (TAPPs) has been achieved, and with it, considerable variation of their photo- and redox-chemical properties. Through Suzuki cross coupling starting from the fourfold core-brominated tetraazaperopyrene, aryl-substituted TAPPs were synthesized, which displayed...

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Bibliographic Details
Main Authors: Geib, Sonja (Author) , Martens-Kruck, Susanne (Author) , Märken, Michaela (Author) , Rybina, Arina (Author) , Wadepohl, Hubert (Author) , Gade, Lutz H. (Author)
Format: Article (Journal)
Language:English
Published: September 11, 2013
In: Chemistry - a European journal
Year: 2013, Volume: 19, Issue: 41, Pages: 13811-13822
ISSN:1521-3765
DOI:https://doi.org/10.1002/chem.201301903
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/https://doi.org/10.1002/chem.201301903
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/chem.201301903
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Author Notes:Sonja Geib, Susanne C. Martens, Michaela Märken, Arina Rybina, Hubert Wadepohl, and Lutz H. Gade
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Summary:Core substitution of tetraazaperopyrenes (TAPPs) has been achieved, and with it, considerable variation of their photo- and redox-chemical properties. Through Suzuki cross coupling starting from the fourfold core-brominated tetraazaperopyrene, aryl-substituted TAPPs were synthesized, which displayed very high fluorescence quantum yields (up to 100 %) in solution. Besides the Suzuki reactions, Stille and Sonogashira cross-couplings were also found to be suitable methods for core derivatization, as demonstrated in the syntheses of alkynyl-substituted tetraazaperopyrene congeners. Furthermore, TAPPs incorporating intramolecular donor-acceptor combinations of aromatic units (8, 9) were accessible by coupling the electron-poor peropyrene core with electron-rich aromatic units, which act as strong electron donors. Finally, C-heteroatom coupling (O, S, N) gave rise to novel TAPP derivatives with strongly modified redox-chemical behaviour and photophysics in the solid state as well in solution. In particular, TAPP derivatives displaying red fluorescence were obtained for the first time.
Item Description:Gesehen am 29.01.2020
Physical Description:Online Resource
ISSN:1521-3765
DOI:https://doi.org/10.1002/chem.201301903

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