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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| Hauptverfasser: | , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
September 11, 2013
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| In: |
Chemistry - a European journal
Year: 2013, Jahrgang: 19, Heft: 41, Pages: 13811-13822 |
| ISSN: | 1521-3765 |
| DOI: | https://doi.org/10.1002/chem.201301903 |
| Online-Zugang: | 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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| Verfasserangaben: | Sonja Geib, Susanne C. Martens, Michaela Märken, Arina Rybina, Hubert Wadepohl, and Lutz H. Gade |
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| 520 | |a 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. | ||
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| 650 | 4 | |a fluorescence | |
| 650 | 4 | |a photophysics | |
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