Azaacenes bearing five-membered rings
We report the synthesis of processible (dihydro)pyracyclene- and acenaphthylene-substituted azaacenes using condensation reactions in solution. The targets are characterized via cyclic voltammetry, X-ray crystallography, UV/Vis, fluorescence spectroscopy and DFT/NICS calculations. Formal hydrogenati...
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| Main Authors: | , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
August10, 2018
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| In: |
Chemistry - a European journal
Year: 2018, Volume: 24, Issue: 51, Pages: 13667-13675 |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201802900 |
| Online Access: | Verlag, Volltext: https://doi.org/10.1002/chem.201802900 Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201802900 
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| Author Notes: | Michael Ganschow, Silke Koser, Manuel Hodecker, Frank Rominger, Jan Freudenberg, Andreas Dreuw, and Uwe H.F. Bunz |
| Summary: | We report the synthesis of processible (dihydro)pyracyclene- and acenaphthylene-substituted azaacenes using condensation reactions in solution. The targets are characterized via cyclic voltammetry, X-ray crystallography, UV/Vis, fluorescence spectroscopy and DFT/NICS calculations. Formal hydrogenation of the annulated five-membered ring surprisingly alters emission in the solid-state as a consequence of modulation of aromaticity and HOMO-LUMO overlap. Five highly fluorescent, crystalline azaacenes were investigated as emitters in organic light-emitting diodes, and their performance with respect to luminance and efficiency was compared to that of structurally related azaacenes. |
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| Item Description: | Gesehen am 24.09.2019 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3765 |
| DOI: | 10.1002/chem.201802900 |