Dimerization of a reactive azaacene diradical: synthesis of a covalent azaacene cage
Two series of regioisomeric dicyanomethylene substituted dithienodiazatetracenes with formal para- or ortho-quinodimethane subunits were synthesized and characterized. Whereas the para-isomers (p-n, diradical index y0=0.01) are stable and isolable, the ortho-isomer (y0=0.98) dimerizes into a covalen...
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| Main Authors: | , , , , , , , , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
August 7, 2023
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| In: |
Angewandte Chemie. International edition
Year: 2023, Volume: 62, Issue: 32, Pages: 1-9 |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.202305712 |
| Online Access: | Resolving-System, kostenfrei, Volltext: https://doi.org/10.1002/anie.202305712 Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.202305712 
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| Author Notes: | Kathleen Fuchs, Samara Medina Rivero, Anna Weidlich, Frank Rominger, Noel Israel, Alexey A. Popov, Andreas Dreuw, Jan Freudenberg, Juan Casado, and Uwe H.F. Bunz |
| Summary: | Two series of regioisomeric dicyanomethylene substituted dithienodiazatetracenes with formal para- or ortho-quinodimethane subunits were synthesized and characterized. Whereas the para-isomers (p-n, diradical index y0=0.01) are stable and isolable, the ortho-isomer (y0=0.98) dimerizes into a covalent azaacene cage. Four elongated σ-CC bonds are formed and the former triisopropylsilyl(TIPS) -ethynylene groups transformed into cumulene units. The azaacene cage dimer (o-1)2 was characterized by X-ray single crystal structure analysis and temperature-dependent infrared (IR), electron paramagnetic resonance (EPR, solid-state), nuclear magnetic resonance (NMR) and ultraviolet-visible (UV/Vis) spectroscopies (solution) indicating reformation of o-1. |
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| Item Description: | Gesehen am 10.07.2023 |
| Physical Description: | Online Resource |
| ISSN: | 1521-3773 |
| DOI: | 10.1002/anie.202305712 |