Persistent Identifier
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doi:10.11588/data/QO118B |
Publication Date
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2023-05-31 |
Title
| Dimerization of a Reactive Azaacene Diradical: Synthesis of a Covalent Azaacene Cage [Data] |
Author
| Fuchs, Kathleen (Institute of Organic Chemistry, Heidelberg University)
Dr. Rivero, Samara M. (Department of Physics&Astronomy, University of Sheffield)
Weidlich, Anna (Interdisciplinary Center for Scientific Computation, Heidelberg University)
Dr. Rominger, Frank (Institute of Organic Chemistry, Heidelberg University)
Israel, Noel (Center of Spectroelectrochemistry, Leibniz Institute for Solid State and Materials Research (IFW) Dresden)
Dr. Popov, Alexey A. (Center of Spectroelectrochemistry, Leibniz Institute for Solid State and Materials Research (IFW) Dresden)
Prof. Dreuw, Andreas (Interdisciplinary Center for Scientific Computation, Heidelberg University)
Dr. Freudenberg, Jan (Institute of Organic Chemistry, Heidelberg University)
Prof. Casado, Juan (Department of Physical Chemistry, University of Málaga)
Prof. Bunz, Uwe (Institute of Organic Chemistry, Heidelberg University) |
Point of Contact
|
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Bunz, Uwe (Institute of Organic Chemistry, Heidelberg University) |
Description
| 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. |
Subject
| Chemistry |
Keyword
| diradical
dimerization
cumulene
azaacene cage
cyclization |
Related Publication
| Fuchs K., Rivero S. M., Weidlich A., Rominger F., Israel N., Popov A. A., Dreuw A., Freudenberg J., Casado J., Bunz U. H. F. Dimerization of a Reactive Azaacene Diradical: Synthesis of a Covalent Azaacene Cage. Angew Chem Int Ed Engl. 2023 May 23; e202305712; doi: 10.1002/anie.202305712 https://doi.org/10.1002/anie.202305712 |
Language
| English |
Production Date
| 2023-05-23 |
Funding Information
| Deutsche Forschungsgemeinschaft (SFB) 1249 and grant PO 1602/11-1 to AAP
Spanish Ministry of Science, Innovation and Universities MCIU, project MINECO/FEDER and the Junta de Andalucía (PROYEXCEL-0328)
Research Central Services (SCAI) of the university of Málaga |