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Part 1: Document Description
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Citation |
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Title: |
Dimerization of a Reactive Azaacene Diradical: Synthesis of a Covalent Azaacene Cage [Data] |
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Identification Number: |
doi:10.11588/data/QO118B |
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Distributor: |
heiDATA |
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Date of Distribution: |
2023-05-31 |
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Version: |
1 |
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Bibliographic Citation: |
Fuchs, Kathleen; Dr. Rivero, Samara M.; Weidlich, Anna; Dr. Rominger, Frank; Israel, Noel; Dr. Popov, Alexey A.; Prof. Dreuw, Andreas; Dr. Freudenberg, Jan; Prof. Casado, Juan; Prof. Bunz, Uwe, 2023, "Dimerization of a Reactive Azaacene Diradical: Synthesis of a Covalent Azaacene Cage [Data]", https://doi.org/10.11588/data/QO118B, heiDATA, V1 |
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Citation |
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Title: |
Dimerization of a Reactive Azaacene Diradical: Synthesis of a Covalent Azaacene Cage [Data] |
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Identification Number: |
doi:10.11588/data/QO118B |
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Authoring Entity: |
Fuchs, Kathleen (Institute of Organic Chemistry, Heidelberg University) |
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Dr. Rivero, Samara M. (Department of Physics&Astronomy, University of Sheffield) |
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Weidlich, Anna (Interdisciplinary Center for Scientific Computation, Heidelberg University) |
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Dr. Rominger, Frank (Institute of Organic Chemistry, Heidelberg University) |
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Israel, Noel (Center of Spectroelectrochemistry, Leibniz Institute for Solid State and Materials Research (IFW) Dresden) |
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Dr. Popov, Alexey A. (Center of Spectroelectrochemistry, Leibniz Institute for Solid State and Materials Research (IFW) Dresden) |
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Prof. Dreuw, Andreas (Interdisciplinary Center for Scientific Computation, Heidelberg University) |
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Dr. Freudenberg, Jan (Institute of Organic Chemistry, Heidelberg University) |
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Prof. Casado, Juan (Department of Physical Chemistry, University of Málaga) |
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Prof. Bunz, Uwe (Institute of Organic Chemistry, Heidelberg University) |
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Date of Production: |
2023-05-23 |
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Distributor: |
heiDATA |
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Access Authority: |
Bunz, Uwe |
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Holdings Information: |
https://doi.org/10.11588/data/QO118B |
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Study Scope |
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Keywords: |
Chemistry, diradical, dimerization, cumulene, azaacene cage, cyclization |
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Abstract: |
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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Methodology and Processing |
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Sources Statement |
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Data Access |
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Other Study Description Materials |
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Related Publications |
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Citation |
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Title: |
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; |
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Identification Number: |
10.1002/anie.202305712 |
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Bibliographic Citation: |
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; |
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Label: |
CV.zip |
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Notes: |
application/zip |
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DSC_TGA.zip |
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Notes: |
application/zip |
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IR.zip |
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Notes: |
application/zip |
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mass spectrometry.zip |
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Notes: |
application/zip |
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NMR.zip |
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Notes: |
application/zip |
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UV-VIS absorption.zip |
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Notes: |
application/zip |