Dimerization of a Reactive Azaacene Diradical: Synthesis of a Covalent Azaacene Cage [Data]

DOI

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.

Identifier
DOI https://doi.org/10.11588/data/QO118B
Related Identifier https://doi.org/10.1002/anie.202305712
Metadata Access https://heidata.uni-heidelberg.de/oai?verb=GetRecord&metadataPrefix=oai_datacite&identifier=doi:10.11588/data/QO118B
Provenance
Creator 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
Publisher heiDATA
Contributor Bunz, Uwe
Publication Year 2023
Funding Reference 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
Rights CC BY 4.0; info:eu-repo/semantics/openAccess; http://creativecommons.org/licenses/by/4.0
OpenAccess true
Contact Bunz, Uwe (Institute of Organic Chemistry, Heidelberg University)
Representation
Resource Type Dataset
Format application/zip
Size 570191; 254739; 336262; 32410964; 330366784; 70054
Version 1.0
Discipline Chemistry; Natural Sciences