Cata-Annulated Azaacene Bisimides [data]


Ultra-electron-deficient azaacenes were synthesized via Buchwald-Hartwig coupling of ortho-diaminoarenes with chlorinated mellophanic diimide followed by oxidation of the intermediate N,N’-dihydro compounds with MnO2 or PbO2. The resulting cata-annulated bisimide azaacenes have ultrahigh electron affinities with first reduction potentials as low as −0.35 V recorded for a tetraazapentacene. Attempts to prepare a tetrakis(dicarboximide)tetraazaheptacene resulted in the formation of a symmetric butterfly dimer.

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Creator Elter, Maximilian ORCID logo; Ahrens, Lukas ORCID logo; Luo, Stella M. ORCID logo; Rominger, Frank; Freudenberg, Jan (ORCID: 0000-0003-0998-693X); Cao, Dennis D. ORCID logo; Bunz, Uwe H. F. ORCID logo
Publisher heiDATA
Contributor Elter, Maximilian
Publication Year 2024
Funding Reference Deutsche Forschungsgemeinschaft SFB 1249 ; Studienstiftung des Deutschen Volkes ; National Science Foundation NSF 1954975 ; American Chemical Society Petroleum Research Fund 57163-UNI1
Rights CC BY 4.0; info:eu-repo/semantics/openAccess;
OpenAccess true
Contact Elter, Maximilian (Heidelberg University, Institute of Organic Chemistry)
Resource Type Dataset
Format application/zip
Size 129912; 149578; 160; 9254068; 141107423; 421033; 19013689; 134124
Version 1.0
Discipline Chemistry; Natural Sciences