Published August 25, 2021
| Published + Supplemental Material
Journal Article
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Cata-Annulated Azaacene Bisimides
Abstract
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.
Additional Information
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. Issue Online: 26 August 2021; Version of Record online: 29 July 2021; Accepted manuscript online: 01 July 2021; Manuscript received: 03 May 2021. Crystallographic data: Deposition Number(s) 2080832 (2 a) and 2080833 (3-H2) contain(s) the supplementary crystallographic data for this paper. We thank the SFB 1249 for generous support. L.A. thanks the "Studienstiftung des Deutschen Volkes" for a scholarship. S.M.L. and D.C. were supported by the National Science Foundation under Grant No. (NSF 1954975) and the Donors of the American Chemical Society Petroleum Research Fund (57163-UNI1). Open access funding enabled and organized by Projekt DEAL. The authors declare no conflict of interest.Attached Files
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Supplemental Material - chem202101573-sup-0001-misc_information.pdf
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Additional details
- Eprint ID
- 109804
- Resolver ID
- CaltechAUTHORS:20210714-143935679
- SFB 1249
- Deutsche Forschungsgemeinschaft (DFG)
- Studienstiftung des Deutschen Volkes
- CHE-1954975
- NSF
- 57163-UNI1
- American Chemical Society Petroleum Research Fund
- Projekt DEAL
- Created
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2021-07-14Created from EPrint's datestamp field
- Updated
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2022-11-11Created from EPrint's last_modified field