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Cata-Annulated Azaacene Bisimides

Elter, Maximilian and Ahrens, Lukas and Luo, Stella M. and Rominger, Frank and Freudenberg, Jan and Cao, Dennis D. and Bunz, Uwe H. F. (2021) Cata-Annulated Azaacene Bisimides. Chemistry: a European Journal, 27 (48). pp. 12284-12288. ISSN 0947-6539. doi:10.1002/chem.202101573. https://resolver.caltech.edu/CaltechAUTHORS:20210714-143935679

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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.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/chem.202101573DOIArticle
ORCID:
AuthorORCID
Luo, Stella M./0000-0003-4003-7468
Freudenberg, Jan0000-0003-3398-8492
Cao, Dennis D.0000-0002-0315-1619
Bunz, Uwe H. F.0000-0002-9369-5387
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.
Funders:
Funding AgencyGrant Number
Deutsche Forschungsgemeinschaft (DFG)SFB 1249
Studienstiftung des Deutschen VolkesUNSPECIFIED
NSFCHE-1954975
American Chemical Society Petroleum Research Fund57163-UNI1
Projekt DEALUNSPECIFIED
Subject Keywords:azaacenes; butterfly dimer; bisimides; electron acceptors; heteroacenes
Issue or Number:48
DOI:10.1002/chem.202101573
Record Number:CaltechAUTHORS:20210714-143935679
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210714-143935679
Official Citation:Cata-Annulated Azaacene Bisimides. M. Elter, L. Ahrens, S. M. Luo, F. Rominger, J. Freudenberg, D. D. Cao, U. H. F. Bunz, Chem. Eur. J. 2021, 27, 12284; DOI: 10.1002/chem.202101573
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:109804
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:14 Jul 2021 18:28
Last Modified:01 Sep 2021 17:53

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