Potential Building Blocks for 1,4-Dihydro-N-heteroacenes

M. John Plater* (Corresponding Author), William T. A. Harrison

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
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Abstract Studies have been performed aimed at the synthesis of N-heteroacenes via substitution reactions of 4,5-difluoro-1,2-dinitrobenzene with a diamine. The fluorine atoms are displaced first, followed by an activated nitro group. Two intermediates have been characterised by X-ray single-crystal structure determinations. Their intermolecular interactions were examined by Hirshfeld surfaces to assess their suitability for organic molecular electronics. The high reactivity of the phenazine, which is prone to oxidise and rearrange, as are displacement products prepared from it, is explained by the formation of a cis-aci-nitro form from the secondary amine of the phenazine and a nitro group.
Original languageEnglish
Article numbere202200092
Number of pages7
Issue number6
Early online date8 Jun 2022
Publication statusPublished - Jun 2022

Bibliographical note

Open Access via Wiley agreement

Data Availability Statement

The data that support the findings of this study are available in the supplementary material of this article.


  • 4,5-difluoro-1,2-dinitrobenzene
  • N-heteroacenes
  • iterative synthesis
  • N-methyl-o-phenylenediamine


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