Abstract
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 language | English |
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Article number | e202200092 |
Number of pages | 7 |
Journal | ChemistryOpen |
Volume | 11 |
Issue number | 6 |
Early online date | 8 Jun 2022 |
DOIs | |
Publication status | Published - Jun 2022 |
Bibliographical note
Open Access via Wiley agreementData Availability Statement
The data that support the findings of this study are available in the supplementary material of this article.Keywords
- 4,5-difluoro-1,2-dinitrobenzene
- N-heteroacenes
- iterative synthesis
- N-methyl-o-phenylenediamine