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. 2022 Mar;11(3):e202100150.
doi: 10.1002/open.202100150. Epub 2021 Aug 25.

A Potential Iterative Approach to 1,4-Dihydro-N-Heteroacene Arrays

Affiliations

A Potential Iterative Approach to 1,4-Dihydro-N-Heteroacene Arrays

M John Plater et al. ChemistryOpen. 2022 Mar.

Abstract

A new method for the synthesis of substituted 1,4-dihydrophenazines is reported and the structure of N-butyl-5-methyl-3-nitro-5,10-dihydrophenazine is proven by an X-ray single-crystal structure determination.

Keywords: N-heteroacenes; heterocycles; iterative synthesis; nucleophilic substitution; phenazines.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
A comparison of pentacene with an N‐heteroacene.
Figure 2
Figure 2
The reaction of o‐phenylenediamines 35 was studied with 4,5‐difluoro‐1,2‐dinitrobenzene 6.
Figure 3
Figure 3
Phenazines 8–10.
Scheme 1
Scheme 1
Synthesis of compound 11 in low yield by nucleophilic displacement of a nitro group.
Figure 4
Figure 4
The molecular structure of compound 11 showing 50 % displacement ellipsoids.

References

    1. Bredas J. L., Calbert J. P., da Silva Filho D. A., Cornil J., Org. Semi. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5804–5809. - PMC - PubMed
    1. Cheng Y. C., Silbey R. J., da Silva Filho D. A., Calbert J. P., Cornil J., Bredas J. L., J. Chem. Phys. 2003, 118, 3764.
    1. Hummer K., Ambrosch-Draxl C., Phys. Rev. B: Condens. Matter Mater. Phys. 2005, 72, 205205.
    1. Nabok D., Puschnig P., Ambrosch-Draxl C., Werzer O., Resel R., Smilgies D.-M., Phys. Rev. B: Condens. Matter Mater. Phys. 2007, 76, 235322.
    1. Sharifzadeh S., Biller A., Kronik L., Neaton J. B., Phys. Rev. B: Condens. Matter Mater. Phys. 2012, 85, 125307.

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