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Synthesis and Crystal Structure of a Phenazine N-oxide

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Abstract

The preparation and crystal structure of 8-chloro-1H-pyrrolo[2,3-b]phenazine5-oxide (1) are described. Compound 1 formed dark purple crystals from deeply colored solution in methanol. Crystal plates were in the triclinic system, P-1 space group with unit cell parameters a = 6.9514(8), b = 9.1568(10), c = 10.2067(11), α = 84.509(2), β = 82.936(2), γ = 72.357(2) and a cell volume of 613.25(12) A−3. The title compound which contains the first example of the extensively conjugated pyrrolo-phenazine N-oxide system exhibits strong light absorption in the green to cyan wavelength range which disappears upon protonation.

Graphical Abstract

The synthesis, optical properties and crystal structure of the title compound is described.

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Acknowledgments

This work was supported in part by the National Institutes of Health, Grant Nos. AI72012 and CA132753. Support of the NMR facility by the National Science Foundation is acknowledged (CRIF Grant CHE-0741968).

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Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA, 92093, USA

    Kejia Ding, Sergey M. Dibrov & Thomas Hermann

Authors
  1. Kejia Ding
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  2. Sergey M. Dibrov
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  3. Thomas Hermann
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Correspondence to Thomas Hermann.

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Ding, K., Dibrov, S.M. & Hermann, T. Synthesis and Crystal Structure of a Phenazine N-oxide. J Chem Crystallogr 43, 550–553 (2013). https://doi.org/10.1007/s10870-013-0456-4

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  • DOI: https://doi.org/10.1007/s10870-013-0456-4

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