Are N,N-dihydrodiazatetracene derivatives antiaromatic?

Shaobin Miao, Scott M. Brombosz, Paul V.R. Schleyer, Judy I. Wu, Stephen Barlow, Seth R. Marder, Kenneth I. Hardcastle, Uwe H.F. Bunz

Research output: Contribution to journalArticle

126 Scopus citations

Abstract

The synthesis and X-ray characterization of two new dialkynylated diazatetracenes and the corresponding N,N-dihydrodiazatetracenes are reported. The dialkynylated heteroacenes are packed in a brick-wall motif that enforces significant overlap of their π-faces. Cyclic voltammetry indicates that the dehydrogenated forms are easily reduced to their radical anions in solution. The planarity of these species validates the discussion of their aromaticity. Nucleus Independent Chemical Shift (NICS) computations demonstrate that both of these 20 π and 24 π electron systems are aromatic. Both experimental and computational results suggest that the aromaticity of the dihydroheteroacenes is reduced.

Original languageEnglish (US)
Pages (from-to)7339-7344
Number of pages6
JournalJournal of the American Chemical Society
Volume130
Issue number23
DOIs
StatePublished - Jun 11 2008
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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    Miao, S., Brombosz, S. M., Schleyer, P. V. R., Wu, J. I., Barlow, S., Marder, S. R., Hardcastle, K. I., & Bunz, U. H. F. (2008). Are N,N-dihydrodiazatetracene derivatives antiaromatic? Journal of the American Chemical Society, 130(23), 7339-7344. https://doi.org/10.1021/ja077614p