Are N,N-Dihydrodiazatetracene Derivatives Antiaromatic?

Are N,N-Dihydrodiazatetracene Derivatives Antiaromatic?

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 d...

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Veröffentlicht in:Journal of the American Chemical Society 2008-06, Vol.130 (23), p.7339-7344
Hauptverfasser: Miao, Shaobin, Brombosz, Scott M, Schleyer, Paul v. R, Wu, Judy I, Barlow, Stephen, Marder, Seth R, Hardcastle, Kenneth I, Bunz, Uwe H. F
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container_end_page 7344
container_issue 23
container_start_page 7339
container_title Journal of the American Chemical Society
container_volume 130
creator Miao, Shaobin
Brombosz, Scott M
Schleyer, Paul v. R
Wu, Judy I
Barlow, Stephen
Marder, Seth R
Hardcastle, Kenneth I
Bunz, Uwe H. F
description 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.
doi_str_mv 10.1021/ja077614p
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title Are N,N-Dihydrodiazatetracene Derivatives Antiaromatic?
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