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 language | English (US) |
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Pages (from-to) | 7339-7344 |
Number of pages | 6 |
Journal | Journal of the American Chemical Society |
Volume | 130 |
Issue number | 23 |
DOIs | |
State | Published - Jun 11 2008 |
Externally published | Yes |
ASJC Scopus subject areas
- Catalysis
- General Chemistry
- Biochemistry
- Colloid and Surface Chemistry