期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 19, 期 12, 页码 3898-3904出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201203113
关键词
aromaticity; fluorescence; heterocycles; polycycles
资金
- Lundbeck Foundation
- Danish Research Council for Independent Research [09-066663]
We describe herein the first synthesis of a new class of anti-aromatic planar cyclooctatetraenes: the azatrioxa[8]circulenes. This was achieved by treating a suitably functionalised 3,6-dihydroxycarbazole with 1,4-benzoquinones or a 1,4-naphthoquinone. We fully characterised the azatrioxa[8]circulenes by using optical, electrochemical and computational techniques as well as by single-crystal X-ray crystallography. The results of a computational study (NICS) suggest that the central planar cyclooctatetraene is anti-aromatic when the molecules are in neutral or oxidised states (2+), and that the corresponding dianions are aromatic. We discuss the aromatic/anti-aromatic nature of the planar cyclooctatetraenes and compare them with the isoelectronic tetraoxa[8]circulenes.
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