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Circulene

from Wikipedia, the free encyclopedia

Circulene, also called corannulene, are aromatic hydrocarbons. The structuring element of the circulenes is that the cyclic aromatics themselves form a cyclic compound. Circulenes can be composed of aromatics as well as heteroaromatics

For the nomenclature of simple circulenes, the number of aromatic rings is prefixed in square brackets. Thus the systematic designation of corannulene is [5]-circulene, of coronene [6]-circulene.

Structure

Circulene is divided into an inner and an outer perimeter. Both perimeters form through-conjugated systems which, depending on the number of electrons, can have both aromatic and antiaromatic character.

Division of the Circulene into inner perimeter (blue) and outer perimeter (red).

The coupling between the two parameters depends on the system considered. A strong coupling between both perimeters is possible, which corresponds to the main mesomerism within the individual aromatics, and a weak coupling, which corresponds to the separate presence of an inner and an outer aromatic system.

Strong (left) and weak coupling (right) between perimeters

Sources

  • H. R. Christen, F. Vögtle: Organische Chemie – Von den Grundlagen zur Forschung. 2. Auflage, S. 422-433, Otto Salle Verlag, Frankfurt a. Main 1996, ISBN 3-7935-5398-1.