Acirculene is amacrocyclicarene in which a centralpolygon is surrounded andfused bybenzenoids.[1] Nomenclature within this class of molecules is based on the number of benzene rings surrounding the core, which is equivalent to the size of the central polygon. Examples which have beensynthesized include [5]circulene (corannulene), [6]circulene (coronene), [7]circulene,[2][3][4][5] and [12]circulene (kekulene) These compounds belong to a larger class ofgeodesic polyarenes. Whereas [5]circulene is bowl-shaped and [6]circulene is planar, [7]circulene has a uniquesaddle-shaped structure (compare to cones and partial cones incalixarenes). Thehelicenes are a conceptually related class of structures in which the array of benzene rings form an openhelix rather than a closed ring.
The isolation of the[8]circulene derivative 2,5,6,9,10,13,14-octamethyl-3,4,7,8,11,12,15,16-octa(4-tolyl)[8]circulene has been reported.[7]Tetrabenzo[8]circulene (TB8C), a functionally stable form of the parent molecule [8]circulene has also been reported.[8][9][10]
Aheterocyclic circulene is one in which the fused rings around the periphery are not simple hydrocarbons, but instead contain at least one other element.Sulflower is a stable heterocyclic octacirculene based onthiophene.
^Dopper, J.H.; Wynberg, Hans (1972). "Heterocirculenes a new class of polycyclic aromatic hydrocarbons".Tetrahedron Letters.13 (9):763–766.doi:10.1016/S0040-4039(01)84432-4.
^Yamamoto, Koji; Harada, Tadashi; Nakazaki, Masao; Naka, Takuo; Kai, Yasushi; Harada, Shigeharu; Kasai, Nobutami (1983). "Synthesis and characterization of [7]circulene".Journal of the American Chemical Society.105 (24):7171–7172.doi:10.1021/ja00362a025.
^Koji, Yamamoto; Tadashi, Harada; Yoshio, Okamoto; Hiroaki, Chikamatsu; Masao, Nakazaki; Yasushi, Kai; Takuo, Nakao; Mitsuya, Tanaka; Shigeharu, Harada; Nobutami, Kasai (1988). "Synthesis and molecular structure of [7]circulene".Journal of the American Chemical Society.110 (11):3578–3584.doi:10.1021/ja00219a036.
^Yamamoto, K.; Sonobe, H.; Matsubara, H.; Sato, M.; Okamoto, S.; Kitaura, K. (1996). "Convenient New Synthesis of [7]Circulene".Angew. Chem. Int. Ed. Engl.35:69–70.doi:10.1002/anie.199600691.
^Extended systems of closed helicene. Synthesis and characterization of [7] and [7.7]-circulene Koji Yamamoto Pure Appl. Chem., Vol. 65, No. 1, pp. 157-163,1993.Online article
^Miller, Robert W.; Averill, Summer E.; Van Wyck, Stephen J.; Whalley, Adam C. (2 December 2016). "General Method for the Synthesis of Functionalized Tetrabenzo[8]circulenes".The Journal of Organic Chemistry.81 (23): 12005.doi:10.1021/acs.joc.6b02244.PMID27934450.