Circulene

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[7]circulene

A circulene is a

synthesized include [5]circulene (corannulene), [6]circulene (coronene), [7]circulene,[2][3][4][5] and [12]circulene (kekulene) These compounds belong to a larger class of geodesic polyarenes. Whereas [5]circulene is bowl-shaped and [6]circulene is planar, [7]circulene has a unique saddle-shaped structure (compare to cones and partial cones in calixarenes). The helicenes are a conceptually related class of structures in which the array of benzene rings form an open helix
rather than a closed ring.

Quadrannulene ([4]circulene)

The simple [4]circulene compound itself has not been synthesized, but a derivative, tetrabenzo[4]circulene, also called quadrannulene, has.[6]

[8]Circulenes

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]

Heterocyclic circulenes

Sulflower, an octacirculene

A

heterocyclic 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 on thiophene
.

Gallery

References

  1. doi:10.1016/S0040-4039(01)84432-4
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  2. doi:10.1021/ja00362a025
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  3. doi:10.1021/ja00219a036
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  4. doi:10.1002/anie.199600691
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  5. ^ 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
  6. PMID 19957259
    .
  7. PMID 23794166
    .
  8. PMID 24615957
    .
  9. PMID 24015972
    .
  10. PMID 27934450
    .
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