Superphenalene

Superphenalene is a very large polycyclic aromatic hydrocarbon (PAH) with chemical formula C96H30. It can be formally considered to consist of three fused superbenzenes (hexa-peri-hexabenzocoronene).[1]

Superphenalene

Chemical structure of superphenalene
Identifiers
Properties
C96H30
Molar mass 1183.296 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It can be considered as an overlap structure of three hexa-peri-hexabenzocoronenes arranged symmetrically around a center.[2][3] These have also been known as building blocks of molecular electronics since 2004 as they form self-assembling columns and nanotubes.[4]

Occurrence

It is not known to occur naturally.

Properties
Planar geometry of superphenalene

Superphenalene has a planar geometry. With 540,000 mesomeric boundary structures, it has significantly more than hexabenzocoronene (250), supernaphthalene (16,100) and also buckminsterfullerene (12,500).[1] The molecule has a threefold symmetry axis perpendicular to the molecule (C3).

References
  1. Randić, Milan; Gao, Xiaofeng (1999). "Giant benzenoid hydrocarbons. Superphenalene resonance energy". New Journal of Chemistry. 23 (2): 251–260. doi:10.1039/A808949C.
  2. Ito, Shunji; Herwig, Peter Tobias; Böhme, Thilo; Rabe, Jürgen P.; Rettig, Wolfgang; Müllen, Klaus (2000). "Bishexa-peri-hexabenzocoronenyl: A "Superbiphenyl"". Journal of the American Chemical Society. 122 (32): 7698–7706. doi:10.1021/ja000850e.
  3. Wu, Jishan; Watson, Mark D.; Tchebotareva, Natalia; Wang, Zhaohui; Müllen, Klaus (2004). "Oligomers of Hexa-peri-hexabenzocoronenes as "Super-oligophenylenes": Synthesis, Electronic Properties, and Self-assembly". The Journal of Organic Chemistry. 69 (24): 8194–8204. doi:10.1021/jo0490301. PMID 15549787.
  4. Hill, J. P.; Jin, W.; Kosaka, A.; Fukushima, T.; Ichihara, H.; Shimomura, T.; Ito, K.; Hashizume, T.; Ishii, N.; Aida, T. (2004). "Self-Assembled Hexa-peri-hexabenzocoronene Graphitic Nanotube". Science. 304 (5676): 1481–1483. Bibcode:2004Sci...304.1481H. doi:10.1126/science.1097789. PMID 15178796.
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