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
Names
Preferred IUPAC name
Dibenzo[u′v′,a′1b′1]benzo[4′′,10′′]anthra[3′′,2′′,1′′,9′′,8′′:1′,12′,11′,10′]tetrapheno[5′,6′,7′,8′,9′:4,5,6,7]tetraceno[2,1,12,11,10,9-uvwxyza1b1]hexaceno[2,1,16,15,14,13,12,11-defghijklmno:3,4,5,6,7,8,9,10-d′e′f′g′h′i′j′k′l′m′n′o′]diheptacene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C96H30/c1-10-31-37-16-4-22-43-49-28-51-45-24-6-18-39-33-12-2-14-35-41-20-8-26-47-53-30-54-48-27-9-21-42-36-15-3-13-34-40-19-7-25-46-52-29-50-44-23-5-17-38-32(11-1)55(31)70-73(58(37)43)82-64(49)79-66(51)84-75(60(39)45)71(56(33)35)77(62(41)47)86-68(53)81-69(54)87-78(63(42)48)72(57(34)36)76(61(40)46)85-67(52)80-65(50)83(74(70)59(38)44)91(82)94-88(79)95(92(84)86)90(81)96(89(80)94)93(85)87/h1-30H
    Key: GJDYQJRSHRSMEZ-UHFFFAOYSA-N
  • C1=C2C3C4=C5C6=C7C8=C9C%10=C6C=3C3=C6C%11=C%12C(=CC=CC%12=C31)C1=CC=CC3=C1C%11=C1C%11C3=CC=CC=%11C3=CC%11C(=C%12C%13=C%14C(=CC=CC=%11%14)C%11=CC=CC%14=C%11C%13=C%11C%13C%14=CC=CC=%13C%13=CC%14C(=C5C5=C%15C(=CC=CC=%14%15)C%14=CC=CC%15=C%14C5=C4C4C%15=CC=CC2=4)C7=C%13C%11=C%128)C9=C3C1=C6%10
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 overlapping 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. S2CID 39674411.
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