Circumcoronene

Circumcoronene is a polycyclic aromatic hydrocarbon with the molecular formula C₅₄H₁₈. It consists of a central coronene molecule circumscribed by benzene on the periphery.

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Circumcoronene

Names
IUPAC name nonadecacyclo[27.23.1.14,44.06,43.09,42.011,40.014,39.016,37.019,36.021,34.024,33.026,31.030,51.032,49.035,48.038,47.041,46.045,50.052,54]tetrapentaconta-1(53),2,4,6(43),7,9,11(40),12,14,16(37),17,19(36),20,22,24(33),25,27,29,31,34,38,41,44,46,48,50,52(54)-heptacosaene
Other names Circumcoronene Dodecabenzocoronene Coronene 19 Tripyreno[2,1,10,9,8,7-defghij:2′,1′,10′,9′,8′,7′-nopqrst:2′′,1′′,10′′,9′′,8′′,7′′-xyza1b1c1d1]trinaphthylene
Identifiers
CAS Number	72210-95-8
3D model (JSmol)	Interactive image
Beilstein Reference	2495518
ChEBI	CHEBI:51386
ChemSpider	21865866
Gmelin Reference	2653231
PubChem CID	25137954
CompTox Dashboard (EPA)	DTXSID301108666
InChI InChI=1S/C54H18/c1-2-20-14-22-5-6-24-16-26-9-11-29-18-30-12-10-28-17-27-8-7-25-15-23-4-3-21-13-19(1)31-32(20)44-34(22)36(24)46-39(26)41(29)48-42(30)40(28)47-38(27)37(25)45-35(23)33(21)43(31)49-50(44)52(46)54(48)53(47)51(45)49/h1-18H Key: ICKDBJSKNOTKDQ-UHFFFAOYSA-N
SMILES c1cc2cc3ccc4cc5ccc6cc7ccc8cc9ccc%10cc%11ccc%12cc1c1c2c2c3c4c3c5c6c4c7c8c5c9c%10c6c%11c%12c1c1c2c3c4c5c61
Properties
Chemical formula	C54H18
Molar mass	666.738 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

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Circumcoronene is the third benzenoid hydrocarbon in the benzene-coronene-circumcoronene series. It comes after benzene and coronene, and is followed by circumcircumcoronene. Various topological and mathematical properties have been computed for molecules in this series.^[1][2]

On-surface synthesis of circumcoronene was achieved in 2021 via intramolecular dehydrogenation of a precursor hexa-peri-hexabenzocoronene, followed by methyl radical coupling and aromatization, on a Cu(111) surface.^[3] A solution-phase synthesis was reported in 2023 via acid-mediated cyclization of alkynes, confirmed via X-ray crystallographic analysis and NMR measurement.^[4]