Cyclooctadeca-1,3,5,7,9,11,13,15,17-nonayne or cyclo 8arbon is an

allotrope of carbon Carbon is capable of forming many allotropy, allotropes (structurally different forms of the same element) due to its Valence (chemistry), valency. Well-known forms of carbon include diamond and graphite. In recent decades, many more allotrope ...

with molecular formula . The molecule is a

ring Ring may refer to: * Ring (jewellery), a round band, usually made of metal, worn as ornamental jewelry * To make a sound with a bell, and the sound made by a bell :(hence) to initiate a telephone connection Arts, entertainment and media Film and ...

of eighteen

carbon Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent In chemistry, the valence (US spelling) or valency (British spelling) of an element is the measure of its combining capacity with o ...

atoms, connected by alternating triple and

single bond In chemistry, a single bond is a chemical bond between two atoms involving two valence electrons. That is, the atoms share one pair of electrons where the bond forms. Therefore, a single bond is a type of covalent bond. When shared, each of th ...

s; thus, it is a

polyyne In organic chemistry, a polyyne () is any organic compound with alternating single and triple bonds; that is, a series of consecutive alkynes, with ''n'' greater than 1. These compounds are also called polyacetylenes, especially in the natural p ...

and a

cyclocarbon In organic chemistry, a cyclo 'n''arbon (or simply cyclocarbon) is a chemical compound consisting solely of a number ''n'' of carbon atoms covalently linked in a ring. Since the compounds are composed only of carbon atoms, they are allotropes of ...

. Cyclo 8arbon is the smallest cyclo 'n''arbon predicted to be

thermodynamically stable In chemistry, chemical stability is the thermodynamic stability of a chemical system. Thermodynamic stability occurs when a system is in its lowest energy state, or in chemical equilibrium with its environment. This may be a dynamic equilibriu ...

, with a computed strain energy of 72 kilocalories per mole. Above 122K, it explosively decomposes to amorphous

graphite Graphite () is a crystalline form of the element carbon. It consists of stacked layers of graphene. Graphite occurs naturally and is the most stable form of carbon under standard conditions. Synthetic and natural graphite are consumed on large ...

. A collaboration of teams at IBM and the

University of Oxford , mottoeng = The Lord is my light , established = , endowment = £6.1 billion (including colleges) (2019) , budget = £2.145 billion (2019–20) , chancellor ...

team claimed to synthesize it in solid state in 2019 by electrochemical

decarbonylation Decarbonylation is a type of organic reaction that involves loss of CO. It is often an undesirable reaction since it represents a degradation. In the chemistry of metal carbonyls, decarbonylation describes a substitution process, whereby a CO lig ...

of several sites of a

cyclobutanone Cyclobutanone is an organic compound with molecular formula (CH2)3CO. It is a four-membered cyclic ketone (cycloalkanone). It is a colorless volatile liquid at room temperature. Since cyclopropanone is highly sensitive, cyclobutanone is the sma ...

structure: Later, researchers from Spain have used computational techniques to probe the structural and electronic properties of the molecule, and have discovered it to be an electron acceptor. Synthese C18

According to these IBM researchers, the electronic structure of their product consists of alternating

triple bond A triple bond in chemistry is a chemical bond between two atoms involving six bonding electrons instead of the usual two in a covalent single bond. Triple bonds are stronger than the equivalent single bonds or double bonds, with a bond order o ...

s and

s, rather than a cumulene-type structure of consecutive double bonds. This supposedly makes this molecule a

semiconductor A semiconductor is a material which has an electrical resistivity and conductivity, electrical conductivity value falling between that of a electrical conductor, conductor, such as copper, and an insulator (electricity), insulator, such as glas ...

References

{{Allotropes of carbon Aromatic compounds Group IV semiconductors Polyynes Cyclocarbons Substances discovered in the 2010s