Adamantane

Adamantane

Structure, Nomenclature, and Symmetry of Diamondoids

Published in Sven Stauss, Kazuo Terashima, Diamondoids, 2017

The first diamondoid member is called adamantane, after the Greek word for diamond (αδάμαζ—adámas, “unconquerable,” “indestructible”). Adamantane has the chemical formula C10H16 and consists of a single cage that can be formed by fusing cyclohexanes in chair formation. All the C atoms in the structure of adamantane are C(sp3)–C(sp3)-hybridized, the dangling bonds being terminated by H atoms.

Optical spectrum of the cyanoadamantane radical cation

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Journal Information

Published in Molecular Physics, 2023

Parker B. Crandall, Viktoria D. Lovasz, Robert Radloff, Simone Stahl, Marko Förstel, Otto Dopfer

First discovered in crude oil extracts, diamondoids are a class of aliphatic, caged hydrocarbons that have evolving applications to nanotechnology, medicine, propulsion, and material science due to their remarkable optical and structural properties [14–16]. The simplest diamondoid, adamantane (Ada), consists of three conjoined cyclohexane rings that form a single cage unit. Higher-order diamondoids are constructed with additional cages, the number of which is described in the Greek prefix of the common name (diamantane, triamantane, etc.). Several laboratory investigations have explored the connection between bulk carbon structures and diamondoids as their precursors. Their cage structure makes diamondoid applications highly tuneable, as not only has the size-dependence of the electronic properties of diamonds been studied [17,18] but also the effects of functionalization [19–21].

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Structure, Nomenclature, and Symmetry of Diamondoids

Optical spectrum of the cyanoadamantane radical cation