Diamonds are a Chemist's Best Friend: Diamondoid Chemistry Beyond Adamantane

Abstract

Marilyn Monroe knew that "diamonds are a girl's best friend" but, in the meantime, many chemists have realized that they are also extremely attractive objects in contemporary chemistry. The chemist's diamonds are usually quite small (herein: nanometer-sized "diamondoids") and as a result of their unique structure are unusual chemical building blocks. Since lower diamondoids (up to triamantane) have recently become available in large amounts from petroleum and higher diamondoids (starting from tetramantane) are now also accessible from crude oil new research involving them has begun to emerge. Having well-defined structures makes these cage compounds so special compared to other nanometer-scale diamonds. Selective and high-yielding synthetic approaches to the functionalization of diamondoids gives derivatives that can find applications in, for example, polymers, coating materials, drugs, and molecular electronics.

Laser-induced fluorescence of free diamondoid molecules

“…Size-and shape-selected neutral diamondoids in the gas phase are optimal model systems for theory, especially for the study of quantum confinement effects. [20][21][22][23][24][25] In particular, doped or surface-modified diamondoids [2][3][4][5][6] as well as diamondoid dimers or trimers are extremely attractive as nanoscale building blocks for applications. Another interesting feature is the photoluminescence of diamondoids.…”

Near-Edge X-ray Absorption Fine Structure Spectroscopy of Diamondoid Thiol Monolayers on Gold

“…The lower diamondoids, with three or fewer diamond cages, are adamantane, diamantane, and triamantane. Higher diamondoids, nanometer-sized diamond molecules with greater than three diamond cages, have largely evaded laboratory synthesis 1 and have only recently been purified from petroleum sources 2 . These diamondoids exhibit a variety of isomeric structures.…”

Hypercohones A–C, acylphloroglucinol derivatives with homo-adamantane cores from Hypericum cohaerens

“…1,2 In the past 50 years, adamantanes have yielded many compounds directed toward many different drug targets. Based on our detailed literature research, the adamantyl group was present in seven registered therapeutic compounds used currently for clinical use, and in many more compounds that were currently being developed as potential agents for the treatment of conditions such as iron overload disease, cancer, malaria and tuberculosis.…”

“…memantine and amantadine), or as a modifier of the pharmacokinetics of a compound. [1][2][3][4] It was once assumed that living organisms could not synthesize adamantane derivatives, whose synthesis was considered purely abiotic. This view was finally refuted in 1996 when pukenetione A, the first adamantane derivative isolated and identified from the plant Clusia plukenetii (Guttiferae).…”