Diamondoids: functionalization and subsequent applications of perfectly defined molecular cage hydrocarbons

Abstract

The term “diamondoid” describes cage hydrocarbon molecules that are superimposable on the diamond lattice. Diamondoids that are formally built by face-fusing of adamantane units, namely diamantane, triamantane, tetramantane, etc., have fascinated chemists since the beginning of the last century. The functionalization of these perfectly defined (C,H)-molecules is described here. Thus, diamondoid halides and diamondoid alcohols are first rank precursors for amino and phosphine-substituted diamondoids that have proved to be highly useful in therapeutic applications and metal catalysis, respectively. The extent of functionalization and polyfunctionalization achieved for adamantane and diamantane, and the synthesis and applications of the resulting organohybrids are illustrated, revealing their high potential in fields such as organocatalysis, polymers, molecular electronics and mechanics.