Formula C20H14 | Molar mass 254.33 g/mol | |
 | ||
Triptycene is an aromatic hydrocarbon, the simplest iptycene molecule with the formula C2H2(C6H4)3. It is a white solid that is soluble in organic solvents. The compound has a paddlewheel configuration with D3h symmetry. Several substituted triptycenes are known. Barrelenes are structurally related.
Contents
Synthesis
The parent triptycene was first prepared in 1942 by a multistep method. It can also be prepared in one step in moderate yields (28%) from the Diels-Alder reaction of anthracene and benzyne. In this method, benzyne is generated by the reaction of magnesium in the presence of 2-bromofluorobenzene.
Derivatives and applications
The hydrocarbon framework is very rigid and triptycene and triptycene derivatives such as triptycene quinones are therefore incorporated in many organic compounds as a molecular scaffold for instance in molecular motors or as a ligand for example in this hydrocyanation:
In this reaction the substrate is butadiene, the reagent acetonecyanohydrine, the catalyst Ni(cod)2 and the ligand a bidentate organophosphine with a large bite angle on a triptycene scaffold.