Triptycene
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 D3hsymmetry. Several substituted triptycenes are known. Barrelenes are structurally related.
Synthesis
The parent triptycene was first prepared in 1942 by a multistep method. It can be prepared in one step from the Diels-Alder reaction of anthracene and benzyne. The benzyne is generated by the reaction of magnesium in the presence of 2-bromofluorobenzene. Triptycene forms in modest yield this conversion is conducted in the presence of the anthracene.
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.
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