Triptycene
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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 paddle-wheel configuration with D3h symmetry. It is named after the medieval three-piece art panel, the triptych.[1] Several substituted triptycenes are known. Barrelenes are structurally related. Due to the rigid framework and three-dimensional geometry, derivatives of triptycene have been well researched.[2]
Synthesis
The parent triptycene was first prepared in 1942 by a multistep method.[1] It can also be prepared in one step in 28% yield from the Diels–Alder reaction of anthracene and benzyne.[3] In this method, benzyne is generated by the reaction of magnesium and 2-bromofluorobenzene.
Derivatives and applications
The hydrocarbon framework is very rigid and triptycene derivatives such as triptycene quinones[4] are therefore incorporated in many organic compounds as a molecular scaffold for various applications, such as molecular motors[5] or ligands.
For example, a bis(diphenylphosphino) derivative was used as a phosphine ligand on nickel in a highly selective hydrocyanation reaction of butadiene.[6] The reactivity of this catalyst is attributed to the large bite angle of the bidentate ligand supported by the triptycene framework.