Triptycene

 ( Polycyclic Aromatic Hydrocarbons ) 

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 D_3h Symmetry group. It is named after the medieval three-piece art panel, the triptych. Several substituted triptycenes are known. are structurally related. Due to the rigid framework and three-dimensional geometry, derivatives of triptycene have been well researched.

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Synthesis The parent triptycene was first prepared in 1942 by a multistep method. It can also be prepared in one step in 28% yield from the Diels–Alder reaction of anthracene and benzyne. In this method, benzyne is generated by the reaction of magnesium and 2-bromofluorobenzene.

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Derivatives and applications The hydrocarbon framework is very rigid and triptycene derivatives such as triptycene are therefore incorporated in many organic compounds as a molecular scaffold for various applications, such as molecular motors or .

For example, a bis(diphenylphosphino) derivative was used as a phosphine ligand on nickel in a highly selective hydrocyanation reaction of butadiene.

The reactivity of this catalyst is attributed to the large bite angle of the bidentate ligand supported by the triptycene framework.

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External links

• Triptycene MSDS
• Triptycene Dynamic molecular model

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