Triptycene
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
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| Preferred IUPAC name
9,10-Dihydro-9,10-[1,2]benzenoanthracene | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.006.837 |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C20H14 | |
| Molar mass | 254.332 g·mol−1 |
| Density | 1.197 g/cm3 |
| Melting point | 252 to 256 °C (486 to 493 °F; 525 to 529 K) |
| Boiling point | 371.8 °C (701.2 °F; 645.0 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.