Triptycene
| |
| |
| Names | |
|---|---|
| Preferred IUPAC name
9,10-Dihydro-9,10-[1,2]benzenoanthracene | |
| Identifiers | |
3D model (
JSmol ) |
|
| ChemSpider | |
ECHA InfoCard
|
100.006.837 |
| EC Number |
|
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| 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).
| |
Triptycene is an
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.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
.For example, a bis(diphenylphosphino) derivative was used as a
The reactivity of this catalyst is attributed to the largebidentate
ligand supported by the triptycene framework.