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 paddle-wheel configuration with D_3h 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]

Triptycene

Names
Preferred IUPAC name 9,10-Dihydro-9,10-[1,2]benzenoanthracene
Identifiers
CAS Number	477-75-8 Y
3D model (JSmol)	Interactive image
ChemSpider	83742 N
ECHA InfoCard	100.006.837
EC Number	207-519-3
PubChem CID	92764
UNII	CL32869MEP Y
CompTox Dashboard (EPA)	DTXSID6060058
InChI InChI=1S/C20H14/c1-2-8-14-13(7-1)19-15-9-3-5-11-17(15)20(14)18-12-6-4-10-16(18)19/h1-12,19-20H N Key: NGDCLPXRKSWRPY-UHFFFAOYSA-N N
SMILES C12=CC=CC=C1C3C5=C(C=CC=C5)C2C4=C3C=CC=C4
Properties
Chemical formula	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). N verify (what is YN ?) Infobox references

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.