Harman Patil (Editor)

Triptycene

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Formula
  
C20H14

Molar mass
  
254.33 g/mol

Triptycene httpsuploadwikimediaorgwikipediacommonsthu

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 paddlewheel configuration with D3h symmetry. Several substituted triptycenes are known. Barrelenes are structurally related.

Contents

Triptycene FileTriptycenepng Wikimedia Commons

Synthesis

Triptycene Preparation and characterization of triptycenebased microporous

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

Derivatives and applications

Triptycene Synthesis and characterization of triptycenebased polyimides with

The hydrocarbon framework is very rigid and triptycene and triptycene derivatives such as triptycene quinones are therefore incorporated in many organic compounds as a molecular scaffold for instance in molecular motors or as a ligand for example in this hydrocyanation:

In this reaction the substrate is butadiene, the reagent acetonecyanohydrine, the catalyst Ni(cod)2 and the ligand a bidentate organophosphine with a large bite angle on a triptycene scaffold.

References

Triptycene Wikipedia