Triptycene is an

aromatic hydrocarbon Aromatic compounds or arenes are organic compounds "with a chemistry typified by benzene" and "cyclically conjugated." The word "aromatic" originates from the past grouping of molecules based on odor, before their general chemical properties were ...

, 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 Symmetry () in everyday life refers to a sense of harmonious and beautiful proportion and balance. In mathematics, the term has a more precise definition and is usually used to refer to an object that is Invariant (mathematics), invariant und ...

. It is named after the medieval three-piece art panel, the

triptych A triptych ( ) is a work of art (usually a panel painting) that is divided into three sections, or three carved panels that are hinged together and can be folded shut or displayed open. It is therefore a type of polyptych, the term for all m ...

. 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.

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 In organic chemistry, the Diels–Alder reaction is a chemical reaction between a Conjugated system, conjugated diene and a substituted alkene, commonly termed the Diels–Alder reaction#The dienophile, dienophile, to form a substituted cyclohexe ...

anthracene Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes, as a scintil ...

and benzyne. 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

quinone The quinones are a class of organic compounds that are formally "derived from aromatic compounds benzene.html" ;"title="uch as benzene">uch as benzene or naphthalene] by conversion of an even number of –CH= groups into –C(=O)– groups with ...

s are therefore incorporated in many

organic compounds Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

as a molecular scaffold for various applications, such as

molecular motor Molecular motors are natural (biological) or artificial molecular machines that are the essential agents of movement in living organisms. In general terms, a motor is a device that consumes energy in one form and converts it into motion or mech ...

s or

ligand In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...

s. For example, a bis(diphenylphosphino) derivative was used as a phosphine ligand on

nickel Nickel is a chemical element; it has symbol Ni and atomic number 28. It is a silvery-white lustrous metal with a slight golden tinge. Nickel is a hard and ductile transition metal. Pure nickel is chemically reactive, but large pieces are slo ...

in a highly selective hydrocyanation reaction of

butadiene 1,3-Butadiene () is the organic compound with the formula CH2=CH-CH=CH2. It is a colorless gas that is easily condensed to a liquid. It is important industrially as a precursor to synthetic rubber. The molecule can be viewed as the union of two ...

. The reactivity of this catalyst is attributed to the large

bite angle In coordination chemistry, the bite angle is the angle on a central atom between two bonds to a bidentate ligand. This ligand–metal–ligand geometric parameter is used to classify chelation, chelating ligands, including those in organometallic ...

of the bidentate ligand supported by the triptycene framework.

References

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External links

Triptycene MSDS

Triptycene Dynamic molecular model
Polycyclic aromatic hydrocarbons