Triptycene is an
aromatic hydrocarbon
Aromatic compounds, also known as "mono- and polycyclic aromatic hydrocarbons", are organic compounds containing one or more aromatic rings. The parent member of aromatic compounds is benzene. The word "aromatic" originates from the past grou ...
, the simplest
iptycene
An iptycene is an aromatic compound composed of varying number of arene subunits bound to a bridged bicyclo-octatriene core structure. They are formally derivatives of barrelene. The first and simplest iptycene molecule is triptycene.
The first ...
molecule with the formula C
2H
2(C
6H
4)
3. It is a white solid that is soluble in organic solvents. The compound has a
paddle-wheel
A paddle wheel is a form of waterwheel or impeller in which a number of paddles are set around the periphery of the wheel. It has several uses, of which some are:
* Very low-lift water pumping, such as flooding paddy fields at no more than abo ...
configuration with D
3h symmetry. It is named after the medieval three-piece art panel, the
triptych
A triptych ( ; from the Greek adjective ''τρίπτυχον'' "''triptukhon''" ("three-fold"), from ''tri'', i.e., "three" and ''ptysso'', i.e., "to fold" or ''ptyx'', i.e., "fold") is a work of art (usually a panel painting) that is divide ...
.
[ Several substituted triptycenes are known. ]Barrelene
Barrelene is a bicyclic organic compound with chemical formula C8H8 and systematic name bicyclo .2.2cta-2,5,7-triene. First synthesized and described by Howard Zimmerman in 1960, the name derives from the resemblance to a barrel, with the staves ...
s 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.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 ...
of 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. Anthracene is ...
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
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...
as a molecular scaffold
A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioche ...
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 ( 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 ele ...
s.
For example, a bis(diphenylphosphino) derivative was used as a phosphine ligand A metal-phosphine complex is a In coordination complex containing one or more phosphine ligands. Almost always, the phosphine is an organophosphine of the type R3P (R = alkyl, aryl). Metal phosphine complexes are useful in homogeneous catalysis. P ...
on nickel
Nickel is a chemical element with 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 slow ...
in a highly selective hydrocyanation
In organic chemistry, hydrocyanation is a process for conversion of alkenes to nitriles. The reaction involves the addition of hydrogen cyanide and requires a catalyst. This conversion is conducted on an industrial scale for the production of pr ...
reaction of butadiene
1,3-Butadiene () is the organic compound with the formula (CH2=CH)2. 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 vin ...
.bite angle
In coordination chemistry the bite angle is the ligand–metal–ligand bond angle of coordination complex containing a bidentate ligand. This geometric parameter is used to classify chelating ligands, including those in organometallic complex ...
of the bidentate ligand supported by the triptycene framework.
References
{{reflist
External links
Triptycene MSDS
Triptycene Dynamic molecular model
Polycyclic aromatic hydrocarbons