Triptycene is an
aromatic hydrocarbon, 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 configuration with D
3h symmetry
Symmetry (from grc, συμμετρία "agreement in dimensions, due proportion, arrangement") in everyday language refers to a sense of harmonious and beautiful proportion and balance. In mathematics, "symmetry" has a more precise definit ...
. It is named after the medieval three-piece art panel, the
triptych.
[ 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.Diels–Alder reaction
In organic chemistry, the Diels–Alder reaction is a chemical reaction between a conjugated diene and a substituted alkene, commonly termed the dienophile, to form a substituted cyclohexene derivative. It is the prototypical example of a peric ...
of anthracene 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 uch as benzene or naphthalene
Uch ( pa, ;
ur, ), frequently referred to as Uch Sharīf ( pa, ;
ur, ; ''"Noble Uch"''), is a historic city in the southern part of Pakistan's Punjab province. Uch may have been founded as Alexandria on the Indus, a town founded by Alexand ...
by conversion of an even number of –CH= groups into –C(=O)– groups with any necessary rearrangement of double ...
s are therefore incorporated in many organic compounds 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 motors or ligands.
For example, a bis(diphenylphosphino) derivative was used as a phosphine ligand on nickel in a highly selective hydrocyanation reaction of butadiene.
References
{{reflist
External links
Triptycene MSDS
Triptycene Dynamic molecular model
Polycyclic aromatic hydrocarbons