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 D3h symmetry. 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.

Chemical data

Formula: C20H14
Molecular weight: 254.3 g/mol
IUPAC name: pentacyclo[6.6.6.02,7.09,14.015,20]icosa-2,4,6,9,11,13,15,17,19-nonaene
SMILES: C1=CC=C2C3C4=CC=CC=C4C(C2=C1)C5=CC=CC=C35
InChIKey: NGDCLPXRKSWRPY-UHFFFAOYSA-N
XLogP: 4.8
Polar surface area: 0 Å²
H-bond donors: 0
H-bond acceptors: 0
Formal charge: 0

via PubChem

Wikidata facts

Subclass of: chemical compound
Has part: hydrogen
Mass: 254.11

Show 3 more facts

chemical formula: C₂₀H₁₄
Commons category: Triptycene
canonical SMILES: C1=CC=C2C3C4=CC=CC=C4C(C2=C1)C5=CC=CC=C35

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Encyclopedic overview

4 sections

Contents

Synthesis
Derivatives and applications
References
External links

==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 of anthracene and benzyne. In this method, benzyne is generated by the reaction of magnesium and 2-bromofluorobenzene.

Excerpted from Wikipedia’s “triptycene” article, available under the CC BY-SA 4.0 licence.