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Triptycene

Triptycene
Chemical name	9,10-o-Benzeno-9,10 -dihydroanthracene
Chemical formula	C₂₀H₁₄
Molecular mass	254.33 g/mol
Melting point	252 - 256 °C
Boiling point	°C
Density	g/cm³
CAS number	477-75-8
SMILES	C12=CC=CC=C1C3C5=C (C=CC=C5)C2C4=C3C=CC=C4

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Triptycenes are a class of aromatic hydrocarbons. The parent compound triptycene is the Diels-Alder reaction product of anthracene and benzyne. The compound has a paddlewheel configuration with D_3h symmetry. Barrelenes are conceptually related compounds. The hydrocarbon framework is very rigid and is therefore incorporated in many organic compounds as a molecular scaffold for instance in molecular motors ^[1] or as a ligand for example in this hydrocyanation ^[2] ^[3]:

References

^ Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione Spyros Spyroudis and Nikoletta Xanthopoulou Arkivoc 2003 (vi) 95-105 Online article
^ Highly Selective Hydrocyanation of Butadiene toward 3-Pentenenitrile Bini, L.; Muller, C.; Wilting, J.; von Chrzanowski, L.; Spek, A. L.; Vogt, D. J. Am. Chem. Soc.; (Communication); 2007; 129(42); 12622-12623. doi:10.1021/ja074922e
^ 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 trypticene scaffold