Triptycene

Triptycene
Names
	Preferred IUPAC name 9,10-Dihydro-9,10-[1,2]benzenoanthracene
Identifiers
CAS Number	477-75-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	83742 ;
ECHA InfoCard	100.006.837
EC Number	207-519-3;
PubChem CID	92764;
UNII	CL32869MEP ;
CompTox Dashboard (EPA)	DTXSID6060058 ;
	InChI InChI=1S/C20H14/c1-2-8-14-13(7-1)19-15-9-3-5-11-17(15)20(14)18-12-6-4-10-16(18)19/h1-12,19-20H Key: NGDCLPXRKSWRPY-UHFFFAOYSA-N ;
	SMILES C12=CC=CC=C1C3C5=C(C=CC=C5)C2C4=C3C=CC=C4;
Properties
Chemical formula	C20H14
Molar mass	254.332 g·mol−1
Melting point	252 to 256 °C (486 to 493 °F; 525 to 529 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

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 D_3h symmetry. It is named after the medieval three-piece art panel, the triptych.[1] 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.[2]

Synthesis

The parent triptycene was first prepared in 1942 by a multistep method.[1] It can also be prepared in one step in 28% yield from the Diels–Alder reaction of anthracene and benzyne.[3] 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 quinones[4] are therefore incorporated in many organic compounds as a molecular scaffold for various applications, such as molecular motors[5] or ligands.

For example, a bis(diphenylphosphino) derivative was used as a phosphine ligand on nickel in a highly selective hydrocyanation reaction of butadiene:[6] The reactivity of this catalyst is attributed to the large bite angle of the bidentate ligand supported by the triptycene framework.

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References

Bartlett, Paul D.; Ryan, M. Josephine; Cohen, Saul G. (1942). "Triptycene1 (9,10-o-Benzenoanthracene)". J. Am. Chem. Soc. 64 (11): 2649–2653. doi:10.1021/ja01263a035.
Zhao, Liwei; Li, Zhong; Wirth, Thomas (2010). "Triptycene Derivatives: Synthesis and Applications". Chemistry Letters. 39 (7): 658–667. doi:10.1246/cl.2010.658.
Wittig, George (1959). "Triptycene". Org. Synth. 39: 75. doi:10.15227/orgsyn.039.0075.
Spyroudis S, Xanthopoulou N (2003). "Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione" (PDF). Arkivoc. 2003 (vi): 95–105. doi:10.3998/ark.5550190.0004.612.
Kelly TR, De Silva H, Silva RA (September 1999). "Unidirectional rotary motion in a molecular system". Nature. 401 (6749): 150–152. doi:10.1038/43639. PMID 10490021.
Bini L, Müller C, Wilting J, von Chrzanowski L, Spek AL, Vogt D (October 2007). "Highly selective hydrocyanation of butadiene toward 3-pentenenitrile". J. Am. Chem. Soc. 129 (42): 12622–12623. doi:10.1021/ja074922e. hdl:1874/26892. PMID 17902667.

External links

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[Bartlett-1] Bartlett, Paul D.; Ryan, M. Josephine; Cohen, Saul G. (1942). "Triptycene1 (9,10-o-Benzenoanthracene)". J. Am. Chem. Soc. 64 (11): 2649–2653. doi:10.1021/ja01263a035.

[2] Zhao, Liwei; Li, Zhong; Wirth, Thomas (2010). "Triptycene Derivatives: Synthesis and Applications". Chemistry Letters. 39 (7): 658–667. doi:10.1246/cl.2010.658.

[3] Wittig, George (1959). "Triptycene". Org. Synth. 39: 75. doi:10.15227/orgsyn.039.0075.

[4] Spyroudis S, Xanthopoulou N (2003). "Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione" (PDF). Arkivoc. 2003 (vi): 95–105. doi:10.3998/ark.5550190.0004.612.

[5] Kelly TR, De Silva H, Silva RA (September 1999). "Unidirectional rotary motion in a molecular system". Nature. 401 (6749): 150–152. doi:10.1038/43639. PMID 10490021.

[6] Bini L, Müller C, Wilting J, von Chrzanowski L, Spek AL, Vogt D (October 2007). "Highly selective hydrocyanation of butadiene toward 3-pentenenitrile". J. Am. Chem. Soc. 129 (42): 12622–12623. doi:10.1021/ja074922e. hdl:1874/26892. PMID 17902667.