Triptycene

Chembox new
Name = Triptycene
ImageFileL1 = Triptycene.png ImageSizeL1 = 120px
ImageNameL1 = triptycene
ImageFileR1 = Triptycene3D.png ImageSizeR1 = 150px
Section1 = Chembox Identifiers
CASOther = 477-75-8
SMILES = C12=CC=CC=C1C3C5=C
(C=CC=C5)C2C4=C3C=CC=C4
Section2 = Chembox Properties
Formula = C₂₀H₁₄
MolarMass = 254.33 g/mol
MeltingPt = 252 - 256 °C
BoilingPt =
Density =

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 triptycene and triptycene derivatives such as triptycene quinones ["Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione Spyros Spyroudis" and Nikoletta Xanthopoulou Arkivoc 2003 (vi) 95-105 [http://www.arkat-usa.org/ark/journal/2003/I06_Varvoglis/AV-630A/630A.pdf Online article] ] are therefore incorporated in many organic compounds as a molecular scaffold for instance in molecular motors [cite journal |author=Kelly TR, De Silva H, Silva RA |title=Unidirectional rotary motion in a molecular system |journal=Nature |volume=401 |issue=6749 |pages=150–2 |year=1999 |month=September |pmid=10490021 |doi= |url=http://www.nature.com/nature/journal/v401/n6749/abs/401150a0.html |accessdate=2008-07-16] or as a ligand for example in this hydrocyanation: [cite journal |author=Bini L, Müller C, Wilting J, von Chrzanowski L, Spek AL, Vogt D |title=Highly selective hydrocyanation of butadiene toward 3-pentenenitrile |journal=J. Am. Chem. Soc. |volume=129 |issue=42 |pages=12622–3 |year=2007 |month=October |pmid=17902667 |doi=10.1021/ja074922e |accessdate=2008-07-16] [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]

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References

External links

* [http://newsearchch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?action=PowerSearch&query=msds._msdsID%3D21773&sort=&target=msds&from=0&realQuery=rn.value%3D%3D%22477-75-8%22&searchTemplate=rn.value%3D%3D%3F&searchValue=477-75-8&history=off&options=brandqtyoffer&format=ccd Triptycene MSDS]
* [http://newsearchch.chemexper.com/cheminfo/servlet/org.dbcreator.MainServlet?action=PowerSearch&query=mol3d._mol3dID%3D3778&sort=&target=mol3d&from=0&realQuery=rn.value%3D%3D%22477-75-8%22&searchTemplate=rn.value%3D%3D%3F&searchValue=477-75-8&history=off&options=brandqtyoffer&format=ccd Triptycene Dynamic molecular model]