:Triptycene
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{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 445765631
| Name = Triptycene
| ImageFile = Triptycene.svg
| ImageSize = 180px
| ImageAlt = Skeletal formula
| ImageFile1 = Triptycene-3D-spacefill.png
| ImageSize1 = 180px
| ImageAlt1 = Space-filling model
| PIN = 9,10-Dihydro-9,10-[1,2]benzenoanthracene
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 477-75-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = CL32869MEP
| PubChem = 92764
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 83742
| EINECS = 207-519-3
| SMILES = C12=CC=CC=C1C3C5=C(C=CC=C5)C2C4=C3C=CC=C4
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = NGDCLPXRKSWRPY-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C = 20
| H = 14
| MeltingPtC = 252 to 256
| BoilingPtC = 371.8
| Density = 1.197 g/cm3
}}
}}
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.{{Cite journal|doi=10.1246/cl.2010.658|title = Triptycene Derivatives: Synthesis and Applications|journal = Chemistry Letters|volume = 39|issue = 7|pages = 658–667|year = 2010|last1 = Zhao|first1 = Liwei|last2 = Li|first2 = Zhong|last3 = Wirth|first3 = Thomas}}
Synthesis
The parent triptycene was first prepared in 1942 by a multistep method.{{cite journal | last1 = Bartlett | first1 = Paul D. |author1-link= Paul Doughty Bartlett | last2 = Ryan | first2 = M. Josephine | last3 = Cohen | first3 = Saul G. | year = 1942 | title = Triptycene (9,10-o-Benzenoanthracene) | journal = J. Am. Chem. Soc. | volume = 64 | issue = 11 | pages = 2649–2653 | doi = 10.1021/ja01263a035 }} It can also be prepared in one step in 28% yield from the Diels–Alder reaction of anthracene and benzyne.{{cite journal | last1 = Wittig | first1 = George | year = 1959 | title = Triptycene | journal = Org. Synth. | volume = 39 | page = 75 | doi = 10.15227/orgsyn.039.0075 }} 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{{ cite journal | title = Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione |vauthors=Spyroudis S, Xanthopoulou N | journal = Arkivoc | year = 2003 | volume = 2003 | issue = vi | pages = 95–105 | url = http://www.arkat-usa.org/ark/journal/2003/I06_Varvoglis/AV-630A/630A.pdf |doi=10.3998/ark.5550190.0004.612 | doi-access = free }} are therefore incorporated in many organic compounds as a molecular scaffold for various applications, such as molecular motors{{cite journal |vauthors=Kelly TR, De Silva H, Silva RA | title = Unidirectional rotary motion in a molecular system | journal = Nature | volume = 401 | issue = 6749 | pages = 150–152 |date=September 1999 | pmid = 10490021 | doi = 10.1038/43639 | bibcode = 1999Natur.401..150K | s2cid = 4351615 }} or ligands.
For example, a bis(diphenylphosphino) derivative was used as a phosphine ligand on nickel in a highly selective hydrocyanation reaction of butadiene.{{cite journal |vauthors=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 = 12622–12623 |date=October 2007 | pmid = 17902667 | doi = 10.1021/ja074922e | hdl = 1874/26892 | hdl-access = free }}
The reactivity of this catalyst is attributed to the large bite angle of the bidentate ligand supported by the triptycene framework.
References
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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]