{{cs1 config|name-list-style=vanc}} {{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/cm<sup>3</sup> }} }}
'''Triptycene''' is an aromatic hydrocarbon, the simplest iptycene molecule with the formula C<sub>2</sub>H<sub>2</sub>(C<sub>6</sub>H<sub>4</sub>)<sub>3</sub>. It is a white solid that is soluble in organic solvents. The compound has a paddle-wheel configuration with D<sub>3h</sub> symmetry. It is named after the medieval three-piece art panel, the triptych.<ref name=Bartlett/> 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.<ref>{{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}}</ref>
==Synthesis== The parent triptycene was first prepared in 1942 by a multistep method.<ref name=Bartlett>{{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 }}</ref> It can also be prepared in one step in 28% yield from the Diels–Alder reaction of anthracene and benzyne.<ref>{{cite journal | last1 = Wittig | first1 = George | year = 1959 | title = Triptycene | journal = Org. Synth. | volume = 39 | page = 75 | doi = 10.15227/orgsyn.039.0075 }}</ref> 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<ref>{{ 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 }}</ref> are therefore incorporated in many organic compounds as a molecular scaffold for various applications, such as molecular motors<ref>{{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 }}</ref> or ligands.
For example, a bis(diphenylphosphino) derivative was used as a phosphine ligand on nickel in a highly selective hydrocyanation reaction of butadiene.<ref>{{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 }}</ref> <!--:500px|Use of trypticene in catalysts ligands--> The reactivity of this catalyst is attributed to the large bite angle of the bidentate ligand supported by the triptycene framework.
==References== {{reflist}}
==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]
Category:Polycyclic aromatic hydrocarbons