# Triptycene

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> Markdown URL: https://mediated.wiki/source/Triptycene.md
> Source: https://en.wikipedia.org/wiki/Triptycene
> Source revision: 1211204874
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{{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](/source/aromatic_hydrocarbon), the simplest [iptycene](/source/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](/source/paddle-wheel) configuration with D<sub>3h</sub> [symmetry](/source/Symmetry_group).  It is named after the medieval three-piece art panel, the [triptych](/source/triptych).<ref name=Bartlett/>  Several substituted triptycenes are known.  [Barrelene](/source/Barrelene)s 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](/source/Diels%E2%80%93Alder_reaction) of [anthracene](/source/anthracene) and [benzyne](/source/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 [quinone](/source/quinone)s<ref>{{ cite journal | title = Triptycene quinones in synthesis: preparation of triptycene bis-cyclopentenedione |vauthors=Spyroudis S, Xanthopoulou N | journal = [Arkivoc](/source/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](/source/organic_compounds) as a [molecular scaffold](/source/molecular_scaffold) for various applications, such as [molecular motor](/source/Synthetic_molecular_motors)s<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 [ligand](/source/ligand)s.

For example, a bis(diphenylphosphino) derivative was used as a [phosphine ligand](/source/phosphine_ligand) on [nickel](/source/nickel) in a highly selective [hydrocyanation](/source/hydrocyanation) reaction of [butadiene](/source/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](/source/bite_angle) of the [bidentate](/source/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

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Adapted from the Wikipedia article [Triptycene](https://en.wikipedia.org/wiki/Triptycene) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Triptycene?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.