View source for Acene

[[Image:Acenes general structure.svg|thumb|The general structural formula for acenes]]

'''Acenes''' (sometimes referred to as '''polyacenes''') form a [[functional class]] of [[organic compound]]s: they are [[polycyclic aromatic hydrocarbon]]s  made up of linearly fused benzene rings.<ref>{{IUPAC class names 1995|page=1310}}.</ref>  The larger acenes have potential interest in optoelectronic applications and as [[organic semiconductor]]s.<ref name="Antony">{{citation | last1 = Anthony | first1 = John  E. | year = 2008 | title = The Larger Acenes: Versatile Organic Semiconductors | journal = Angew. Chem., Int. Ed. Engl. | volume = 47 | issue = 3 | pages = 452–83 | doi = 10.1002/anie.200604045}}.</ref><ref name="Zade">{{citation | last1 = Zade | first1 = Sanjio S. | last2 = Bendikov | first2 = Michael | title = Heptacene and Beyond: the Longest Characterized Acenes | journal = Angew. Chem., Int. Ed. Engl. | year = 2010 | volume = 49 | issue = 24 | pages = 1012–15 | doi = 10.1002/anie.200906002}}.</ref> [[Pentacene]] has been incorporated into [[organic field-effect transistor]]s, reaching charge carrier mobilities as high as {{nowrap|5 cm<sup>2</sup> V<sup>−1</sup> s<sup>−1</sup>}}.<ref name="Antony"/> Unsubstituted acenes larger than pentacene have only been studied by [[matrix isolation]] techniques,<ref name="Antony"/><ref name="Zade"/><ref>{{citation | last1 = Tönshoff | first1 = Christina | last2 = Bettinger | first2 = Holger F. | title = Photogeneration of Octacene and Nonacene | journal = Angew. Chem. Int. Ed. Engl. | year = 2010 | volume = 49 | issue = 24 | pages = 4125–28 | doi = 10.1002/anie.200906355}}.</ref> although substituted acenes up to nonacene have been isolated.<ref name="Antony"/><ref>{{citation | last1 = Kaur | first1 = Irvinder | last2 = Jazdzyk | first2 = Mikael | last3 = Stein | first3 = Nathan N. | last4 = Prusevich | first4 = Polina | last5 = Miller | first5 = Glen P. | title = Design, Synthesis, and Characterization of a Persistent Nonacene Derivative | journal = J. Am. Chem. Soc. | year = 2010 | volume = 132 | issue = 4 | pages=1261–63 | doi = 10.1021/ja9095472}}.</ref>
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{| class="wikitable"
! Name
! [[Molecular formula|Molecular<br/>formula]]
! Number<br/>of rings
! [[Molar mass]]
! [[CAS registry number|CAS<br/>number]]
! [[Structural formula]]
|-
| [[Naphthalene]]
| C<sub>10</sub>H<sub>8</sub>
| align=center | 2
| 128.17 g mol<sup>−1</sup>
| 91-20-3
| [[File:Naphthalene-2D-Skeletal.svg|110px]]
|-
| [[Anthracene]]
| C<sub>14</sub>H<sub>10</sub>
| align=center | 3
| 178.23 g mol<sup>−1</sup>
| 120-12-7
| [[File:Anthracene-2D-Skeletal.png|160px]]
|-
| [[Tetracene]]
| C<sub>18</sub>H<sub>12</sub>
| align=center | 4
| 228.29 g mol<sup>−1</sup>
| 92-24-0
| [[File:Naftacene.svg|220px]]
|-
| [[Pentacene]]
| C<sub>22</sub>H<sub>14</sub>
| align=center | 5
| 278.35 g mol<sup>−1</sup>
| 135-48-8
| [[File:Pentacene.svg|270px]]
|-
| [[Hexacene]]
| C<sub>26</sub>H<sub>16</sub>
| align=center | 6
| 328.41 g mol<sup>−1</sup>
| 258-31-1
| [[File:Hexacene.svg|310px]]
|-
| [[Heptacene]]
| C<sub>30</sub>H<sub>18</sub>
| align=center | 7
| 378.46 g mol<sup>−1</sup>
| 258-38-8
| [[File:Heptaceen.png|360px]]
|-
| [[Octacene]]
| C<sub>34</sub>H<sub>20</sub>
| align=center | 8
| 428.52 g mol<sup>−1</sup>
| 258-33-3
|
|-
| [[Nonacene]]
| C<sub>38</sub>H<sub>22</sub>
| align=center | 9
| 478.58 g mol<sup>−1</sup>
| 
|
|-
|}

==Nomenclature==
[[Napthalene]] and [[anthracene]] have [[retained name]]s.<ref>{{BlueBook1993|page=164|url=http://www.acdlabs.com/iupac/nomenclature/93/r93_687.htm}}.</ref> Other acenes are named by a [[numerical prefix]] followed by the suffix "-acene", although [[tetracene]] also has the [[trivial name]] "[[naphthacene]]".<ref>{{BlueBook1979|rule=A-21|url=http://www.acdlabs.com/iupac/nomenclature/79/r79_63.htm}}.</ref>

==Related compounds==
A related group of compounds with 1,2-fused rings and with helical not linear structures are the [[helicene]]s. [[Polyquinane]]s and quinenes are fused cyclopentane rings.

==References==
{{reflist|2}}

[[Category:Acenes| ]]
[[Category:Functional classes]]

{{Imported from Wikipedia|title=Acene|id=368345846}}