Difference between revisions of "Acene"
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[[Image:Acenes general structure.svg|thumb|The general structural formula for acenes]] | [[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 5 | + | '''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> |
{{clear}} | {{clear}} | ||
{| class="wikitable" | {| class="wikitable" | ||
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| C<sub>10</sub>H<sub>8</sub> | | C<sub>10</sub>H<sub>8</sub> | ||
| align=center | 2 | | align=center | 2 | ||
| − | | 128.17 | + | | 128.17 g mol<sup>−1</sup> |
| 91-20-3 | | 91-20-3 | ||
| [[File:Naphthalene-2D-Skeletal.svg|110px]] | | [[File:Naphthalene-2D-Skeletal.svg|110px]] | ||
| Line 21: | Line 21: | ||
| C<sub>14</sub>H<sub>10</sub> | | C<sub>14</sub>H<sub>10</sub> | ||
| align=center | 3 | | align=center | 3 | ||
| − | | 178.23 | + | | 178.23 g mol<sup>−1</sup> |
| 120-12-7 | | 120-12-7 | ||
| [[File:Anthracene-2D-Skeletal.png|160px]] | | [[File:Anthracene-2D-Skeletal.png|160px]] | ||
| Line 28: | Line 28: | ||
| C<sub>18</sub>H<sub>12</sub> | | C<sub>18</sub>H<sub>12</sub> | ||
| align=center | 4 | | align=center | 4 | ||
| − | | 228.29 | + | | 228.29 g mol<sup>−1</sup> |
| 92-24-0 | | 92-24-0 | ||
| [[File:Naftacene.svg|220px]] | | [[File:Naftacene.svg|220px]] | ||
| Line 35: | Line 35: | ||
| C<sub>22</sub>H<sub>14</sub> | | C<sub>22</sub>H<sub>14</sub> | ||
| align=center | 5 | | align=center | 5 | ||
| − | | 278.35 | + | | 278.35 g mol<sup>−1</sup> |
| 135-48-8 | | 135-48-8 | ||
| [[File:Pentacene.svg|270px]] | | [[File:Pentacene.svg|270px]] | ||
| Line 42: | Line 42: | ||
| C<sub>26</sub>H<sub>16</sub> | | C<sub>26</sub>H<sub>16</sub> | ||
| align=center | 6 | | align=center | 6 | ||
| − | | 328.41 | + | | 328.41 g mol<sup>−1</sup> |
| 258-31-1 | | 258-31-1 | ||
| [[File:Hexacene.svg|310px]] | | [[File:Hexacene.svg|310px]] | ||
| Line 49: | Line 49: | ||
| C<sub>30</sub>H<sub>18</sub> | | C<sub>30</sub>H<sub>18</sub> | ||
| align=center | 7 | | align=center | 7 | ||
| − | | 378.46 | + | | 378.46 g mol<sup>−1</sup> |
| | | | ||
| [[File:Heptaceen.png|360px]] | | [[File:Heptaceen.png|360px]] | ||
| Line 65: | Line 65: | ||
[[Category:Organic semiconductors]] | [[Category:Organic semiconductors]] | ||
| − | {{Imported from Wikipedia|title = Acene|id=368345846}} | + | {{Imported from Wikipedia|title=Acene|id=368345846}} |
Revision as of 14:33, 28 June 2010
Acenes (sometimes referred to as polyacenes) form a functional class of organic compounds: they are polycyclic aromatic hydrocarbons made up of linearly fused benzene rings.[1] The larger acenes have potential interest in optoelectronic applications and as organic semiconductors.[2][3] Pentacene has been incorporated into organic field-effect transistors, reaching charge carrier mobilities as high as 5 cm2 V−1 s−1.[2] Unsubstituted acenes larger than pentacene have only been studied by matrix isolation techniques,[2][3][4] although substituted acenes up to nonacene have been isolated.[2][5]
| Name | Molecular formula |
Number of rings |
Molar mass | CAS number |
Structural formula |
|---|---|---|---|---|---|
| Naphthalene | C10H8 | 2 | 128.17 g mol−1 | 91-20-3 | 
|
| Anthracene | C14H10 | 3 | 178.23 g mol−1 | 120-12-7 | 
|
| Tetracene | C18H12 | 4 | 228.29 g mol−1 | 92-24-0 | 220px |
| Pentacene | C22H14 | 5 | 278.35 g mol−1 | 135-48-8 | 
|
| Hexacene | C26H16 | 6 | 328.41 g mol−1 | 258-31-1 | 
|
| Heptacene | C30H18 | 7 | 378.46 g mol−1 | 
|
Related compounds
A related group of compounds with 1,2-fused rings and with helical not linear structures are the helicenes. Polyquinanes and quinenes are fused cyclopentane rings.
References
- ↑ Glossary of class names of organic compounds and reactivity intermediates based on structure (IUPAC Recommendations 1995). Pure Appl. Chem. 1995, 67 (8-9), 1307–75 at 1310. DOI: 10.1351/pac199567081307.
- ↑ 2.0 2.1 2.2 2.3 Anthony, John E. The Larger Acenes: Versatile Organic Semiconductors. Angew. Chem., Int. Ed. Engl. 2008, 47 (3), 452–83. DOI: 10.1002/anie.200604045.
- ↑ 3.0 3.1 Zade, Sanjio S.; Bendikov, Michael Heptacene and Beyond: the Longest Characterized Acenes. Angew. Chem., Int. Ed. Engl. 2010, 49 (24), 1012–15. DOI: 10.1002/anie.200906002.
- ↑ Tönshoff, Christina; Bettinger, Holger F. Photogeneration of Octacene and Nonacene. Angew. Chem. Int. Ed. Engl. 2010, 49 (24), 4125–28. DOI: 10.1002/anie.200906355.
- ↑ Kaur, Irvinder; Jazdzyk, Mikael; Stein, Nathan N.; Prusevich, Polina; Miller, Glen P. Design, Synthesis, and Characterization of a Persistent Nonacene Derivative. J. Am. Chem. Soc. 2010, 132 (4), 1261–63. DOI: 10.1021/ja9095472.
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This page was originally imported from Wikipedia, specifically this version of the article "Acene". Please see the history page on Wikipedia for the original authors. This WikiChem article may have been modified since it was imported. It is licensed under the Creative Commons Attribution–Share Alike 3.0 Unported license. |
