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" | ||
! Name | ! Name | ||
| − | ! [[Molecular formula]] | + | ! [[Molecular formula|Molecular<br/>formula]] |
! Number<br/>of rings | ! Number<br/>of rings | ||
! [[Molar mass]] | ! [[Molar mass]] | ||
| − | ! [[CAS number]] | + | ! [[CAS registry number|CAS<br/>number]] |
! [[Structural formula]] | ! [[Structural formula]] | ||
|- | |- | ||
| Line 14: | Line 14: | ||
| 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> |
| + | | 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== | ==Related compounds== | ||
| Line 62: | Line 79: | ||
[[Category:Acenes| ]] | [[Category:Acenes| ]] | ||
| − | [[Category: | + | [[Category:Functional classes]] |
| − | |||
| − | {{Imported from Wikipedia|title = Acene|id=368345846}} | + | {{Imported from Wikipedia|title=Acene|id=368345846}} |
Latest revision as of 19:04, 2 July 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 | 258-38-8 | 
|
| Octacene | C34H20 | 8 | 428.52 g mol−1 | 258-33-3 | |
| Nonacene | C38H22 | 9 | 478.58 g mol−1 |
Nomenclature
Napthalene and anthracene have retained names.[6] Other acenes are named by a numerical prefix followed by the suffix "-acene", although tetracene also has the trivial name "naphthacene".[7]
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.
- ↑ A Guide to IUPAC Nomenclature of Organic Compounds; IUPAC Recommendations 1993; Blackwell Science: Oxford, 1993; p 164. ISBN 0-632-03488-2, <http://www.acdlabs.com/iupac/nomenclature/93/r93_687.htm>.
- ↑ Rule A-21. In Nomenclature of Organic Chemistry, Sections A, B, C, D, E, F, and H; IUPAC Recommendations 1979; Pergamon: Oxford, 1979. ISBN 0-08022-369-9, <http://www.acdlabs.com/iupac/nomenclature/79/r79_63.htm>.
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