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]]
  
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'''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. [[Pentacene]] has been incorporated into [[organic field-effect transistor]]s, reaching charge carrier mobilities as high as 5 cm2/Vs. Unsubstituted acenes larger than pentacene have only been studied by [[matrix isolation]] techniques, although substituted acenes up to nonacene have been isolated.
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'''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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{{clear}}
 
{| class="wikitable"
 
{| class="wikitable"
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! Naam
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! Name
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! [[Molecular formula]]
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! [[Molecular formula|Molecular<br/>formula]]
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! Number of rings
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! Number<br/>of rings
 
! [[Molar mass]]
 
! [[Molar mass]]
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! [[CAS number]]
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! [[CAS registry number|CAS<br/>number]]
 
! [[Structural formula]]
 
! [[Structural formula]]
 
|-
 
|-
 
| [[Naphthalene]]
 
| [[Naphthalene]]
 
| C<sub>10</sub>H<sub>8</sub>
 
| C<sub>10</sub>H<sub>8</sub>
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| 2
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| align=center | 2
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| 128.17 g/[[Mole (unit)|mol]]
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| 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]]
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| [[Anthracene]]
 
| [[Anthracene]]
 
| C<sub>14</sub>H<sub>10</sub>
 
| C<sub>14</sub>H<sub>10</sub>
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| 3
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| align=center | 3
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| 178.23 g/[[Mole (unit)|mol]]
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| 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]]
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| [[Tetracene]]
 
| [[Tetracene]]
 
| C<sub>18</sub>H<sub>12</sub>
 
| C<sub>18</sub>H<sub>12</sub>
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| 4
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| align=center | 4
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| 228.29 g/[[Mole (unit)|mol]]
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| 228.29 g mol<sup>−1</sup>
 
| 92-24-0
 
| 92-24-0
 
| [[File:Naftacene.svg|220px]]
 
| [[File:Naftacene.svg|220px]]
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| [[Pentacene]]
 
| [[Pentacene]]
 
| C<sub>22</sub>H<sub>14</sub>
 
| C<sub>22</sub>H<sub>14</sub>
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| 5
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| align=center | 5
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| 278.35 g/[[Mole (unit)|mol]]
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| 278.35 g mol<sup>−1</sup>
 
| 135-48-8
 
| 135-48-8
 
| [[File:Pentacene.svg|270px]]
 
| [[File:Pentacene.svg|270px]]
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| [[Hexacene]]
 
| [[Hexacene]]
 
| C<sub>26</sub>H<sub>16</sub>
 
| C<sub>26</sub>H<sub>16</sub>
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| 6
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| align=center | 6
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| 328.41 g/[[Mole (unit)|mol]]
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| 328.41 g mol<sup>−1</sup>
 
| 258-31-1
 
| 258-31-1
 
| [[File:Hexacene.svg|310px]]
 
| [[File:Hexacene.svg|310px]]
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| [[Heptacene]]
 
| [[Heptacene]]
 
| C<sub>30</sub>H<sub>18</sub>
 
| C<sub>30</sub>H<sub>18</sub>
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| 7
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| align=center | 7
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| 378.46 g/[[Mole (unit)|mol]]
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| 378.46 g mol<sup>−1</sup>
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| 258-38-8
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| [[File:Heptaceen.png|360px]]
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|-
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| [[Octacene]]
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| C<sub>34</sub>H<sub>20</sub>
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| align=center | 8
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| 428.52 g mol<sup>−1</sup>
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| 258-33-3
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|
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|-
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| [[Nonacene]]
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| C<sub>38</sub>H<sub>22</sub>
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| align=center | 9
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| 478.58 g mol<sup>−1</sup>
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|
 
|
 
|
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| [[File:Heptaceen.png|360px]]
 
 
|-
 
|-
 
|}
 
|}
  
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The last members, [[hexacene]] and [[heptacene]], are very reactive and have only been isolated in a matrix.  However, bis(trialkylsilylethynylated) versions of hexacene and heptacene have been isolated as crystalline solids.<ref>{{citation | doi = 10.1002/anie.200604045 | title = The Larger Acenes: Versatile Organic Semiconductors | year = 2008 | last1 = Anthony | first1 = John  E. | journal = Angew. Chem., Int. Ed. Engl. | volume = 47 | issue = 3 | pages = 452–83}}.</ref>
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==Nomenclature==
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[[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>
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==Larger acenes==
 
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Due to their increased [[Conjugated system|conjugation]] length the larger acenes are also studied <ref>{{citation |doi=10.1002/anie.200906002|title=Heptacene and Beyond: the Longest Characterized Acenes|year=2010| volume = 49 | issue = 24 | last1=Zade|first1=Sanjio S.|last2=Bendikov|first2=Michael|journal=Angewandte Chemie International Edition|pages=1012–15}}.</ref>. They are also building blocks for [[Carbon nanotube|nanotubes]] and [[graphene]]. Unsubstituted '''octacene''' (n=8) and '''nonacene''' (n=9) <ref>{{citation |doi=10.1002/anie.200906355|title=Photogeneration of Octacene and Nonacene|year=2010| volume = 49 | issue = 24 | last1=Tönshoff|first1=Christina|last2=Bettinger|first2=Holger F.|journal=Angewandte Chemie International Edition|pages=4125–28}}.</ref> have been detected in matrix isolation. A stable substituted nonacene was has also been reported <ref>{{citation |doi=10.1021/ja9095472|title=Design, Synthesis, and Characterization of a Persistent Nonacene Derivative|year=2010|last1=Kaur|first1=Irvinder|last2=Jazdzyk|first2=Mikael|last3=Stein|first3=Nathan N.|last4=Prusevich|first4=Polina|last5=Miller|first5=Glen P.|journal=Journal of the American Chemical Society|volume=132| issue = 4 | pages=1261–63}}.</ref>. Due to its array of substituents the compound is not a [[diradical]] but a closed-shell compound with the lowest HOMO-LUMO gap reported for any acene.
 
  
 
==Related compounds==
 
==Related compounds==
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[[Category:Acenes| ]]
 
[[Category:Acenes| ]]
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[[Category:Conductive polymers]]
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[[Category:Functional classes]]
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[[Category:Organic semiconductors]]
 
  
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{{Imported from Wikipedia|title = Acene|id=368345846}}
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{{Imported from Wikipedia|title=Acene|id=368345846}}

Latest revision as of 19:04, 2 July 2010

The general structural formula for acenes

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 Naphthalene-2D-Skeletal.svg
Anthracene C14H10 3 178.23 g mol−1 120-12-7 Anthracene-2D-Skeletal.png
Tetracene C18H12 4 228.29 g mol−1 92-24-0 220px
Pentacene C22H14 5 278.35 g mol−1 135-48-8 Pentacene.svg
Hexacene C26H16 6 328.41 g mol−1 258-31-1 Hexacene.svg
Heptacene C30H18 7 378.46 g mol−1 258-38-8 Heptaceen.png
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

  1. ↑ 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. ↑ 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. ↑ 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ 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>.
  7. ↑ 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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