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.<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 cm2/Vs.<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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'''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 cm2/Vs.<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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Revision as of 14:24, 28 June 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/Vs.[4] Unsubstituted acenes larger than pentacene have only been studied by matrix isolation techniques,[4][3][5] although substituted acenes up to nonacene have been isolated.[4][6]

Naam Molecular formula Number of rings Molar mass CAS number Structural formula
Naphthalene C10H8 2 128.17 g/mol 91-20-3 Naphthalene-2D-Skeletal.svg
Anthracene C14H10 3 178.23 g/mol 120-12-7 Anthracene-2D-Skeletal.png
Tetracene C18H12 4 228.29 g/mol 92-24-0 220px
Pentacene C22H14 5 278.35 g/mol 135-48-8 Pentacene.svg
Hexacene C26H16 6 328.41 g/mol 258-31-1 Hexacene.svg
Heptacene C30H18 7 378.46 g/mol Heptaceen.png

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. ↑ 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. ↑ 4.0 4.1 4.2 Cite error: Invalid <ref> tag; no text was provided for refs named Antony"
  5. ↑ 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.
  6. ↑ 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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