Difference between revisions of "Acene"

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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 | pages = 452}}.</ref>
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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>
  
 
==Larger acenes==
 
==Larger acenes==
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Due to their increased [[Conjugated system|conjugation]] length the larger acenes are also studied <ref>{{cite journal|doi=10.1002/anie.200906002|title=Heptacene and Beyond: the Longest Characterized Acenes|year=2010|last1=Zade|first1=Sanjio S.|last2=Bendikov|first2=Michael|journal=Angewandte Chemie International Edition|pages=n/a}}</ref>. They are also building blocks for [[Carbon nanotube|nanotubes]] and [[graphene]].  Unsubstituted '''octacene''' (n=8) and '''nonacene''' (n=9) <ref>{{cite journal|doi=10.1002/anie.200906355|title=Photogeneration of Octacene and Nonacene|year=2010|last1=Tönshoff|first1=Christina|last2=Bettinger|first2=Holger F.|journal=Angewandte Chemie International Edition|pages=n/a}}</ref> have been detected in matrix isolation. A stable substituted nonacene was has also been reported <ref>{{cite journal|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|pages=1261}}</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.
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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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{{reflist|2}}
 
{{reflist|2}}
  
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[[Category:Acenes| ]]
 
[[Category:Conductive polymers]]
 
[[Category:Conductive polymers]]
 
[[Category:Organic semiconductors]]
 
[[Category:Organic semiconductors]]
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[[Category:Acenes]]
 
  
 
{{Imported from Wikipedia|title = Acene|id=368345846}}
 
{{Imported from Wikipedia|title = Acene|id=368345846}}

Revision as of 15:10, 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. Pentacene has been incorporated into organic field-effect transistors, 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.

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

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.[2]

Larger acenes

Due to their increased conjugation length the larger acenes are also studied [3]. They are also building blocks for nanotubes and graphene. Unsubstituted octacene (n=8) and nonacene (n=9) [4] have been detected in matrix isolation. A stable substituted nonacene was has also been reported [5]. 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

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. ↑ Zade, Sanjio S.; Bendikov, Michael Heptacene and Beyond: the Longest Characterized Acenes. Angewandte Chemie International Edition 2010, 49 (24), 1012–15. DOI: 10.1002/anie.200906002.
  4. ↑ Tönshoff, Christina; Bettinger, Holger F. Photogeneration of Octacene and Nonacene. Angewandte Chemie International Edition 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. Journal of the American Chemical Society 2010, 132 (4), 1261–63. DOI: 10.1021/ja9095472.
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