Difference between revisions of "Acene"
Physchim62 (talk | contribs) (Created page with 'thumb|The general structural formula for acenes '''Acenes''' or '''polyacenes''' is a class of organic compounds and [[polycyclic arom…') |
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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''' | + | '''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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{| class="wikitable" | {| class="wikitable" | ||
! Naam | ! Naam | ||
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! [[Structural formula]] | ! [[Structural formula]] | ||
|- | |- | ||
| − | | [[ | + | | [[Naphthalene]] |
| C<sub>10</sub>H<sub>8</sub> | | C<sub>10</sub>H<sub>8</sub> | ||
| 2 | | 2 | ||
| − | | 128 | + | | 128.17 g/[[Mole (unit)|mol]] |
| 91-20-3 | | 91-20-3 | ||
| [[File:Naphthalene-2D-Skeletal.svg|110px]] | | [[File:Naphthalene-2D-Skeletal.svg|110px]] | ||
| Line 23: | Line 21: | ||
| C<sub>14</sub>H<sub>10</sub> | | C<sub>14</sub>H<sub>10</sub> | ||
| 3 | | 3 | ||
| − | | 178 | + | | 178.23 g/[[Mole (unit)|mol]] |
| 120-12-7 | | 120-12-7 | ||
| [[File:Anthracene-2D-Skeletal.png|160px]] | | [[File:Anthracene-2D-Skeletal.png|160px]] | ||
| Line 30: | Line 28: | ||
| C<sub>18</sub>H<sub>12</sub> | | C<sub>18</sub>H<sub>12</sub> | ||
| 4 | | 4 | ||
| − | | 228 | + | | 228.29 g/[[Mole (unit)|mol]] |
| 92-24-0 | | 92-24-0 | ||
| [[File:Naftacene.svg|220px]] | | [[File:Naftacene.svg|220px]] | ||
| Line 37: | Line 35: | ||
| C<sub>22</sub>H<sub>14</sub> | | C<sub>22</sub>H<sub>14</sub> | ||
| 5 | | 5 | ||
| − | | 278 | + | | 278.35 g/[[Mole (unit)|mol]] |
| 135-48-8 | | 135-48-8 | ||
| [[File:Pentacene.svg|270px]] | | [[File:Pentacene.svg|270px]] | ||
| Line 44: | Line 42: | ||
| C<sub>26</sub>H<sub>16</sub> | | C<sub>26</sub>H<sub>16</sub> | ||
| 6 | | 6 | ||
| − | | 328 | + | | 328.41 g/[[Mole (unit)|mol]] |
| 258-31-1 | | 258-31-1 | ||
| [[File:Hexacene.svg|310px]] | | [[File:Hexacene.svg|310px]] | ||
| Line 51: | Line 49: | ||
| C<sub>30</sub>H<sub>18</sub> | | C<sub>30</sub>H<sub>18</sub> | ||
| 7 | | 7 | ||
| − | | 378 | + | | 378.46 g/[[Mole (unit)|mol]] |
| | | | ||
| [[File:Heptaceen.png|360px]] | | [[File:Heptaceen.png|360px]] | ||
| + | |- | ||
|} | |} | ||
| − | 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>{{ | + | 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> |
==Larger acenes== | ==Larger acenes== | ||
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. | 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. | ||
| + | |||
==Related compounds== | ==Related compounds== | ||
A related group of compounds with 1,2-fused rings and with helical not linear structures are the [[helicene]]s. [[Polyquinane]]s and quinenes are fused cyclopentane rings. | A related group of compounds with 1,2-fused rings and with helical not linear structures are the [[helicene]]s. [[Polyquinane]]s and quinenes are fused cyclopentane rings. | ||
Revision as of 14:05, 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. 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 | 
|
| Anthracene | C14H10 | 3 | 178.23 g/mol | 120-12-7 | 
|
| Tetracene | C18H12 | 4 | 228.29 g/mol | 92-24-0 | 220px |
| Pentacene | C22H14 | 5 | 278.35 g/mol | 135-48-8 | 
|
| Hexacene | C26H16 | 6 | 328.41 g/mol | 258-31-1 | 
|
| Heptacene | C30H18 | 7 | 378.46 g/mol | 
|
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
- ↑ 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.
- ↑ Anthony, John E. The Larger Acenes: Versatile Organic Semiconductors. Angew. Chem., Int. Ed. Engl. 2008, 47, 452. DOI: 10.1002/anie.200604045.
- ↑ "Heptacene and Beyond: the Longest Characterized Acenes" (2010). Angewandte Chemie International Edition: n/a. doi:10.1002/anie.200906002.
- ↑ "Photogeneration of Octacene and Nonacene" (2010). Angewandte Chemie International Edition: n/a. doi:10.1002/anie.200906355.
- ↑ "Design, Synthesis, and Characterization of a Persistent Nonacene Derivative" (2010). Journal of the American Chemical Society 132: 1261. doi:10.1021/ja9095472.
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