Acene
Class of chemical compounds
title: "Acene" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["acenes", "conductive-polymers", "organic-semiconductors", "polycyclic-aromatic-hydrocarbons"] description: "Class of chemical compounds" topic_path: "science/chemistry" source: "https://en.wikipedia.org/wiki/Acene" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
::summary Class of chemical compounds ::
::figure[src="https://upload.wikimedia.org/wikipedia/commons/5/59/Acenes_general_structure.svg" caption="The general structural formula for acenes"] ::
In organic chemistry, the acenes or polyacenes are a class of organic compounds and polycyclic aromatic hydrocarbons made up of benzene () rings which have been linearly fused. They follow the general molecular formula .
The larger representatives have potential interest in optoelectronic applications and are actively researched in chemistry and electrical engineering. Pentacene has been incorporated into organic field-effect transistors, reaching charge carrier mobilities as high as 5 cm2/Vs.
The first unsubstituted members are listed in the following table: ::data[format=table]
| Name | Number of rings | Molecular formula | Structural formula |
|---|---|---|---|
| Naphthalene | 2 | [[File:Naphthalene 200.svg | |
| Anthracene | 3 | [[File:Anthracene 200.svg | |
| Tetracene | 4 | [[File:Tetracene 200.svg | |
| Pentacene | 5 | [[File:Pentacene 200.svg | |
| Hexacene | 6 | [[File:Hexacene 200.svg | |
| Heptacene | 7 | [[File:Heptacene 200.svg | |
| :: |
Hexacene is not stable in air, and dimerises upon isolation. Heptacene (and larger acenes) is very reactive and has only been isolated in a matrix. However, bis(trialkylsilylethynylated) versions of heptacene have been isolated as crystalline solids.
Larger acenes
Due to their increased conjugation length the larger acenes are also studied. for the first time. Four years later, in the beginning of 2024, Ruan et al. succeeded in synthesizing unsubstituted tridecacene (n=13) on a (111)-gold surface. The acene was characterized by STM- and STS-measurements.
Related compounds
The acene series have the consecutive rings linked in a linear chain, but other chain linkages are possible. The phenacenes have a zig-zag structure and the helicenes have a helical structure. File:Heptacene 200.svg|Heptacene File:7-phenacene.svg|[7]Phenacene File:M-heptahelicene.svg|M-heptahelicene
Benz[a]anthracene, an isomer of tetracene, has three rings connected in a line and one ring connected at an angle.
References
References
- (2020-01-28). "Dodecacene Generated on Surface: Reopening of the Energy Gap". ACS Nano.
- (2024-01-12). "Synthesis of Tridecacene by Multistep Single-Molecule Manipulation". Journal of the American Chemical Society.
- "acenes".
- (2008). "The Larger Acenes: Versatile Organic Semiconductors". Angewandte Chemie International Edition.
- (2010). "Heptacene and Beyond: the Longest Characterized Acenes". Angewandte Chemie International Edition.
- (2015-05-12). "Electronic Properties of Zigzag Graphene Nanoribbons Studied by TAO-DFT". Journal of Chemical Theory and Computation.
- (2016-09-09). "Effect of Li Adsorption on the Electronic and Hydrogen Storage Properties of Acenes: A Dispersion-Corrected TAO-DFT Study". Scientific Reports.
- (2010). "Photogeneration of Octacene and Nonacene". Angewandte Chemie International Edition.
- (2010). "Design, Synthesis, and Characterization of a Persistent Nonacene Derivative". Journal of the American Chemical Society.
- (2011). "Synthesis and Structural Characterization of Crystalline Nonacenes". Angew. Chem. Int. Ed. Engl..
- ''Nonacene Generated by On-Surface Dehydrogenation'' Rafal Zuzak, Ruth Dorel, Mariusz Krawiec, Bartosz Such, Marek Kolmer, Marek Szymonski, Antonio M. Echavarren, Szymon Godlewski, ACS Nano, 2017, 11 (9), pp 9321–9329 {{doi. 10.1021/acsnano.7b04728
- ''Decacene: On-Surface Generation'' J. Krüger, F. García, F. Eisenhut, D. Skidin, J. M. Alonso, E. Guitián, D. Pérez, G. Cuniberti, F. Moresco, D. Peña, Angew. Chem. Int. Ed. 2017, 56, 11945. {{doi. 10.1002/anie.201706156
::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::