Acene

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File:Acenes general structure.svg
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 (Page Module:Chem2/styles.css has no content.C6H6) rings which have been linearly fused.[1][2] They follow the general molecular formula Page Module:Chem2/styles.css has no content.C4n+2H2n+4.

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:

Name Number of rings Molecular formula Structural formula
Naphthalene 2 Page Module:Chem2/styles.css has no content.C10H8 File:Naphthalene 200.svg
Anthracene 3 Page Module:Chem2/styles.css has no content.C14H10 File:Anthracene 200.svg
Tetracene 4 Page Module:Chem2/styles.css has no content.C18H12 File:Tetracene 200.svg
Pentacene 5 Page Module:Chem2/styles.css has no content.C22H14 File:Pentacene 200.svg
Hexacene 6 Page Module:Chem2/styles.css has no content.C26H16 File:Hexacene 200.svg
Heptacene 7 Page Module:Chem2/styles.css has no content.C30H18 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.[3]

Larger acenes

Due to their increased conjugation length the larger acenes are also studied.[4] Theoretically, a number of reports are available on longer chains using density functional methods.[5][6] They are also building blocks for nanotubes and graphene. Unsubstituted octacene (n=8) and nonacene (n=9)[7] have been detected in matrix isolation. The first reports of stable nonacene derivatives claimed that due to the electronic effects of the thioaryl substituents the compound is not a diradical but a closed-shell compound with the lowest HOMO–LUMO gap reported for any acene,[8] an observation in violation of Kasha's rule. Subsequent work by others on different derivatives included crystal structures, with no such violations.[9] The on-surface synthesis and characterization of unsubstituted, parent nonacene (n=9)[10] and decacene (n=10)[11] have been reported. In 2020, scientists reported about the creation of dodecacene (n=12)[12] 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.[13]

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.

Benz[a]anthracene, an isomer of tetracene, has three rings connected in a line and one ring connected at an angle.

References

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  1. ^ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "acenes". Script error: No such module "CS1 identifiers".
  2. ^ Electronic structure of higher acenes and polyacene: The perspective developed by theoretical analyses Holger F. Bettinger Pure Appl. Chem., Vol. 82, No. 4, pp. 905–915, 2010. Script error: No such module "CS1 identifiers".
  3. ^ Page Module:Citation/CS1/styles.css has no content.Anthony, John E. (2008). "The Larger Acenes: Versatile Organic Semiconductors". Angewandte Chemie International Edition. 47 (3): 452–83. Bibcode:2008ACIE...47..452A. doi:10.1002/anie.200604045. PMID 18046697.
  4. ^ Page Module:Citation/CS1/styles.css has no content.Zade, Sanjio S.; Bendikov, Michael (2010). "Heptacene and Beyond: the Longest Characterized Acenes". Angewandte Chemie International Edition. 49 (24): 4012–5. Bibcode:2010ACIE...49.4012Z. doi:10.1002/anie.200906002. PMID 20468014.
  5. ^ Page Module:Citation/CS1/styles.css has no content.Wu, Chun-Shian; Chai, Jeng-Da (2015-05-12). "Electronic Properties of Zigzag Graphene Nanoribbons Studied by TAO-DFT". Journal of Chemical Theory and Computation. 11 (5): 2003–2011. Bibcode:2015JCTC...11.2003W. doi:10.1021/ct500999m. ISSN 1549-9618. PMID 26894252.
  6. ^ Page Module:Citation/CS1/styles.css has no content.Seenithurai, Sonai; Chai, Jeng-Da (2016-09-09). "Effect of Li Adsorption on the Electronic and Hydrogen Storage Properties of Acenes: A Dispersion-Corrected TAO-DFT Study". Scientific Reports. 6 (1) 33081. arXiv:1606.03489. Bibcode:2016NatSR...633081S. doi:10.1038/srep33081. ISSN 2045-2322. PMC 5016802. PMID 27609626.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Tönshoff, Christina; Bettinger, Holger F. (2010). "Photogeneration of Octacene and Nonacene". Angewandte Chemie International Edition. 49 (24): 4125–8. Bibcode:2010ACIE...49.4125T. doi:10.1002/anie.200906355. PMID 20432492.
  8. ^ Page Module:Citation/CS1/styles.css has no content.Kaur, Irvinder; Jazdzyk, Mikael; Stein, Nathan N.; Prusevich, Polina; Miller, Glen P. (2010). "Design, Synthesis, and Characterization of a Persistent Nonacene Derivative". Journal of the American Chemical Society. 132 (4): 1261–3. Bibcode:2010JAChS.132.1261K. doi:10.1021/ja9095472. PMID 20055388.
  9. ^ Page Module:Citation/CS1/styles.css has no content.Purushothaman, Balaji; Bruzek, Matthew; Parkin, Sean; Miller, Anne-Frances; Anthony, John (2011). "Synthesis and Structural Characterization of Crystalline Nonacenes". Angew. Chem. Int. Ed. Engl. 50 (31): 7013–7017. Bibcode:2011ACIE...50.7013P. doi:10.1002/anie.201102671. PMID 21717552.
  10. ^ 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 Script error: No such module "CS1 identifiers".
  11. ^ 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. Script error: No such module "CS1 identifiers".
  12. ^ Page Module:Citation/CS1/styles.css has no content.Eisenhut, Frank; Kühne, Tim; García, Fátima; Fernández, Saleta; Guitián, Enrique; Pérez, Dolores; Trinquier, Georges; Cuniberti, Gianaurelio; Joachim, Christian; Peña, Diego; Moresco, Francesca (2020-01-28). "Dodecacene Generated on Surface: Reopening of the Energy Gap". ACS Nano. 14 (1): 1011–1017. arXiv:2004.02517. Bibcode:2020ACSNa..14.1011E. doi:10.1021/acsnano.9b08456. ISSN 1936-0851. PMID 31829618. S2CID 209341741.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Ruan, Zilin; Schramm, Jakob; Bauer, John B.; Naumann, Tim; Bettinger, Holger F.; Tonner-Zech, Ralf; Gottfried, J. Michael (2024-01-12). "Synthesis of Tridecacene by Multistep Single-Molecule Manipulation". Journal of the American Chemical Society. 146 (6): 3700–3709. Bibcode:2024JAChS.146.3700R. doi:10.1021/jacs.3c09392. ISSN 0002-7863. PMC 10870776. PMID 38216144.

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