Nonacene

Nonacene
Skeletal formula of nonacene
Skeletal formula of nonacene
Names
Preferred IUPAC name
Nonacene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C38H22/c1-2-6-24-10-28-14-32-18-36-22-38-20-34-16-30-12-26-8-4-3-7-25(26)11-29(30)15-33(34)19-37(38)21-35(36)17-31(32)13-27(28)9-23(24)5-1/h1-22H
    Key: UIFXPOUSHBMMEG-UHFFFAOYSA-N
  • C1=CC=C2C=C3C=C4C=C5C=C6C=C7C=C8C=C9C=CC=CC9=CC8=CC7=CC6=CC5=CC4=CC3=CC2=C1
Properties
C38H22
Molar mass 478.594 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Nonacene is an organic compound and a polycyclic aromatic hydrocarbon and the ninth member of the acene or polyacene family of linear fused benzene rings. Its chemical formula is C38H22.[1]

Structure

Like other acenes, nonacene features a planar, rectilinear arrangement of nine fused benzene rings.[2] This extended π-conjugated system gives rise to its characteristic electronic properties.

As the number of fused benzene rings increases, the energy gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) decreases. For nonacene, this gap is significantly smaller than that of smaller acenes such as pentacene (five rings) or tetracene (four rings), positioning it as a potential low-bandgap semiconductor.[3]

Synthesis

In 2010, the Bettinger group reported a photochemical synthesis of octacene and nonacene, utilizing a cryogenic matrix-isolation technique to stabilize these highly reactive acenes. This approach requires precursors containing a double α-diketone bridge to enable the formation of octacene and nonacene.[4][5]

Uses

Nonacene is of significant interest in organic electronics due to its exceptional semiconductor properties, though its high chemical reactivity and instability have historically made it one of the most challenging acenes to synthesize and isolate.[6][7]

References

  1. ^ "Nonacene". NIST. Retrieved 30 March 2026.
  2. ^ "ZFIN ChEBI: nonacene". zfin.org. Retrieved 30 March 2026.
  3. ^ Zuzak, Rafal; Dorel, Ruth; Krawiec, Mariusz; Such, Bartosz; Kolmer, Marek; Szymonski, Marek; Echavarren, Antonio M.; Godlewski, Szymon (26 September 2017). "Nonacene Generated by On-Surface Dehydrogenation". ACS Nano. 11 (9): 9321–9329. Bibcode:2017ACSNa..11.9321Z. doi:10.1021/acsnano.7b04728. PMID 28817255.
  4. ^ Lerena, Laura; Zuzak, Rafal; Godlewski, Szymon; Echavarren, Antonio M. (2024). "The Journey for the Synthesis of Large Acenes". Chemistry – A European Journal. 30 (57) e202402122. Bibcode:2024ChEuJ..30E2122L. doi:10.1002/chem.202402122. ISSN 1521-3765. PMID 39077888.
  5. ^ Kaur, Irvinder; Jazdzyk, Mikael; Stein, Nathan N.; Prusevich, Polina; Miller, Glen P. (3 February 2010). "Design, Synthesis, and Characterization of a Persistent Nonacene Derivative". Journal of the American Chemical Society. 132 (4): 1261–1263. Bibcode:2010JAChS.132.1261K. doi:10.1021/ja9095472. PMID 20055388. Retrieved 30 March 2026.
  6. ^ "Preparative-scale synthesis of nonacene – CEMES". cemes.fr. Retrieved 30 March 2026.
  7. ^ "UNH chemists create molecule with promising semiconductor properties". chemeurope.com. Retrieved 30 March 2026.

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