Octacene

Octacene
	Skeletal formula of heptacene
Names
	Preferred IUPAC name Octacene
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:33165;
ChemSpider	4574182;
PubChem CID	5460708;
	InChI InChI=1S/C34H20/c1-2-6-22-10-26-14-30-18-34-20-32-16-28-12-24-8-4-3-7-23(24)11-27(28)15-31(32)19-33(34)17-29(30)13-25(26)9-21(22)5-1/h1-20H Key: PFTXKXWAXWAZBP-UHFFFAOYSA-N;
	SMILES C1=CC=C2C=C3C=C4C=C5C=C6C=C7C=C8C=CC=CC8=CC7=CC6=CC5=CC4=CC3=CC2=C1;
Properties
Chemical formula	C34H20
Molar mass	428.534 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Octacene is an organic compound and a polycyclic aromatic hydrocarbon and the eighth member of the acene or polyacene family of linear fused benzene rings.^[1]^[2]^[3] Its сhemical formula is C₃₄H₂₀.

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]

References

^ "Octacene". NIST. Retrieved 24 July 2025.
^ Siegel, Jay S.; Wu, Yao-Ting (13 November 2014). Polyarenes I. Springer. p. 21. ISBN 978-3-662-43379-9. Retrieved 24 July 2025.
^ Zeitter, Nico; Hippchen, Nikolai; Baur, Philipp; Unterreiner, Tamara V.; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F. (February 2024). "Pentacene to Octacene: The Limit of Fourfold TIPS-Ethynylation". Organic Materials. 06 (1): 12–17. doi:10.1055/a-2241-0243. ISSN 2625-1825. Retrieved 25 July 2025.
^ 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. Retrieved 24 July 2025.{{cite journal}}: CS1 maint: article number as page number (link)

[1] "Octacene". NIST. Retrieved 24 July 2025.

[2] Siegel, Jay S.; Wu, Yao-Ting (13 November 2014). Polyarenes I. Springer. p. 21. ISBN 978-3-662-43379-9. Retrieved 24 July 2025.

[3] Zeitter, Nico; Hippchen, Nikolai; Baur, Philipp; Unterreiner, Tamara V.; Rominger, Frank; Freudenberg, Jan; Bunz, Uwe H. F. (February 2024). "Pentacene to Octacene: The Limit of Fourfold TIPS-Ethynylation". Organic Materials. 06 (1): 12–17. doi:10.1055/a-2241-0243. ISSN 2625-1825. Retrieved 25 July 2025.

[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. Retrieved 24 July 2025.{{cite journal}}: CS1 maint: article number as page number (link)

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Octacene

Synthesis

References

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