Polyyne

A polyyne is any organic compound with alternating single and triple bonds; that is, a series of consecutive alkynes, (−C≡C−)_n with n greater than 1. These compounds are also called polyacetylenes, especially in the natural products and chemical ecology literature,^[1] even though this nomenclature more properly refers to acetylene polymers composed of alternating single and double bonds (−CR=CR′−)_n with n greater than 1. They are also sometimes referred to as oligoynes,^[2]^{[needs IPA]} or carbinoids after "carbyne" (−C≡C−)_∞, the hypothetical allotrope of carbon that would be the ultimate member of the series.^[3]^[4] The synthesis of this substance has been claimed several times since the 1960s, but those reports have been disputed.^[5] Indeed, the substances identified as short chains of "carbyne" in many early organic synthesis attempts^[6] would be called polyynes today.

The simplest polyyne is diacetylene or butadiyne, H−C≡C−C≡C−H. Along with cumulenes, polyynes are distinguished from other organic chains by their rigidity and high conductivity,^[7] both of which make them promising as wires in molecular nanotechnology. Polyynes have been detected in interstellar molecular clouds where hydrogen is scarce.^{[citation needed]}

^ Cite error: The named reference Blacklock2008 was invoked but never defined (see the help page).
^ Gibtner, Thomas; Hampel, Frank; Gisselbrecht, Jean-Paul; Hirsch, Andreas (2002). "End-cap stabilized oligoynes: Model compounds for the linear sp carbon allotrope carbyne". Chemistry: A European Journal. 8 (2): 408–432. doi:10.1002/1521-3765(20020118)8:2<408::AID-CHEM408>3.0.CO;2-L. PMID 11843154.
^ Heimann, R.B.; Evsyukov, S.E.; Kavan, L., eds. (1999). Carbyne and carbynoid structures. Physics and Chemistry of Materials with Low-Dimensional Structures. Vol. 21. p. 452. ISBN 978-0-7923-5323-2.
^ Chalifoux, Wesley A.; Tykwinski, Rik R. (2009). "Synthesis of extended polyynes: Toward carbyne". Comptes Rendus Chimie. 12 (3–4): 341–358. doi:10.1016/j.crci.2008.10.004. In Avancés récentes en chimie des acétylènes – Recent advances in acetylene chemistry
^ Cite error: The named reference kroto was invoked but never defined (see the help page).
^ Akagi, K.; Nishiguchi, M.; Shirakawa, H.; Furukawa, Y.; et al. (1987). "One-dimensional conjugated carbyne — synthesis and properties". Synthetic Metals. 17 (1–3): 557–562. doi:10.1016/0379-6779(87)90798-3.
^ Bryce, Martin R. (2021). "A review of functional linear carbon chains (oligoynes, polyynes, cumulenes) and their applications as molecular wires in molecular electronics and optoelectronics". J. Mater. Chem. C. 9 (33): 10524–10546. doi:10.1039/d1tc01406d. ISSN 2050-7526. S2CID 235456429.

[Blacklock2008-1] Cite error: The named reference Blacklock2008 was invoked but never defined (see the help page).

[gibt-2] Gibtner, Thomas; Hampel, Frank; Gisselbrecht, Jean-Paul; Hirsch, Andreas (2002). "End-cap stabilized oligoynes: Model compounds for the linear sp carbon allotrope carbyne". Chemistry: A European Journal. 8 (2): 408–432. doi:10.1002/1521-3765(20020118)8:2<408::AID-CHEM408>3.0.CO;2-L. PMID 11843154.

[Heimann-3] Heimann, R.B.; Evsyukov, S.E.; Kavan, L., eds. (1999). Carbyne and carbynoid structures. Physics and Chemistry of Materials with Low-Dimensional Structures. Vol. 21. p. 452. ISBN 978-0-7923-5323-2.

[chalif1-4] Chalifoux, Wesley A.; Tykwinski, Rik R. (2009). "Synthesis of extended polyynes: Toward carbyne". Comptes Rendus Chimie. 12 (3–4): 341–358. doi:10.1016/j.crci.2008.10.004. In Avancés récentes en chimie des acétylènes – Recent advances in acetylene chemistry

[kroto-5] Cite error: The named reference kroto was invoked but never defined (see the help page).

[akagi-6] Akagi, K.; Nishiguchi, M.; Shirakawa, H.; Furukawa, Y.; et al. (1987). "One-dimensional conjugated carbyne — synthesis and properties". Synthetic Metals. 17 (1–3): 557–562. doi:10.1016/0379-6779(87)90798-3.

[Bryce_2021-7] Bryce, Martin R. (2021). "A review of functional linear carbon chains (oligoynes, polyynes, cumulenes) and their applications as molecular wires in molecular electronics and optoelectronics". J. Mater. Chem. C. 9 (33): 10524–10546. doi:10.1039/d1tc01406d. ISSN 2050-7526. S2CID 235456429.

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