Staffane

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title: "Staffane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["polycyclic-nonaromatic-hydrocarbons"] description: "Polycyclic hydrocarbon" topic_path: "general/polycyclic-nonaromatic-hydrocarbons" source: "https://en.wikipedia.org/wiki/Staffane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Polycyclic hydrocarbon ::

::figure[src="https://upload.wikimedia.org/wikipedia/commons/2/21/Staffane.svg" caption="[n]staffane"] ::

A staffane or [n]staffane is an organic compound, a polycyclic hydrocarbon with molecular structure H-[-C≡(-CH2-)3≡C-]n-H, for some integer n ≥ 1. The chemical formula is therefore C5nH6n+2

Staffanes were first obtained in 1988 by Piotr Kaszyński and Josef Michl, by spontaneous polymerization of [1.1.1]-propellane C5H6 or C2(=CH2)3. In the reaction, the axial C-C bond of the propellane (the "bridge") is broken, creating a free bond on each of the two axial carbons (the "bridgeheads"). The resulting structural unit [-C≡(-CH2-)3≡C-] is a rigid cage, consisting of two carbon atoms joined by three methylene bridges; therefore the joined units are constrained to lie on a straight line. This feature has generated substantial interest among nanotechnology researchers, who have considered staffane oligomers as convenient "rigid rods" for building all sorts of nanostructures.

An oligomer with a specific number n of units is named [n]staffane (e.g., [1]staffane is bicyclo[1.1.1]pentane, [2]staffane, etc.) The notation [n]staffane is used when the number of units is variable or unspecified; in this case the "n" in the brackets is not a variable, but the letter "n" iself, and therefore considered part of the name.

References

References

1. (1988). "[n]Staffanes: A molecular-size "Tinkertoy" construction set for nanotechnology. Preparation of end-functionalized telomers and a polymer of [1.1.1]propellane". Journal of the American Chemical Society.

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