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Dodecahedrane

About: Dodecahedrane is a research topic. Over the lifetime, 143 publications have been published within this topic receiving 2786 citations. The topic is also known as: hexadecahydro-5,2,1,6,3,4-[2,3]butanediyl[1,4]diylidenedipentaleno[2,1,6-cde:2',1',6'-gha]pentalene & undecacyclo[9.9.0.0(2,9).0(3,7).0(4,20).0(5,18).0(6,16).0(8,15).0(10,14).0(12,19).0(13,17)]icosane.


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Journal ArticleDOI
07 Sep 2000-Nature
TL;DR: It is shown that the cage-structured fullerene C20 can be produced from its perhydrogenated form (dodecahedrane C20H 20) by replacing the hydrogen atoms with relatively weakly bound bromine atoms, followed by gas-phase debromination.
Abstract: Fullerenes are graphitic cage structures incorporating exactly twelve pentagons. The smallest possible fullerene is thus C20, which consists solely of pentagons. But the extreme curvature and reactivity of this structure have led to doubts about its existence and stability. Although theoretical calculations have identified, besides this cage, a bowl and a monocyclic ring isomer as low-energy members of the C20 cluster family, only ring isomers of C20 have been observed so far. Here we show that the cage-structured fullerene C20 can be produced from its perhydrogenated form (dodecahedrane C20H20) by replacing the hydrogen atoms with relatively weakly bound bromine atoms, followed by gas-phase debromination. For comparison we have also produced the bowl isomer of C20 using the same procedure. We characterize the generated C20 clusters using mass-selective anion photoelectron spectroscopy; the observed electron affinities and vibrational structures of these two C20 isomers differ significantly from each other, as well as from those of the known monocyclic isomer. We expect that these unique C20 species will serve as a benchmark test for further theoretical studies.

676 citations

Journal ArticleDOI
TL;DR: By shooting a beam of helium ions at a continuously deposited surface of dodecahdrane, C20H20, this paper incorporated a helium atom into the molecular cage, where it remains trapped.

89 citations

Journal ArticleDOI
TL;DR: The original concept for the synthesis of pentagonal dodecahedranes by the conversion of structurally similar, high-energy pagodanes relied on catalytic dehydrocyclization as discussed by the authors.
Abstract: The original concept for the synthesis of pentagonal dodecahedranes by the conversion of structurally similar, high-energy [1111]pagodanes relied on catalytic dehydrocyclizations As a consequence, preparative limitations were preprogrammed With multiple functionalization of these pagodanes, alternative cyclization methods became viable These efficient processes allowed access to a multitude of pentagonal and nonpentagonal, carba- and heterocyclic dodecahedral skeletons with widely variable substitution patterns Such a roundabout route provided the (CH)20 basic framework with high efficiency, and long-lacking thermochemical data could be ascertained calorimetrically In spite of the unusually pronounced pyramidalization of their olefinic centers, singly and doubly unsaturated dodecahedranes with isolated CC bonds proved to be kinetically quite stable, but underwent dimerization on thermal activation Dodecahedranes with a higher degree of unsaturation (trienes–decaenes, C20 fullerene?) have been found so far only in the gas phase Higher fullerenes, including C60, have been identified by mass spectrometry after exposure of halogenated dodecahedranes and pagodanes to a 248-nm excimer laser Transannular electron delocalization has been verified for the “slender” pagodane/isopagodane and even for the “spherical” dodecahedrane cages

77 citations

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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20201
20173
20162
20152
20143
20132