191-48-0Relevant articles and documents
Acenaphthyne
Chapman, O. L.,Gano, J.,West, P. R.,Regitz, M.,Maas, G.
, p. 7033 - 7036 (1981)
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Tridecacyclene: A Cyclic Tetramer of Acenaphthylene
Sumy, Daniel P.,Dodge, Nicholas J.,Harrison, Chloe M.,Finke, Aaron D.,Whalley, Adam C.
, p. 4709 - 4712 (2016)
In this manuscript, we describe the single-step preparation of a cyclic tetramer of acenaphthylene through a Lewis acid-catalyzed aldol cyclization of 1-acenaphthenone. The previously unexplored cyclic tetramer material differs from the better-known cyclic trimer, decacyclene, due to the presence of a central eight-membered ring. This ring not only forces the molecule to distort significantly from planarity, but is also responsible for its unique electronic properties, including a decrease in the reduction potential (by about 0.4 eV) and optical gap (by about 0.73 eV), compared to the more planar decacyclene. The synthesized compound crystallizes into a unique packing structure with significant π-stacking observed between adjacent molecules. Furthermore, due to its saddle-like shape, the cyclic tetramer is able to form shape-complementary interactions between its concave surface and the convex outer surface of buckminsterfullerene to generate cocrystalline supramolecular assemblies. What a catch! A cyclic tetramer of acenaphthylene was synthesized in a single step. The compound exhibits interesting electronic and structural properties when compared to the better-known cyclic trimer due to the presence of a central eight-membered ring. The saddle-like shape of cyclic tetramer allows it to form cocrystalline supramolecular assemblies with C60 in the solid state (see scheme).
Study of structural aspects of thermochemical conversions of compounds modeling oligophenylenes containing acenaphthylenyl and acenaphthenyl groups
Kovalev, A. I.,Balykova, T. N.,Lindeman, S. V.,Teplyakov, M. M.,Khotina, I. A.,et al.
, p. 790 - 798 (1994)
With the aim of elucidating the mechanism of the thermochemical conversion of oligophenylenes containing acenaphthylenyl groups, the thermolysis of model compounds: 1,3,5-tris(5-acenaphthylenyl)benzene (1), 1,3,5-tris(5-acenaphthenyl)benzene (2), acenaphthylene, and acenaphthene, was studied by differential thermal analysis (DTA), dynamic thermogravimetric analysis (TGA), and mass spectrometry.Compounds 1 and 2 were studied by X-ray structural analysis.A scheme for the formation of secondary structures was suggested.Optimum temperature conditions were found for preparing thermostable, heat-resistant, and stable to thermooxidation polymers based on compounds containing the acenaphthylenyl groups. - Key words: 1,3,5-tris(acenaphthylenyl)benzene, 1,3,5-tris(acenaphthenyl)benzene, acenaphthylene, acenaphthene, thermochemical conversions; decacyclene; polymers, thermal properties; X-ray structural analysis.
Novel Syntheses of Decacyclene by Deoxygenating Cyclotrimerisation of Acenaphthenequinone with Zero-valent Titanium or Phosphorus Pentasulfide
Zimmermann, Klaus,Haenel, Matthias W.
, p. 609 - 611 (2007/10/03)
Decacyclene (2) was obtained in 15-21% yield by reaction of acenaphthenequinone (6) with bis(η6-biphenyl)titanium(0) (9) in toluene or diglyme at 110°C and in 18% yield by reaction of 6 with phosphorus pentasulfide in boiling toluene. The new reactions are used to attempt the conversion of 3,8-dibromoacenaphthenequinone (7) to 3,4,9,10,15,16-hexabromodecacyclene (3) which is considered to serve as a suitable precursor for the bowl-shaped polycyclic aromatic hydrocarbon C 36H12 (1).
