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1.
Chem Commun (Camb) ; 52(83): 12368-12371, 2016 Oct 11.
Artigo em Inglês | MEDLINE | ID: mdl-27711278

RESUMO

The radical anion and dianion of tridecacyclene (C48H24, 1) have been prepared by reduction with potassium metal. Analysis of the solid-state structure of the dipotassium salt of the dianion (3) reveals evidence of increased aromatic character within the structure's central 8-membered ring despite preservation of the tub-like shape inherent to its neutral parent.

2.
Chemistry ; 22(14): 4709-12, 2016 Mar 24.
Artigo em Inglês | MEDLINE | ID: mdl-26791961

RESUMO

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.


Assuntos
Acenaftenos/síntese química , Ácidos de Lewis/química , Acenaftenos/química , Catálise , Ciclização , Estrutura Molecular
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