Tridecacyclene: A Cyclic Tetramer of Acenaphthylene

Chemistry : a European Journal
Adam Christopher WhalleyAaron D Finke

Abstract

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.

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Citations

Oct 7, 2016·Chemical Communications : Chem Comm·Daniel P SumyAdam C Whalley
Sep 29, 2018·Chemical Communications : Chem Comm·Maymounah Alrayyani, Ognjen Š Miljanić
Dec 10, 2016·The Journal of Organic Chemistry·Robert W MillerAdam C Whalley

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