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Prismarenes: A New Class of Macrocyclic Hosts Obtained by Templation in a Thermodynamically Controlled Synthesis

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posted on 14.01.2020 by Paolo Della Sala, Rocco Del Regno, Carmen Talotta, Amedeo Capobianco, Neal Hickey, Silvano Geremia, Margherita De Rosa, Aldo Spinella, Annunziata Soriente, Placido Neri, Carmine Gaeta
The novel title macrocycles, based on methylene-bridged 1,5-naphthalene units, have been obtained by template effect in a thermodynamically controlled synthesis. In detail, the prism[5]­arene 1 or the prism[6]­arene 3 was selectively removed from the equilibrium mixture by using the complementary ammonium-templating agent. When only the solvent 1,2-DCE was used, the 1,4-confused derivative 2 was obtained. The prism[5]­arene here described shows a deep π-electron-rich aromatic cavity that exhibits a great affinity for the quaternary ammonium guests, originating from favorable cation···π and +NC–H···π interactions. This recognition motif is the basis of the templated synthesis of the prism­[n]­arenes here reported.

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