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

Published on 2020-01-14T22:43:41Z (GMT) by
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 <b>1</b> or the prism[6]­arene <b>3</b> 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 <b>2</b> 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 <sup>+</sup>NC–H···π interactions. This recognition motif is the basis of the templated synthesis of the prism­[<i>n</i>]­arenes here reported.

Cite this collection

Della Sala, Paolo; Del Regno, Rocco; Talotta, Carmen; Capobianco, Amedeo; Hickey, Neal; Geremia, Silvano; et al. (2020): Prismarenes:

A New Class of Macrocyclic Hosts Obtained

by Templation in a Thermodynamically Controlled Synthesis. ACS Publications. Collection. https://doi.org/10.1021/jacs.9b12216