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 Ï-electron-rich aromatic cavity that exhibits a great affinity for the quaternary ammonium guests, originating from favorable cation···πand +NC-H···πinteractions. This recognition motif is the basis of the templated synthesis of the prism[n]arenes here reported.

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

Hickey N.;Geremia S.;
2020-01-01

Abstract

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 Ï-electron-rich aromatic cavity that exhibits a great affinity for the quaternary ammonium guests, originating from favorable cation···πand +NC-H···πinteractions. This recognition motif is the basis of the templated synthesis of the prism[n]arenes here reported.
2020
3-gen-2020
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https://pubs.acs.org/doi/abs/10.1021/jacs.9b12216
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11368/2964132
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