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

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 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.

SUBMITTER: Della Sala P

PROVIDER: S-EPMC7993634 | biostudies-literature | 2020 Jan

REPOSITORIES: biostudies-literature

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

Della Sala Paolo P Del Regno Rocco R Talotta Carmen C Capobianco Amedeo A Hickey Neal N Geremia Silvano S De Rosa Margherita M Spinella Aldo A Soriente Annunziata A Neri Placido P Gaeta Carmine C

Journal of the American Chemical Society 20200115 4

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 c ...[more]

PMID: 31898458

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

Publications

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

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