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

被引：148

作者：

Della Sala, Paolo ^{[1
]}

Del Regno, Rocco ^{[1
]}

Talotta, Carmen ^{[1
]}

Capobianco, Amedeo ^{[1
]}

Hickey, Neal ^{[2
]}

Geremia, Silvano ^{[2
]}

De Rosa, Margherita ^{[1
]}

Spinella, Aldo ^{[1
]}

Soriente, Annunziata ^{[1
]}

Neri, Placido ^{[1
]}

Gaeta, Carmine ^{[1
]}

机构：

[1] Univ Salerno, Dipartimento Chim & Biol A Zambelli, Lab Supramol Chem, Via Giovanni Paolo II 132, I-84084 Fisciano, SA, Italy

[2] Univ Trieste, Ctr Eccellenza Biocristallog, Dipartimento Sci Chim & Farmaceut, Via L Giorgieri 1, I-34127 Trieste, Italy

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2020年 / 142卷 / 04期

关键词：

HIGH-YIELD SYNTHESIS; CONVERSION; FACILE;

D O I：

10.1021/jacs.9b12216

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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

引用

页码：1752 / 1756

页数：5

共 23 条

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