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Chemistry ; 25(58): 13275-13279, 2019 Oct 17.
Artigo em Inglês | MEDLINE | ID: mdl-31398268

RESUMO

Manipulation of the emerging anion-π interactions in a highly cooperative manner through sophisticated host design represents a very challenging task. In this work, unprecedented tetrahedral anion-π receptors have been successfully constructed for complementary accommodation of tetrahedral and relevant anions. The synthesis was achieved by a macrocycle-directed approach by using large macrocycle precursors bearing four reactive sites, which enabled a kinetic-favored pathway and afforded the otherwise inaccessible tetrahedral cages in considerable yields. Crystal structure suggested that the tetrahedral cages have an enclosed three-dimensional cavity surrounded by four electron-deficient triazine faces in a tetrahedral array. The complementary accommodation of a series of tetrahedral and relevant anions including BF4 - , ClO4 - , H2 PO4 - , HSO4 - , SO4 2- and PF6 - was revealed by ESI-MS and DFT calculations. Crystal structures of ClO4 - and PF6 - complexes showed that the anion was nicely encapsulated within the tetrahedral cavity with up to quadruple cooperative anion-π interactions by an excellent shape and size match. The strong anion-π binding was further confirmed by negative ion photoelectron spectroscopy measurements.


Assuntos
Compostos Macrocíclicos/química , Triazinas/química , Ânions/química , Boratos/química , Reagentes de Ligações Cruzadas/química , Cristalização , Teoria da Densidade Funcional , Estrutura Molecular , Percloratos/química , Espectrometria de Massas por Ionização por Electrospray , Sulfatos/química
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