期刊
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
卷 8, 期 -, 页码 967-976出版社
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.8.109
关键词
amides; anion recognition; chirality; macrocycles; molecular switches; supramolecular chemistry
资金
- University of Pavia
- University of Messina
- MIUR (Programs of National Relevant Interest PRIN) [2004-033354, 2009-A5Y3N9]
- CINECA Supercomputer Center
- ISCRA NANOCHIR project [HP10CKIGGH]
- CARIPLO Foundation
- INSTM-Regione Lombardia
We report on the synthesis and characterization of novel shape-persistent, optically active arylamide macrocycles, which can be obtained using a one-pot methodology. Resolved, axially chiral binol scaffolds, which incorporate either methoxy or acetoxy functionalities in the 2,2' positions and carboxylic functionalities in the external 3,3' positions, were used as the source of chirality. Two of these binaphthyls are joined through amidation reactions using rigid diaryl amines of differing shapes, to give homochiral tetraamidic macrocycles. The recognition properties of these supramolecular receptors have been analyzed, and the results indicate a modulation of binding affinities towards dicarboxylate anions, with a drastic change of binding mode depending on the steric and electronic features of the functional groups in the 2,2' positions.
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