Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides
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 c...
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doaj-285a5769a20647b48648ad8bd44368982021-02-02T01:35:20ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-06-018196797610.3762/bjoc.8.1091860-5397-8-109Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amidesMarco Caricato0Nerea Jordana Leza1Claudia Gargiulli2Giuseppe Gattuso3Daniele Dondi4Dario Pasini5Department of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, ItalyDepartment of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, ItalyDepartment of Organic and Biological Chemistry, University of Messina, Viale F. Stagno d'Alcontres 31, 98166 Messina, ItalyDepartment of Organic and Biological Chemistry, University of Messina, Viale F. Stagno d'Alcontres 31, 98166 Messina, ItalyDepartment of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, ItalyDepartment of Chemistry, University of Pavia, Viale Taramelli 10, 27100 Pavia, ItalyWe 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.https://doi.org/10.3762/bjoc.8.109amidesanion recognitionchiralitymacrocyclesmolecular switchessupramolecular chemistry |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Marco Caricato Nerea Jordana Leza Claudia Gargiulli Giuseppe Gattuso Daniele Dondi Dario Pasini |
spellingShingle |
Marco Caricato Nerea Jordana Leza Claudia Gargiulli Giuseppe Gattuso Daniele Dondi Dario Pasini Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides Beilstein Journal of Organic Chemistry amides anion recognition chirality macrocycles molecular switches supramolecular chemistry |
author_facet |
Marco Caricato Nerea Jordana Leza Claudia Gargiulli Giuseppe Gattuso Daniele Dondi Dario Pasini |
author_sort |
Marco Caricato |
title |
Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides |
title_short |
Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides |
title_full |
Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides |
title_fullStr |
Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides |
title_full_unstemmed |
Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides |
title_sort |
synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides |
publisher |
Beilstein-Institut |
series |
Beilstein Journal of Organic Chemistry |
issn |
1860-5397 |
publishDate |
2012-06-01 |
description |
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. |
topic |
amides anion recognition chirality macrocycles molecular switches supramolecular chemistry |
url |
https://doi.org/10.3762/bjoc.8.109 |
work_keys_str_mv |
AT marcocaricato synthesisandanionrecognitionpropertiesofshapepersistentbinaphthylcontainingchiralmacrocyclicamides AT nereajordanaleza synthesisandanionrecognitionpropertiesofshapepersistentbinaphthylcontainingchiralmacrocyclicamides AT claudiagargiulli synthesisandanionrecognitionpropertiesofshapepersistentbinaphthylcontainingchiralmacrocyclicamides AT giuseppegattuso synthesisandanionrecognitionpropertiesofshapepersistentbinaphthylcontainingchiralmacrocyclicamides AT danieledondi synthesisandanionrecognitionpropertiesofshapepersistentbinaphthylcontainingchiralmacrocyclicamides AT dariopasini synthesisandanionrecognitionpropertiesofshapepersistentbinaphthylcontainingchiralmacrocyclicamides |
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1724311470227849216 |