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Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides

Marco Caricato, Nerea Jordana Leza, Claudia Gargiulli, Giuseppe Gattuso, Daniele Dondi and Dario Pasini

Beilstein J. Org. Chem. 2012, 8, 967–976. https://doi.org/10.3762/bjoc.8.109

Supporting Information

Supporting Information File 1: Additional NMR and MS spectra for the macrocyles, and Cartesian coordinates for the calculated geometries discussed in the paper.
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Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides

Marco Caricato, Nerea Jordana Leza, Claudia Gargiulli, Giuseppe Gattuso, Daniele Dondi and Dario Pasini

Beilstein J. Org. Chem. 2012, 8, 967–976. https://doi.org/10.3762/bjoc.8.109

How to Cite

Caricato, M.; Leza, N. J.; Gargiulli, C.; Gattuso, G.; Dondi, D.; Pasini, D. Beilstein J. Org. Chem. 2012, 8, 967–976. doi:10.3762/bjoc.8.109

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TY  - JOUR
A1  - Caricato, Marco
A1  - Leza, Nerea Jordana
A1  - Gargiulli, Claudia
A1  - Gattuso, Giuseppe
A1  - Dondi, Daniele
A1  - Pasini, Dario
T1  - Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides
JF  - Beilstein Journal of Organic Chemistry
PY  - 2012///
VL  - 8
SP  - 967
EP  - 976
SN  - 1860-5397
DO  - 10.3762/bjoc.8.109
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.8.109
KW  - amides
KW  - anion recognition
KW  - chirality
KW  - macrocycles
KW  - molecular switches
KW  - supramolecular chemistry
N2  - 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.
ER  -

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