Chiral nanostructuring of multivalent macrocycles in solution and on surfaces

Marco Caricato, Arnaud Delforge, Davide Bonifazi, Daniele Dondi, Andrea Mazzanti, Dario Pasini

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

We describe the design and synthesis of a novel functionality-rich, homochiral macrocycle, possessing the overall molecular D2 symmetry, in which multivalency is introduced into the covalent framework by means of four suitably positioned pyridine moieties. The macrocycle synthesis is carried out with functionalized, enantiopure 1,1′-binaphthyl synthons as the source of chirality by means of a room temperature esterification reaction as the cyclization procedure. Upon addition of Pd2+, coordination of the pyridine moieties occurs both intra and intermolecularly, to afford chiral ordered mono and dimeric macrocycles or multimeric aggregates depending on the solvents and conditions used. The metal binding event takes place in combination with a significant macrocyclic conformational rearrangement detected by circular dichroism spectroscopy. When in combination with a third component (C60), the macrocycle-Pd2+ hybrid undergoes surface-confined nanostructuring into chiral nanofibres.

langue originaleAnglais
Pages (de - à)3593-3601
Nombre de pages9
journalOrganic and Biomolecular Chemistry
Volume13
Numéro de publication12
Les DOIs
étatPublié - 28 mars 2015

Empreinte digitale

pyridines
Circular dichroism spectroscopy
Nanofibers
Esterification
Chirality
Cyclization
synthesis
Circular Dichroism
chirality
dichroism
Spectrum Analysis
Metals
Temperature
symmetry
room temperature
metals
spectroscopy
pyridine

Citer ceci

Caricato, Marco ; Delforge, Arnaud ; Bonifazi, Davide ; Dondi, Daniele ; Mazzanti, Andrea ; Pasini, Dario. / Chiral nanostructuring of multivalent macrocycles in solution and on surfaces. Dans: Organic and Biomolecular Chemistry. 2015 ; Vol 13, Numéro 12. p. 3593-3601.
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abstract = "We describe the design and synthesis of a novel functionality-rich, homochiral macrocycle, possessing the overall molecular D2 symmetry, in which multivalency is introduced into the covalent framework by means of four suitably positioned pyridine moieties. The macrocycle synthesis is carried out with functionalized, enantiopure 1,1′-binaphthyl synthons as the source of chirality by means of a room temperature esterification reaction as the cyclization procedure. Upon addition of Pd2+, coordination of the pyridine moieties occurs both intra and intermolecularly, to afford chiral ordered mono and dimeric macrocycles or multimeric aggregates depending on the solvents and conditions used. The metal binding event takes place in combination with a significant macrocyclic conformational rearrangement detected by circular dichroism spectroscopy. When in combination with a third component (C60), the macrocycle-Pd2+ hybrid undergoes surface-confined nanostructuring into chiral nanofibres.",
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Chiral nanostructuring of multivalent macrocycles in solution and on surfaces. / Caricato, Marco; Delforge, Arnaud; Bonifazi, Davide; Dondi, Daniele; Mazzanti, Andrea; Pasini, Dario.

Dans: Organic and Biomolecular Chemistry, Vol 13, Numéro 12, 28.03.2015, p. 3593-3601.

Résultats de recherche: Contribution à un journal/une revueArticle

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AU - Pasini, Dario

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