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Chiral nanostructuring of multivalent macrocycles in solution and on surfaces

Caricato, M., Deforge, A., Bonifazi, Davide, Dondi, D., Mazzanti, Andrea and Pasini, Dario 2015. Chiral nanostructuring of multivalent macrocycles in solution and on surfaces. Organic & Biomolecular Chemistry 13 , pp. 3593-3601. 10.1039/c4ob02643h

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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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Royal Society of Chemistry
ISSN: 1477-0520
Date of First Compliant Deposit: 15 April 2016
Date of Acceptance: 19 January 2015
Last Modified: 04 Jun 2017 08:41

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