title: Chiral nanostructuring of multivalent macrocycles in solution and on surfaces.
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 Pd(2+), 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-Pd(2+) hybrid undergoes surface-confined nanostructuring into chiral nanofibres.
authors.affiliation: Department of Chemistry, University of Pavia, Viale Taramelli, 10, 27100, Pavia, Italy. dario.pasini@unipv.it.
authors.forename: Marco
authors.initials: M
authors.lastname: Caricato
authors.forename: Arnaud
authors.initials: A
authors.lastname: Delforge
authors.forename: Davide
authors.initials: D
authors.lastname: Bonifazi
authors.forename: Daniele
authors.initials: D
authors.lastname: Dondi
authors.forename: Andrea
authors.initials: A
authors.lastname: Mazzanti
authors.forename: Dario
authors.initials: D
authors.lastname: Pasini
mesh_terms: D019281:Dimerization; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D018625:Microscopy, Atomic Force; D008958:Models, Molecular; D008968:Molecular Conformation; D049329:Nanostructures / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy; D012996:Solutions; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D013499:Surface Properties
chemical_list: D047028:Macrocyclic Compounds; D012996:Solutions; D010165:Palladium