title: Hierarchical self-assembly of amphiphilic calix[6]arene wheels and viologen axles in water.
abstract: We have designed and synthesized two amphiphilic calix[6]arene derivatives, CA8 and CA18, that combine the potential to act as wheel components for pseudorotaxane structures with the self-assembly features typical of surfactant molecules in aqueous solution. Their endo-cavity recognition and selfaggregation properties were compared with those of a non-amphiphilic analogue, C8. TEM, DLS, and fluorescence experiments show that in water the amphiphilic calixarenes form vesicle- and micelle-like aggregates. The size, nature and properties of such aggregates depend on the length of the alkyl chain anchored at the lower rim of the calix[6]arene skeleton, as well as on the inclusion of a molecular guest into the wheel. Specifically, the release of a fluorescent guest entrapped inside the CA8 vesicles is accelerated in the presence of dioctylviologen axles that can pierce the calixarene cavity.
authors.affiliation: Dipartimento di Chimica, Università di Parma, Parco Area delle Scienze 17/a, I-43124 Parma, Italy. arturo.arduini@unipr.it.
authors.forename: Rocco
authors.initials: R
authors.lastname: Bussolati
authors.forename: Pasquale
authors.initials: P
authors.lastname: Carrieri
authors.forename: Andrea
authors.initials: A
authors.lastname: Secchi
authors.forename: Arturo
authors.initials: A
authors.lastname: Arduini
authors.forename: Alberto
authors.initials: A
authors.lastname: Credi
authors.forename: Monica
authors.initials: M
authors.lastname: Semeraro
authors.forename: Margherita
authors.initials: M
authors.lastname: Venturi
authors.forename: Serena
authors.initials: S
authors.lastname: Silvi
authors.forename: Diana
authors.initials: D
authors.lastname: Velluto
authors.forename: Romina
authors.initials: R
authors.lastname: Zappacosta
authors.forename: Antonella
authors.initials: A
authors.lastname: Fontana
mesh_terms: D047250:Calixarenes / Q000138:chemical synthesis / Q000737:chemistry*; D008823:Micelles; D010636:Phenols / Q000138:chemical synthesis / Q000737:chemistry*; D013501:Surface-Active Agents / Q000138:chemical synthesis / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D008823:Micelles; D010636:Phenols; D013501:Surface-Active Agents; C476540:calix(6)arene; D014867:Water; D047250:Calixarenes