Hierarchical self-assembly of amphiphilic calix[6]arene wheels and viologen axles in water

Rocco Bussolati; Pasquale Carrieri; Andrea Secchi; Arturo Arduini; Alberto Credi; Monica Semeraro; Margherita Venturi; Serena Silvi; Diana Velluto; Romina Zappacosta; Antonella Fontana

doi:10.1039/C3OB40739J

Hierarchical self-assembly of amphiphilic calix[6]arene wheels and viologen axles in water†‡

Rocco Bussolati,^a Pasquale Carrieri,^a Andrea Secchi,^a Arturo Arduini,*^a Alberto Credi,^b Monica Semeraro,^b Margherita Venturi,^b Serena Silvi,*^b Diana Velluto,^c Romina Zappacosta^d and Antonella Fontana*^d

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^a Dipartimento di Chimica, Università di Parma, Parco Area delle Scienze 17/a, I-43124 Parma, Italy
E-mail: arturo.arduini@unipr.it
Fax: +39 0521 905472
Tel: +39 0521 905408

^b Photochemical Nanosciences Laboratory, Dipartimento di Chimica “G. Ciamician”, Università di Bologna, Via Selmi 2, I-40126 Bologna, Italy
E-mail: serena.silvi@unibo.it

^c School of Biological and Chemical Sciences, Queen Mary University of London, Mile End road, London E1 4NS, UK

^d Dipartimento di Farmacia, Università “G. d'Annunzio”, Via dei Vestini, I-66010 Chieti, Italy
E-mail: fontana@unich.it

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 self-aggregation 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.

Organic & Biomolecular Chemistry

Hierarchical self-assembly of amphiphilic calix[6]arene wheels and viologen axles in water†‡

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Hierarchical self-assembly of amphiphilic calix[6]arene wheels and viologen axles in water

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