Controlling the Size and Morphology of Supramolecular Assemblies of Viologen-Resorcin[4]arene Cavitands

• Published in: Chemistry : a European journal 2014-10, Vol.20 (43), p.14018-14025
• Main Authors: Kashapov, Ruslan R., Kharlamov, Sergey V., Sultanova, Elza D., Mukhitova, Rezeda K., Kudryashova, Yuliana R., Zakharova, Lucia Y., Ziganshina, Albina Y., Konovalov, Alexander I.
• Format: Article
• Language: English
• Subjects: Assemblies; cavitands; Chemistry; Controlled release; Entrapment; Formations; hydrophobic effect; Hydrophobicity; Iodides; nanocontainers; Nanostructure; Self assembly; supramolecular chemistry
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201403721

A novel class of self‐assembling nanoparticles is formed with viologen–resorcin[4]arene cavitands; the association model is strongly controlled by their hydrophobicity. Interestingly, the cavitand assemblies are designed through click chemistry to form self‐assembled noncovalently connected aggregates through counterion displacement. The iodide and benzoate ions are utilized as strongly polarizable counterions to induce cavitand self‐assembly. The counterion‐mediated decrease in hydrophilicity of the viologen–resorcin[4]arenes is the underlying trigger to induce particle formation. These particles can be used as nanocontainers and find their applications in delivery systems. Self‐contained: The role of amphiphilic viologen‐based nanoarchitectures and counterions on determining the nature of particle formation was shown. The finding that cavitand assembly depends on a hydrophobic tail length and counterion size may be exploited in the optimized designs of nanocontainers for the entrapment and controlled release of hydrophobic compounds (see figure; BA=benzoic acid).