Kenji Caprice, Marion Pupier, Anneli Kruve, Christoph A. Schalley and Fabien B. L. Cougnon
Chem. Sci., 2018,9, 1317-1322
DOI:
10.1039/C7SC04901C,
Edge Article
We report the efficient condensation of imine-based macrocycles from dialdehyde A and aliphatic diamines Bn in pure water. Within the libraries, we identified a family of homologous amphiphilic [2]catenanes, whose self-assembly is primarily driven by the hydrophobic effect. The length and odd-even character of the diamine alkyl linker dictate both the yield and the conformation of the [2]catenanes, whose particular thermodynamic stability further shifts the overall equilibrium in favour of imine condensation. These findings highlight the role played by solvophobic effects in the self-assembly of complex architectures.