The template-directed synthesis of a catenane, in which the interlocking rings are bisparaphenylene-34-crown-10 (BPP34C10) and a cyclobis (paraquat-p-phenylene) tetracationic macrocycle, is reported to occur when 4,4′ -bipyridine and 1,4-bis(bromomethyl)benzene are added to a solution of BPP34C10 in dimethylformamide. This remarkable act of self-assembly, which requires the coming together of five molecular components, is rationalised in terms of the mutual recognition properties displayed by the individual parts of a compound undergoing construction in a modular manner.
The next step in the research effort of the Amsterdam researchers towards lasso peptide synthesis will be to introduce easily breakable bonds in the quasicatenane, so that the rings can be unlocked.
Templated Synthesis of a Catenane | Fabien …
Luuk Steemers, Martin J. Wanner, Martin Lutz, Henk Hiemstra & Jan H. van Maarseveen: Synthesis of spiro quasicatenanes and quasirotaxanes via a templated backfolding strategy. Nature Communications, published online 25 May 2017. .
Active Metal Template Synthesis of  ..
Chemists at the University of Amsterdam's Van 't Hoff Institute for Molecular Sciences have discovered a new class of molecules. This week they report in Nature Communications on their synthesis method leading to 'quasicatenanes': pretzel-like molecules consisting of two molecular rings 'oppositely' coupled at a central carbon atom. The discovery is an important step towards synthesis of lasso peptides; new molecules with a potential use as medicines.
Nian Lin's group at HKUST - HKUST Department of …
Catenanes – molecules consisting of interlocked macrocyclic rings – have been prepared by templation strategies for some thirty years. The utilization of CuI cation, aromatic donor–acceptor interactions and hydrogen bonding assisted self-assembly strategies has led to the construction of numerous examples of these aesthetically pleasing species. This review seeks to discuss key developments in the synthesis and functional application of catenanes that have occurred since the Millennium. The much expanded range of metal cation templates; the genesis and growth of anion templation, as well as the use of alternative supramolecular interactions (halogen bonding and radical templation) and thermodynamically controlled reactions to synthesize catenanes are detailed. The class of catenanes that may be described as “molecular machines” are then highlighted and to conclude, attempts to fabricate catenanes onto surfaces and into metal organic frameworks (MOFs) are discussed.
Hydrogen-Bond-Mediated Template Synthesis of …
A new type of neutral donor–acceptor -catenane, containing both complementary units in the same ring was synthesized from a dynamic combinatorial library in water. The yield of the water soluble -catenane is enhanced by increasing either building-block concentrations or ionic strength, or by the addition of an electron-rich template. NMR spectroscopy demonstrates that the template is intercalated between the 2 electron-deficient naphthalenediimide units of the catenane.