Benke BP,
Kirschbaum T,
Graf J,
Gross JH,
Mastalerz M.
*
Ruprecht-Karls-Universität Heidelberg, Germany
Dimeric and Trimeric Catenation of Giant Chiral [8 + 12] Imine Cubes Driven by Weak
Supramolecular Interactions.
Nat. Chem. 2023;
15: 413-423
DOI:
10.1038/s41557-022-01094-w
Key words
catenanes - chiral cubes - catenated cubes - imine condensation
Significance
Catenanes are at the forefront of research efforts for fabricating molecular machines
and intelligent materials. Among the various synthetic tactics developed, aromatic
stacking interactions represents the most widely used operating driving force for
assembling. Here, the authors report a distinct approach to both monomeric and catenated
cages, which are directed by weak dispersion interactions and solvophobic effects.
Comment
Taking 1,4-disubstituted terephthalaldehydes as edges and chiral triamino-tribenzotriquinacenes
as vertices, a series of giant [8+12] cubes are successfully obtained via imine condensations.
Systematic investigations further indicate that the catenation processes are mainly
promoted by dispersion forces among the substituents, such as methoxy and methylthio
on terephthalaldehydes, rather than the π–π stacking interactions.
