Examination of the Dynamic Covalent Chemistry of [2 + 3]-Imine Cages

The
synthesis of shape-persistent organic cage compounds by the
formation of imine bonds opens the possibility to realize cages of
different sizes, geometries, topologies, and functions. It is generally
assumed that the imine bond is rather chemically labile allowing a
self-correction mechanism until thermodynamic equilibrium is reached,
which is often the case if a cage is formed. However, there are some
contradictory experimental data to this assumption. To get a deeper
insight into the imine bond dynamics of covalent organic cages, we
studied the formation and exchange of both dialdehydes and triamines
of two different [2 + 3] imine cages with the aid of a deuterated
dialdehyde molecular building block.