Macrocyclic Tetraimines: Synthesis and Reversible Uptake of Diethyl Phthalate by a Porous Macrocycle

The imine bond has attracted much
attention for the synthesis of
macrocycles used to construct porous materials. In the present article,
we report on the synthesis of two series of isomeric macrocyclic tetraimines
based on bis-alkynylbenzene diamines. Under heterogeneous solid–liquid
conditions the condensation of the diamines with isophthalaldehyde
or terephthaldehyde afforded mainly the corresponding [2 + 2] adducts.
Among the eight macrocycles studied, only the macrocycle 1 has a porous structure. The article describes not only the synthesis
of these macrocycles but also the encountered difficulties during
their preparation. Finally, we expand the use of 1a as
a porous solid support by studying its reversible and preferential
liquid–solid adsorption properties for diethyl phthalate in
front of other commercial phthalates.