US EPA

3230214 

Journal Article 

Macrocyclic tetraimines: Synthesis and reversible uptake of diethyl phthalate by a porous macrocycle 

Sanna, E; Escudero-Adán, EC; López, C; Ballester, P; Rotger, C; Costa, A 

2016 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

American Chemical Society 

81 

12 

5173-5180 

English 

27200454 

10.1021/acs.joc.6b00768 

WOS:000378302900027 

is supplemented by 3479713 - Supplementary material

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.