Monoaminophosphorylated pillar[5]arenes as hosts for alkaneamines

For the first time, monofunctionalized pillar[5]arenes containing a 1-aminophosphonate fragment have been obtained and characterized. As shown by NMR spectroscopy, the replacement of the amino groups by 1-aminophosphonate units in the macrocycle structure allows switching of “self-assembling–host–guest complexation” properties of the monofunctionalized pillar[5]arenes. Thus, new synthesized aminophosphonated pillar[5]arenes form host–guest complexes with aliphatic amines contrary to monoamine macrocycles that tend to self-assemble.