Aliphatic Poly(ether amide)s by Polycondensation of Activated Sebacic Acid Derivatives

Poly(ether amide)s were prepared by polycondensation of 1,13‐diamino‐4,7,11‐trioxatridecane (DTT) with the bisimidazolide or with the bis N‐hydroxysuccinimide ester of sebacic acid. Four different solvents and three different temperatures were compared. The highest molecular weights were obtained with the bisimidazolide in dimethylsulfoxide (DMSO) at 60°C. MALDI‐TOF mass spectra revealed the existence of cyclic oligoamides and polyamides in all samples. The molar fraction of cycles considerably increased with higher molecular weights of the entire sample. The polycondensations were repeated under optimum conditions in the presence of α‐cyclodextrin to prepare polydisperse catenanes consisting of α‐cyclodextrin threaded on cyclic polyamides. Yet, despite broad variation of the reaction conditions, only cylic polyamides free of cyclodextrin were isolated. Furthermore, a pseudorotaxane was prepared from DTT and α‐cyclodetrin and polycondensed with bis‐(4‐chlorophenyl)sebacate. Again, only cyclic polyamides free of cyclodextrin were detectable.