Synthesis, self-assembly and the effect of the macrocyclic platform on thermal properties of lactic acid oligomer modified by p-tert-butylthiacalix[4]arene

Abstract

© 2019 Elsevier B.V. The interaction of (L)-lactic acid with p-tert-butylthiacalix[4]arene containing ethoxycarbonyl fragments in the 1,3-alternate conformation was studied in tetraglyme. For the first time, the lactic acid oligomer was obtained by polycondensation with the macrocycle and characterized by 1 H, 13 C NMR, IR spectroscopy, MALDI mass spectrometry and gel permeation chromatography. Thermal stability of the obtained copolyester of lactic acid and thiacalix[4]arene was studied by TG/DSC analysis and the effect of the macrocyclic platform on its thermal properties was shown. Copolyester obtained was thermally more stable than oligolactic acid. Self-assembly of synthesized oligomer was studied by dynamic light scattering method. It was shown that monodisperse particles (PDI = 0.13) with the size of 208 ± 4 nm are formed in CH 3 CN solution at 2.5 × 10 −5 M concentration.