Green Synthesis of Soluble Polysilsesquioxane with Phthalimide Groups

Int J Mol Sci. 2023 Dec 19;25(1):57. doi: 10.3390/ijms25010057.

Abstract

Soluble polysilsesquioxane containing side-chain phthalimide groups (PSQ-PhI) was synthesized via a solvent- and catalyst-free hydrolytic polycondensation reaction using 2-[3-(triethoxysilyl)propyl]-1H-isoindole-1,3(2H)-dione. The composition and structure of polysilsesquioxane was confirmed via 1H, 13C, and 29Si NMR spectroscopy, Fourier transform infrared spectroscopy, gel permeation chromatography, thermogravimetric analysis, dynamic light scattering, X-ray diffraction analysis, and elemental analysis. The synthesized silsesquioxane showed a monomodal molecular weight distribution. The average molecular weight of polysilsesquioxane is 11,200 Da, and the polydispersity index is 1.10. 29Si NMR analysis showed a half-peak width w1/2 3.1 ppm at δ -68.3, which corresponds to the PhI(CH2)3SiO3/2 unit and indicates an ordered structure in the polymer, with some defects caused by the presence of uncondensed silanol groups. PSQ-PhI showed good thermal stability (Td5% decomposition at 345 °C). The polysilsesquioxane-based coating was transparent in the visible region.

Keywords: hydrolytic polycondensation; phthalimide; polysilsesquioxane.

MeSH terms

  • Chromatography, Gel
  • Isoindoles*
  • Organosilicon Compounds*
  • Phthalimides*

Substances

  • polysilsesquioxane
  • phthalimide
  • Phthalimides
  • Isoindoles
  • Organosilicon Compounds