Thionyl Chloride-Catalyzed Preparation of Microporous Organic Polymers through Aldol Condensation

Abstract

We demonstrated the synthesis of five kinds of microporous organic polymers based on aldol self-condensation of di- and multiacetyl-containing building blocks catalyzed by thionyl chloride. The α,β-unsaturated ketone (dimerization) and 1,3,5-trisubstituted benzene (cyclotrimerization) can be observed in the resulting polymers by Fourier transform infrared and solid-state 13C CP/MAS NMR spectroscopy. The regular spheres and nanometer-scaled cavities were also seen from scanning electron microscopy and high-resolution transmission electron microscopy images. The highest Brunauer–Emmet–Teller specific surface area up to 832 m2 g–1 was obtained for the resulting polymers with a pore volume of 0.48 cm3 g–1. The polymers show great hydrogen storage capacities (up to 1.56 wt %) at 77 K and 1 bar. These excellent characteristics would make them become promising candidates for heterogeneous catalysis, separation, and gas storage.