Stable Pyrene-Based Metal-Organic Framework for Cyclization of Propargylic Amines with CO2 and Detection of Antibiotics in Water

A pyrene-based metal-organic framework, Cd-2(PTTB)(H2O)(2) (WYU-11), was synthesized from the tetracarboxylic pyrene ligand H4PTTB (H4PTTB = 1,3,6,8-tetrakis(3-carboxyphenyl)pyrene) and Cd(NO3)(2) center dot 4H(2)O. Powder X-ray diffraction analysis discloses that the framework is stable in acid, base, and various organic solvent environments. WYU-11 shows excellent catalytic performance on the cyclization reaction of propargylic amines with CO2 into 2-oxazolidinones under mild conditions (60 degree celsius, atmospheric CO2). H-1 NMR studies unveiled that WYU-11 and 1,1,3,3-tetramethylguanidine (TMG) can synergistically activate the propargylic amine substrate and promote the reaction. Importantly, WYU-11 represents a rare example of noble metal-free heterogeneous catalyst that can catalyze the cyclization of CO2 with propargylic amines. In addition, by virtue of the excellent water stability and luminescence properties, WYU-11 shows excellent detection performance for sulfathiazole (STZ) and ornidazole (ODZ) in water. Investigation reveals that the coexistence of photoinduced electron transfer and internal filtering effect could reasonably explain the luminescence quenching of WYU-11 by the antibiotics.

Automated summary

A pyrene-based metal-organic framework, Cd-2(PTTB)(H2O)(2) (WYU-11), was synthesized and found to exhibit stability in various environments. It showed excellent catalytic performance in the cyclization reaction of propargylic amines with CO2 and demonstrated outstanding water stability and luminescence properties for detection of sulfathiazole and ornidazole.