Selective ozone activation of phenanthrene in liquid CO 2 .
Honghong ShiMichael LundinAndrew DanbyEden P GoAbhimanyu PatilHuaxing ZhouTimothy A JacksonBala SubramaniamPublished in: RSC advances (2021)
We demonstrate liquid CO 2 (8 °C, 4.4 MPa) as a benign medium to perform safe ozonolysis of phenanthrene at near-ambient temperatures. The ozonolysis products consist of several monomeric oxidation products such as diphenaldehyde, diphenic acid and phenanthrenequinone as well as polymeric structures up to 1130 Da. The observed chemical shifts ( 1 H-6.03 ppm, 13 C-104.38 ppm) in 2D-NMR spectra of the products confirm the formation of secondary ozonide. Based on the range of observed products, a Criegee-type mechanism is proposed. The ability to deconstruct phenanthrene and produce oxygenated precursors via this technique is particularly of interest in creating new materials from aromatic moieties.