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Synthesis

Chemistry in Pictures: Green flow

by Craig Bettenhausen
April 24, 2020

Credit: Submitted by Chris Thomson, PhD Student at Heriot-Watt University, Edinburgh; @C_G_Thomson, @VilelaLAB

Singlet oxygen (1O2) is a useful synthetic reagent. It is a more reactive, electronically excited version of the normal triplet oxygen (3O2). But you can’t just buy a bottle of the stuff, even from a chemical company. You need to make it and use it right away, while it’s still excited. One way to make it is to use a light-sensitive compound known as a photosensitizer. This clip shows one based on a molecule called BODIPY being used in a flow reactor. The light excites the BODIPY, which transfers its energy to oxygen to create singlet oxygen. Here, the singlet oxygen turns a-terpinene, a natural product extracted from pine needles that smells of a pine forest, into ascaridole, which can be used as medicine to kill parasitic worms. The flow reaction approach increases the contact between the liquid phase (chloroform) and the oxygen in the air, and ensures that the BODIPY gets plenty of light.

Read the related paper here: J. Flow Chem. 2020, DOI: 10.1007/s41981-019-00067-4.

Submitted by Chris Thomson, PhD Student at Heriot-Watt University, Edinburgh; @C_G_Thomson, @VilelaLAB

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