The use of three-dimensional (3D) printing has been a growing field in the scientific community for several years now, with applications focused on tissue engineering, electronics, microfluidics and pneumatics. However, 3D printing technology in organic chemistry still has many hurdles to overcome. The comparatively low cost of 3D printers and polymer supplies enables chemical discovery without the need for expensive laboratory equipment. The ease of computer-aided design allows for modifications to be made within minutes, and within a few hours, the device is ready for use. When these techniques are paired with the efficiency of flow chemistry, the result can be tailored flow cells that are optimal for specific applications. We explored various polymer materials to print flow cells along with utilizing different designs created using AutoCAD, Simplify3D and Qidi Tech software, then tested these cells with a set of photochemical control reactions. In particular, the 3D printed flow cells were evaluated for chemical compatibility and robustness. From our current designs, the SLA cell yielded the most product in the photooxygenation of a model thienopyridone. Although we were able to obtain product from both SLA and PP cells, pre-reaction rinses with HCl, water and methanol were crucial to the success of the process because they removed residual polymers left over from the printing process. Based on these optimizations, we customized a set of flow cells for a cartridge in-flow photooxygenation process that reduced the residence time under blue LED light irradiation from several hours to 10 min. The robustness of the process was tested in the gram-scale photooxygenation of 7-aminothieno[3,2-c]pyridin-4(5H)-ones to produce PTP4A3 phosphatase inhibitors, 7-iminothieno[3,2- c]pyridine-4,6(5H,7H)-diones.

Photooxygenation in 3D printed flow cells

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.