Continuous and scalable synthesis of a porous organic cage by twin screw extrusion (TSE). Issue 25 (18th May 2020)

• Record Type: Journal Article
• Authors: Egleston, Benjamin D.; Brand, Michael C.; Greenwell, Francesca; Briggs, Michael E.; James, Stuart L.; Cooper, Andrew I.; Crawford, Deborah E.; Greenaway, Rebecca L.
• Is Part Of: Chemical science. Volume 11:Issue 25(2020)
• Page Start: 6582
• Page End: 6589
• Publication Date: 2020-05-18
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc01858a
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : Twin screw extrusion (TSE) is demonstrated as an alternative synthetic method for preparing a prolific porous organic cage. Abstract : The continuous and scalable synthesis of a porous organic cage (CC3 ), obtained through a 10-component imine polycondensation between triformylbenzene and a vicinal diamine, was achieved using twin screw extrusion (TSE). Compared to both batch and flow syntheses, the use of TSE enabled the large scale synthesis of CC3 using minimal solvent and in short reaction times, with liquid-assisted grinding (LAG) also promoting window-to-window crystal packing to form a 3-D diamondoid pore network in the solid state. A new kinetically trapped [3+5] product was also observed alongside the formation of the targeted [4+6] cage species. Post-synthetic purification by Soxhlet extraction of the as-extruded 'technical grade' mixture of CC3 and [3+5] species rendered the material porous.