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Continuous and Scalable Synthesis of a Porous Organic Cage by Twin Screw Extrusion (TSE)

preprint
submitted on 31.03.2020 and posted on 01.04.2020 by Benjamin Egleston, Michael C. Brand, Francesca Greenwell, Michael E. Briggs, Stuart L. James, Andrew I. Cooper, Deborah E. Crawford, Rebecca L. Greenaway
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.

Funding

EP/R005710/1

EP/R005540/1

ERC FP7 Agreement No. 321156

Royal Society University Research Fellowship

History

Email Address of Submitting Author

rebecca.greenaway@liverpool.ac.uk

Institution

University of Liverpool

Country

UK

ORCID For Submitting Author

0000-0003-1541-4399

Declaration of Conflict of Interest

No conflict of interest

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