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Mechanochemical Friedel–Crafts Alkylation—A Sustainable Pathway Towards Porous Organic Polymers
Author(s) -
Troschke Erik,
Grätz Sven,
Lübken Tilo,
Borchardt Lars
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201702303
Subject(s) - friedel–crafts reaction , monomer , polymer , porosity , polymerization , triazine , materials science , cyanuric chloride , chemical engineering , alkylation , x ray photoelectron spectroscopy , polymer chemistry , chemistry , organic chemistry , catalysis , engineering
This study elucidates an innovative mechanochemical approach applying Friedel–Crafts alkylation to synthesize porous covalent triazine frameworks (CTFs). Herein, we pursue a counterintuitive approach by utilizing a rather destructive method to synthesize well‐defined materials with intrinsic porosity. Investigating a model system including carbazole as monomer and cyanuric chloride as triazine node, ball milling is shown to successfully yield porous polymers almost quantitatively. We verified the successful structure formation by an in‐depth investigation applying XPS, solid‐state NMR and FT‐IR spectroscopy. An in situ study of pressure and temperature developments inside the milling chamber in combination with two‐dimensional liquid‐state NMR spectroscopy reveals insights into the polymerization mechanism. The versatility of this mechanochemical approach is showcased by application of other monomers with different size and geometry.