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The mechanochemical Friedel‐Crafts polymerization as a solvent‐free cross‐linking approach toward microporous polymers

Krusenbaum, Annika ; Geisler, Jonathan ; Kraus, Fabien Joel Leon ; Grätz, Sven ; Höfler, Mark Valentin ; Gutmann, Torsten ; Borchardt, Lars (2022):
The mechanochemical Friedel‐Crafts polymerization as a solvent‐free cross‐linking approach toward microporous polymers. (Publisher's Version)
In: Journal of Polymer Science, 60 (1), pp. 62-71. John Wiley & Sons, e-ISSN 2642-4169,
DOI: 10.26083/tuprints-00021005,
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Item Type: Article
Origin: Secondary publication DeepGreen
Status: Publisher's Version
Title: The mechanochemical Friedel‐Crafts polymerization as a solvent‐free cross‐linking approach toward microporous polymers
Language: English
Abstract:

Herein we report the mechanochemical Friedel‐Crafts alkylation of 1,3,5‐triphenylbenzene (TPB) with two organochloride cross‐linking agents, dichloromethane (DCM) and chloroform (CHCl₃), respectively. During a thorough milling parameter evaluation, the DCM‐linked polymers were found to be flexible and extremely sensitive toward parameter changes, which even enables the synthesis of a polymer with a SSABET of 1670 m²/g, on par with the solution‐based reference. Contrary, CHCl₃‐linked polymers are exhibiting a rigid structure, with a high porosity that is widely unaffected by parameter changes. As a result, a polymer with a SSABET of 1280 m²/g could be generated in as little as 30 minutes, outperforming the reported literature analogue in terms of synthesis time and SSABET. To underline the environmental benefits of our fast and solvent‐free synthesis approach, the green metrics are discussed, revealing an enhancement of the mass intensity, mass productivity and the E‐factor, as well as of synthesis time and the work‐up in comparison to the classical synthesis. Therefore, the mechanochemical polymerization is presented as a versatile tool, enabling the generation of highly porous polymers within short reaction times, with a minimal use of chlorinated cross‐linker and with the possibility of a post polymerization modification.

Journal or Publication Title: Journal of Polymer Science
Volume of the journal: 60
Issue Number: 1
Place of Publication: Darmstadt
Publisher: John Wiley & Sons
Uncontrolled Keywords: cross‐linking, Friedel‐Crafts alkylation, high‐speed ball milling, mechanochemistry, microporous polymers
Classification DDC: 500 Naturwissenschaften und Mathematik > 540 Chemie
Divisions: 07 Department of Chemistry > Fachgebiet Anorganische Chemie
Date Deposited: 08 Jul 2022 11:23
Last Modified: 08 Sep 2022 09:02
DOI: 10.26083/tuprints-00021005
Corresponding Links:
URN: urn:nbn:de:tuda-tuprints-210057
SWORD Depositor: Deep Green
URI: https://tuprints.ulb.tu-darmstadt.de/id/eprint/21005
PPN: 498979326
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