Mechanochemical cyclotrimerization: a versatile tool to covalent organic frameworks with tunable stacking mode

Hutsch, Stefanie ; Leonard, Allison ; Grätz, Sven ; Höfler, Mark Valentin ; Gutmann, Torsten ; Borchardt, Lars (2024)
Mechanochemical cyclotrimerization: a versatile tool to covalent organic frameworks with tunable stacking mode.
In: Angewandte Chemie International Edition, 63 (30)
doi: 10.1002/anie.202403649
Artikel, Bibliographie

Dies ist die neueste Version dieses Eintrags.

Kurzbeschreibung (Abstract)

We introduce the first mechanochemical cyclotrimerization of nitriles, a facile strategy for synthesizing triazine‐containing molecules and materials, overcoming challenges related to carbonization and solubility. Conducting this solid‐state approach in a mixer ball mill with 4‐Methylbenzonitrile, we synthesize Tris(4‐methylphenyl)‐1,3,5‐triazine quantitatively in as little as 90 minutes. Just as fast, this mechanochemical method facilitates the synthesis of the covalent triazine framework CTF‐1 using 1,4 Dicyanobenzene. Material characterization confirms its porous (650 m² g⁻¹) and crystalline nature. Adjusting the induced mechanical energy allows control over the obtained stacking conformation of the resulting CTFs ‐ from a staggered AB arrangement to an eclipsed AA stacking conformation. Finally, a substrate scope demonstrates the versatility of this approach, successfully yielding various CTFs.

Typ des Eintrags:

Artikel

Erschienen:

2024

Autor(en):

Hutsch, Stefanie ; Leonard, Allison ; Grätz, Sven ; Höfler, Mark Valentin ; Gutmann, Torsten ; Borchardt, Lars

Art des Eintrags:

Bibliographie

Titel:

Mechanochemical cyclotrimerization: a versatile tool to covalent organic frameworks with tunable stacking mode

Sprache:

Englisch

Publikationsjahr:

22 Juli 2024

Ort:

Weinheim

Verlag:

Wiley-VCH

Titel der Zeitschrift, Zeitung oder Schriftenreihe:

Angewandte Chemie International Edition

Jahrgang/Volume einer Zeitschrift:

(Heft-)Nummer:

Kollation:

7 Seiten

DOI:

10.1002/anie.202403649

Zugehörige Links:

Kurzbeschreibung (Abstract):

Alternatives oder übersetztes Abstract:

Alternatives Abstract

Sprache

This work presents, for the first time, the mechanochemical cyclotrimerization of nitriles. Utilizing Trifluoromethanesulfonic acid and a ball mill, both small molecules and large organic frameworks could be obtained. Screening the reaction of 1,4-Dicyanobenzene by various parameters, such as reaction time, frequency, or temperature, significant impacts on the porosity of the polymer and its crystallinity were revealed.

Englisch

Freie Schlagworte:

cyclotrimerization, mechanochemistry, covalent triazine framework, NMR spectroscopy

ID-Nummer:

Artikel-ID: e202403649

Zusätzliche Informationen:

This article also appears in: Hot Topic: Mechanochemistry

Sachgruppe der Dewey Dezimalklassifikatin (DDC):

500 Naturwissenschaften und Mathematik > 530 Physik
500 Naturwissenschaften und Mathematik > 540 Chemie

Fachbereich(e)/-gebiet(e):

07 Fachbereich Chemie
07 Fachbereich Chemie > Eduard Zintl-Institut
07 Fachbereich Chemie > Eduard Zintl-Institut > Fachgebiet Physikalische Chemie

Hinterlegungsdatum: