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, 2024, 63 (30)
doi: 10.26083/tuprints-00028298
Artikel, Zweitveröffentlichung, Verlagsversion

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:	Zweitveröffentlichung
Titel:	Mechanochemical Cyclotrimerization: A Versatile Tool to Covalent Organic Frameworks with Tunable Stacking Mode
Sprache:	Englisch
Publikationsjahr:	5 November 2024
Ort:	Darmstadt
Publikationsdatum der Erstveröffentlichung:	22 Juli 2024
Ort der Erstveröffentlichung:	Weinheim
Verlag:	Wiley-VCH
Titel der Zeitschrift, Zeitung oder Schriftenreihe:	Angewandte Chemie International Edition
Jahrgang/Volume einer Zeitschrift:	63
(Heft-)Nummer:	30
Kollation:	7 Seiten
DOI:	10.26083/tuprints-00028298
URL / URN:	https://tuprints.ulb.tu-darmstadt.de/28298
Zugehörige Links:	Supplements Verlags-DOI
Herkunft:	Zweitveröffentlichung DeepGreen
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.
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
Status:	Verlagsversion
URN:	urn:nbn:de:tuda-tuprints-282983
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:	05 Nov 2024 13:07
Letzte Änderung:	06 Nov 2024 09:25
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Verfügbare Versionen dieses Eintrags

• Mechanochemical Cyclotrimerization: A Versatile Tool to Covalent Organic Frameworks with Tunable Stacking Mode. (deposited 05 Nov 2024 13:07) [Gegenwärtig angezeigt]
  • Mechanochemical cyclotrimerization: a versatile tool to covalent organic frameworks with tunable stacking mode. (deposited 06 Nov 2024 09:26)

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