Mechanochemically Assisted Synthesis of Hexaazatriphenylenehexacarbonitrile

[Image: see text] 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (HAT CN) was synthesized mechanochemically at room temperature. The coupling of hexaketocyclohexane and diaminomaleonitrile was conducted in 10 min by vibratory ball milling. The effects of milling parameters, acids, dehydrating agen...

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Autores principales: Pickhardt, Wilm, Wohlgemuth, Maximilian, Grätz, Sven, Borchardt, Lars
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8524413/
https://www.ncbi.nlm.nih.gov/pubmed/34014673
http://dx.doi.org/10.1021/acs.joc.1c00253
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author Pickhardt, Wilm
Wohlgemuth, Maximilian
Grätz, Sven
Borchardt, Lars
author_facet Pickhardt, Wilm
Wohlgemuth, Maximilian
Grätz, Sven
Borchardt, Lars
author_sort Pickhardt, Wilm
collection PubMed
description [Image: see text] 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (HAT CN) was synthesized mechanochemically at room temperature. The coupling of hexaketocyclohexane and diaminomaleonitrile was conducted in 10 min by vibratory ball milling. The effects of milling parameters, acids, dehydrating agents, and liquid-assisted grinding were rationalized. With 67%, the yield of this mechanochemical approach exceeds that of state-of-the-art wet-chemical syntheses while being superior with respect to time-, resource-, and energy-efficiency as quantified via green metrics.
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spelling pubmed-85244132021-10-19 Mechanochemically Assisted Synthesis of Hexaazatriphenylenehexacarbonitrile Pickhardt, Wilm Wohlgemuth, Maximilian Grätz, Sven Borchardt, Lars J Org Chem [Image: see text] 1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (HAT CN) was synthesized mechanochemically at room temperature. The coupling of hexaketocyclohexane and diaminomaleonitrile was conducted in 10 min by vibratory ball milling. The effects of milling parameters, acids, dehydrating agents, and liquid-assisted grinding were rationalized. With 67%, the yield of this mechanochemical approach exceeds that of state-of-the-art wet-chemical syntheses while being superior with respect to time-, resource-, and energy-efficiency as quantified via green metrics. American Chemical Society 2021-05-20 2021-10-15 /pmc/articles/PMC8524413/ /pubmed/34014673 http://dx.doi.org/10.1021/acs.joc.1c00253 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Pickhardt, Wilm
Wohlgemuth, Maximilian
Grätz, Sven
Borchardt, Lars
Mechanochemically Assisted Synthesis of Hexaazatriphenylenehexacarbonitrile
title Mechanochemically Assisted Synthesis of Hexaazatriphenylenehexacarbonitrile
title_full Mechanochemically Assisted Synthesis of Hexaazatriphenylenehexacarbonitrile
title_fullStr Mechanochemically Assisted Synthesis of Hexaazatriphenylenehexacarbonitrile
title_full_unstemmed Mechanochemically Assisted Synthesis of Hexaazatriphenylenehexacarbonitrile
title_short Mechanochemically Assisted Synthesis of Hexaazatriphenylenehexacarbonitrile
title_sort mechanochemically assisted synthesis of hexaazatriphenylenehexacarbonitrile
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8524413/
https://www.ncbi.nlm.nih.gov/pubmed/34014673
http://dx.doi.org/10.1021/acs.joc.1c00253
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