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Insights into the mechanism of energy transfer with poly(heptazine imide)s in deoximation reaction

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Galushchinskiy,  Alexey
Aleksandr Savateev, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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ten Brummelhuis,  Katharina
Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Antonietti,  Markus
Markus Antonietti, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Savateev,  Aleksandr
Aleksandr Savateev, Kolloidchemie, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Galushchinskiy, A., ten Brummelhuis, K., Antonietti, M., & Savateev, A. (2021). Insights into the mechanism of energy transfer with poly(heptazine imide)s in deoximation reaction. ChemPhotoChem, 5(11), 1020-1025. doi:10.1002/cptc.202100088.


Cite as: http://hdl.handle.net/21.11116/0000-0008-EE1F-B
Abstract
Following our previous studies on potassium poly(heptazine imide) (K-PHI) – catalyzed photooxidative [3+2] aldoxime-to-nitrile addition to form 1,2,4-oxadiazoles, we discovered that electron-rich oximes yield the parent aldehydes instead of target products. In this work, the mechanism of this singlet oxygen-mediated deoximation process was established using a series of control reactions and spectroscopic measurements such as steady-state and time-resolved fluorescence quenching experiments. Additionally, singlet-triplet energy gap value was obtained for K-PHI in suspension, and the reaction scope was broadened to include ketoximes.