Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
Review
. 2021 Nov;97(6):1278-1288.
doi: 10.1111/php.13403. Epub 2021 Mar 8.

Photochemistry of Tris(2,4-dibromophenyl)amine and its Application to Co-oxidation on Sulfides and Phosphines

Sergio M Bonesi  1   2   3 , Mariella Mella  4 , Daniele Merli  4 , Stefano Protti  3
Affiliations
Review

Photochemistry of Tris(2,4-dibromophenyl)amine and its Application to Co-oxidation on Sulfides and Phosphines

Sergio M Bonesi et al. Photochem Photobiol. 2021 Nov.

Abstract

The photochemistry of tris(2,4-dibromophenyl)amine was investigated via time-resolved nanosecond spectroscopy. The tris(2,4-dibromophenyl)amine radical cation ("Magic Green") was immediately detected after the laser pulse; this intermediate then cyclizes to N-aryl-4a,4b-dihydrocarbazole radical cation. The latter transient reacted with molecular oxygen to provide the corresponding hydroperoxyl radical, which smoothly co-oxidize sulfides into sulfoxides. On the other hand, the photogenerated "Magic Green" was exploited to promote the co-oxidation of nucleophilic triarylphosphines to triarylphosphine oxides through an electron transfer process preventing the amine cyclization. In this case, the intermediate Ar3 POO•+ was found to play a key role in phosphine oxide formation.

PubMed Disclaimer

References

REFERENCES

    1. Seo, E. T., R. F. Nelson, J. M. Fritsch, L. S. Macoux, D. T. Leedy and R. N. Adams (1966) Anodic oxidation pathways of aromatic amines. Electrochemical and electron paramagnetic resonance studies. J. Am. Chem. Soc. 88, 3498-3503.
    1. Ambrose, J. F., L. L. Carpenter and R. F. Nelson (1975) Electrochemical and spectroscopic properties of cation radicals. III. Reaction pathways of carbazolium radical ions. J. Electrochem. Soc. 122, 876-894.
    1. Papouchado, L., R. N. Adams and S. W. Feldberg (1969) Anodic catalytic currents involving cyanide ion. J. Electroanal. Chem. Interfacial Electrochem. 21, 408-410.
    1. Odon, S. A., S. Ergun, P. P. Poudel and S. R. Parkin (2014) A fast, inexpensive method for predicting overcharge performance in lithium-ion batteries. Energy Environ. Sci. 7, 760-767.
    1. Valenti, G., C. Bruno, S. Rapino, A. Fiorani, E. A. Jackson, L. T. Scott, R. Paolucci and M. Marcaccio (2010) Intense and tunable electrochemiluminescence of corannulene. J. Phys. Chem. C. 114, 19467-19472.

LinkOut - more resources