Expanding the boron peroxide chemistry on BODIPY scaffold

Prinčič, Griša Grigorij (author), Lozinšek, Matic (author), Iskra, Jernej (author)

Novel stable BODIPY boron mono- and diperoxides were prepared in good yields by TMSOTf activation of mono- and dialkoxy-BODIPY derivatives, followed by ligand exchange with organic hydroperoxides. The reactions of the methoxy derivative of BODIPY with hydroperoxides led to the formation of a novel group of peroxides with the structural element B(F)OOR. The reaction of the dimethoxy derivative of BODIPY with $^t$BuOOH provided the first organic boron diperoxide. Using gem-dihydroperoxide, a cyclic analogue with tetraoxaborinane ring was prepared. Both, mono- and diperoxo boron compounds are stable under ambient conditions, which allowed full characterization of compounds. A mechanistic study provided further insight into their formation and elucidated some of the possible intermediates, namely the borenium cations.

• Language: English
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2021
• Number of pages: 8 str.
• Numbering: Vol. 190, art. 109290
• PID: 20.500.12556/RUL-138672
• UDC: 54
• ISSN on article: 0143-7208
• DOI: 10.1016/j.dyepig.2021.109290
• COBISS.SI-ID: 54876419
• Publication date in RUL: 09.08.2022

Record is a part of a journal

• Title: Dyes and pigments
• Shortened title: Dyes pigm.
• Publisher: Elsevier
• ISSN: 0143-7208
• COBISS.SI-ID: 25357056

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• Link: http://creativecommons.org/licenses/by-nc-nd/4.0/
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