Synthesis and molecular structure of perhalogenated rhenium-oxo corroles

Alemayehu, Abraham B.; Einrem, Rune F.; McCormick-McPherson, Laura J.; Settineri, Nicholas S.; Ghosh, Abhik

doi:10.1038/s41598-020-76308-7

Synthesis and molecular structure of perhalogenated rhenium-oxo corroles

Journal Article · Wed Nov 11 23:00:00 EST 2020 · Scientific Reports

DOI:https://doi.org/10.1038/s41598-020-76308-7· OSTI ID:1902580

Alemayehu, Abraham B.; Einrem, Rune F.; McCormick-McPherson, Laura J.; Settineri, Nicholas S.; Ghosh, Abhik

Abstract

As part of our efforts to develop rhenium-oxo corroles as photosensitizers for oxygen sensing and photodynamic therapy, we investigated the potential β -perhalogenation of five ReO meso -tris( para -X-phenyl)corroles, Re[T p XPC](O) (X = CF ₃ , H, F, CH ₃ , and OCH ₃ ), with elemental chlorine and bromine. With Cl ₂ , β -octachlorinated products Re[Cl ₈ T p XPC](O) were rapidly obtained for X = CF ₃ , H, and CH ₃ , but X = OCH ₃ resulted in overchlorination on the meso -aryl groups. Full β -octabromination proved slower relative to Cu and Ir corroles, but the desired Re[Br ₈ T p XPC](O) products were finally obtained for X = H and F after a week at room temperature. For X = CH ₃ and OCH ₃ , these conditions led to undecabrominated products Re[Br ₁₁ T p XPC](O). Compared to the β -unsubstituted starting materials, the β -octahalogenated products were found to exhibit sharp ¹ H NMR signals at room temperature, indicating that the aryl groups are locked in place by the β -halogens, and substantially redshifted Soret and Q bands. Single-crystal X-ray structures of Re[Cl ₈ T p CF ₃ PC](O), Re[Cl ₈ T p CH ₃ PC](O), and Re[Br ₈ T p FPC](O) revealed mild saddling for one Cl ₈ structure and the Br ₈ structure. These structural variations, however, appear too insignificant to explain the slowness of the β -octabromination protocols, which seems best attributed to the deactivating influence of the high-valent Re center.

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Sponsoring Organization:: USDOE

Grant/Contract Number:: AC02-05CH11231

OSTI ID:: 1902580

Alternate ID(s):: OSTI ID: 1763677

Journal Information:: Scientific Reports, Journal Name: Scientific Reports Journal Issue: 1 Vol. 10; ISSN 2045-2322

Publisher:: Nature Publishing GroupCopyright Statement

Country of Publication:: United Kingdom

Language:: English

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