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Copper(III) organometallic complexes of non (anti)aromatic and aromatic doubly N-confused porphyrinoids: syntheses and characterization

The retrosynthetic design and synthesis of three unprecedented doubly N-confused porphyrinoids with tunable aromaticity are reported. The controlled modification of the type of oxidant (chloranil vs. DDQ) led to the isolation of cross-conjugated doubly N-confused porphyrinoid 7 (upon chloranil oxida...

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Main Authors: Panua, Anirban (Author) , Velmurugan, Gunasekaran (Author) , Comba, Peter (Author) , Rath, Harapriya (Author)
Format: Article (Journal)
Language:English
Published: 27 Jan 2025
In: Dalton transactions
Year: 2025, Volume: 54, Issue: 10, Pages: 4267-4275
ISSN:1477-9234
DOI:10.1039/D4DT03265A
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1039/D4DT03265A
Verlag, lizenzpflichtig, Volltext: https://pubs.rsc.org/en/content/articlelanding/2025/dt/d4dt03265a
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Author Notes:Anirban Panua, Gunasekaran Velmurugan, Peter Comba and Harapriya Rath
Description
Summary:The retrosynthetic design and synthesis of three unprecedented doubly N-confused porphyrinoids with tunable aromaticity are reported. The controlled modification of the type of oxidant (chloranil vs. DDQ) led to the isolation of cross-conjugated doubly N-confused porphyrinoid 7 (upon chloranil oxidation) and Hϋckel aromatic porphyrinoid 8, while DDQ oxidation led to the [16]π Hϋckel-antiaromatic porphyrinoid 9. All three hybrid N-confused porphyrinoids 7-9 have been thoroughly characterized via solution-state spectroscopic measurements and in-depth DFT studies. While 7 and 8 could form respective Cu(III) organometallic complexes, porphyrinoid 9 remained unsusceptible to Cu metallation.
Item Description:Gesehen am 25.07.2025
Physical Description:Online Resource
ISSN:1477-9234
DOI:10.1039/D4DT03265A

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