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Switchable Aromaticity of Phthalocyanine via Reversible Nucleophilic Aromatic Addition to an Electron-Deficient Phosphorus(V) Complex
Reversible nucleophilic addition to a phthalocyanine core was observed for the first time for the electron-deficient cationic phosphorus(V) complex [PcP(OMe)2] + , whose reaction with KOH afforded a highly distorted nonaromatic adduct bearing an OH group at one of the α-pyrrolic carbon atoms. This...
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| Published in: | Journal of the American Chemical Society 2021-09, Vol.143 (35), p.14053-14058 |
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| Main Authors: | , , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-a390t-6309b33c475b0a36b2eda6245e4bf9f2fa5b7c09de70933f43e0b772a5ec31883 |
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| cites | cdi_FETCH-LOGICAL-a390t-6309b33c475b0a36b2eda6245e4bf9f2fa5b7c09de70933f43e0b772a5ec31883 |
| container_end_page | 14058 |
| container_issue | 35 |
| container_start_page | 14053 |
| container_title | Journal of the American Chemical Society |
| container_volume | 143 |
| creator | Kolomeychuk, Filipp M Safonova, Evgeniya A Polovkova, Marina A Sinelshchikova, Anna A Martynov, Alexander G Shokurov, Alexander V Kirakosyan, Gayane A Efimov, Nikolay N Tsivadze, Aslan Yu Gorbunova, Yulia G |
| description | Reversible nucleophilic addition to a phthalocyanine core was observed for the first time for the electron-deficient cationic phosphorus(V) complex [PcP(OMe)2] + , whose reaction with KOH afforded a highly distorted nonaromatic adduct bearing an OH group at one of the α-pyrrolic carbon atoms. This adduct was characterized by single-crystal X-ray diffraction, ESI HRMS, and NMR, and UV–vis spectroscopy, together with quantum-chemical modeling. The acidic treatment of this adduct restored aromaticity and recovered the starting cationic complex. The reversible aromaticity breakage resulted in dramatic changes in the photophysical properties of the studied complex, which could pave the way to novel switchable Pc-based compounds and materials. |
| doi_str_mv | 10.1021/jacs.1c05831 |
| format | article |
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| source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
| title | Switchable Aromaticity of Phthalocyanine via Reversible Nucleophilic Aromatic Addition to an Electron-Deficient Phosphorus(V) Complex |
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