Controlled distortion of planar porphyrin by intramolecular N-alkylation
The distortion of aromatic macrocycle is of significant interest for understanding of the π-conjugated system. Herein, porphyrin rings with different distortions were synthesized due to intramolecular N-alkylation by introducing a tetraethylene glycol chain. After binding of the cross-linking group...
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| Autores principales: | , , , , , , |
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| Formato: | article |
| Lenguaje: | EN |
| Publicado: |
Elsevier
2021
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| Materias: | |
| Acceso en línea: | https://doaj.org/article/f0c2988104e44166a0ad44e2310fa9cd |
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| Sumario: | The distortion of aromatic macrocycle is of significant interest for understanding of the π-conjugated system. Herein, porphyrin rings with different distortions were synthesized due to intramolecular N-alkylation by introducing a tetraethylene glycol chain. After binding of the cross-linking group of tetraethylene glycol chain to the porphyrin phenyl group, intramolecular cyclization using silver tetrafluoroborate afforded two types of intramolecularly cross-linked N-substituted porphyrins that were alkylated at the N21, (22) or N23, (24) positions. We found that intramolecularly cross-linked N-substituted porphyrins in which the pyrrole nitrogen was connected by a tetraethylene glycol chain afforded different distortions of the porphyrin ring depending on the N-alkylated substitution position. |
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