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Synthesis, Protonation and Aromatic Characteristics of a Series of 1,10-Phenanthroline-Fused Porphyrinoids.
J Org Chem
January 2025
Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, United States.
A series of porphyrin analogues with fused 1,10-phenanthroline units were synthesized. The proton NMR spectra for phenanthroline-fused heteroporphyrins showed significantly upfield shifted -proton resonances compared to related porphyrinoid systems and the peaks corresponding to alkyl substituents directly attached to these macrocycles were also observed further upfield. These results indicate that the presence of the phenanthroline unit leads to reduced diatropicity, but the internal NH resonance was also further upfield, a result that is inconsistent with this interpretation.
View Article and Find Full Text PDFSubstitution-pattern- and counteranion-dependent ion-pairing assemblies of heteroporphyrin-based π-electronic cations.
Chem Commun (Camb)
April 2024
Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu 525-8577, Japan.
Metal complexation and peripheral modifications of thiaporphyrins have been investigated for preparing polarized π-electronic cations with anion-dependent ion-pairing assembling modes, including charge-segregated structures exhibiting electric conductive properties.
View Article and Find Full Text PDFChalcogen atom effect on the intersystem crossing kinetic constant of oxygen- and sulfur disubstituted heteroporphyrins.
J Comput Chem
June 2024
Dipartimento di Chimica e Tecnologie Chimiche, Università della Calabria, Rende, Italy.
The modulation of the photophysical properties of di-substituted porphyrin rings upon the oxygen and sulfur-for-nitrogen replacement has been investigated at density functional theory (DFT) and its time-dependent formulation (TDDFT). The considered properties range from structural behaviors and excitation energies to spin-orbit coupling (SOC) and nonradiative intersystem kinetic constants. Results show that the SOC strongly increase upon chalcogen substitution and, accordingly, the computed nonradiative kinetic constant also indicate an efficient singlet-triplet intersystem crossing in the sulfur containing macrocycle.
View Article and Find Full Text PDFSynthesis of Phenothiazine Embedded Heteroporphyrins.
Chem Asian J
January 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India .
A series of phenothiazine embedded heteroporphyrins containing one phenothiazine unit, two pyrrole rings and one heterocycle such as furan, thiophene, selenophene and tellurophene connected via four meso carbons were synthesized. The macrocycles were synthesized by condensing the phenothiazine based tripyrrane with corresponding 2,5-bis(hydroxymethyl)heterocycle under BF ⋅ OEt catalyzed conditions and compared the structural, spectral, and electrochemical properties with the reported phenothiazinophyrins. The studies showed that the phenothiazine embedded heteroporphyrins were nonaromatic and electronic properties were significantly altered by replacing the pyrrole ring from phenothiazinophyrin with different heterocycles.
View Article and Find Full Text PDFIon-pairing assemblies of heteroporphyrin-based π-electronic cation with various counteranions.
Chem Commun (Camb)
September 2022
Department of Applied Chemistry, College of Life Sciences, Ritsumeikan University, Kusatsu, 525-8577, Japan.
Various counteranions of the thiaporphyrin-Ni complex as a π-electronic cation were exchanged for preparing stable ion pairs. The ion-pairing assembling modes, which included contributions of charge-by-charge and charge-segregated modes, and properties depended on the geometries and electronic states of the counteranions.
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