A novel complex of zinc tetraphenylporphyrin with two dioxane molecules in a rare attachment. Crystal structure, spectroscopy and theoretical calculations

Oberda, Krzysztof; Deperasińska, Irena; Nizhnik, Yakov P.; Szemik-Hojniak, Anna

doi:10.1016/j.poly.2012.12.014

Cited by 16 publications

(13 citation statements)

References 45 publications

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“…1.6 ns (except 2 , which has a smaller τ f value of 1.3 ns). Therefore, the lifetimes of the zinc metalloporphyrins do not depend on the axial ligand, as was also shown for the related species [Zn(TPP)(IQNO)] (IQNO = isoquinoline N ‐oxide) and [Zn(TPP)(1,4‐dioxane) 2 ] …”

Section: Resultssupporting

confidence: 59%

“…An understanding of the effects of axial ligands and the nature of the peripheral groups of the porphyrin core of zinc metalloporphyrins on the electronic, redox, structural, photophysical, and other physical properties is very important for the use of these species in the different applications mentioned above. In this context, a significant number of investigations have been performed on the synthesis and characterization of new porphyrins with different substituents at the porphyrin core with different donor and acceptor properties as well as steric characters …”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Electronic Spectroscopy, Cyclic Voltammetry, Photophysics, Electrical Properties and X‐ray Molecular Structures of meso‐{Tetrakis[4‐(benzoyloxy)phenyl]porphyrinato}zinc(II) Complexes with Aza Ligands

et al. 2016

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The synthesis of the new meso-porphyrin tetrakis-[4-(benzoyloxy)phenyl]porphyrin (H 2 TPBP), the meso-{tetrakis-[4-(benzoyloxy)phenyl]porphyrinato}zinc(II) starting material [Zn(TPBP)] (1), and the 1,4-diazabicyclo[2.2.2]octane (dabco), pyrazine (pyz), 4,4′-bipyridine (4,4′-bpy), 4,4′-diaminodiphenylmethane (4,4′-mda), and 4-cyanopyridine (4-CNpy) coordination compounds with [Zn(TPBP)] (2-7) are described. The preparation of the dabco derivative in chlorobenzene leads to a crystalline monomeric five-coordinate zinc porphyrin species (2), whereas the synthesis in dichloromethane gives a five-coordinate zinc metalloporphyrin dimer (3) in the solid state. The pyrazine derivative crystallizes as a bis-pyrazine six-coordinate zinc metalloporphyrin (4). Complex 5 in the solid state is a dimer with 4,4′-bpy as a bridging ligand, whereas the 4,4′-mda species (6) is a five-coordinated monomeric zinc derivative in [a] 5004 Scheme 1. Schematic representations of the different coordination types for zinc porphyrins with bidentate N-donor ligands (L). Scheme 2. Bidentate N-donor ligands (aza ligands) used in this work.

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Section: Resultssupporting

confidence: 59%

Section: Introductionmentioning

confidence: 99%

Synthesis, Electronic Spectroscopy, Cyclic Voltammetry, Photophysics, Electrical Properties and X‐ray Molecular Structures of meso‐{Tetrakis[4‐(benzoyloxy)phenyl]porphyrinato}zinc(II) Complexes with Aza Ligands

et al. 2016

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“…9 ns) are much higher than those of [Zn(TPP)] and [Zn(TTP)] (1.9 and 1.6 ns, respectively). In addition, τ f is not influenced by the presence of the axial ligand, and the τ f value for 1 – 4 (1.7 ns) is close to those for [Zn(TPP)], [Zn(TTP)], [Zn(TPP)(1,4‐dioxane) 2 ] (1.75 ns),31 and [Zn(TPP)(IQNO)] (1.92 ns) 30. A comparison of the photophysical properties of the zinc derivatives 1 – 4 with those of the related magnesium species [Mg(TPP)(X)] – (X = N 3 – , NCO – , NCS – ) leads to the same observation already postulated by Ghosh et al32 Thus, the magnesium porphyrins21 exhibit higher fluorescence quantum yields (0.10 ≤ Φ f ≤ 0.16) and longer excited‐state lifetimes (4–9 ns) compared with those of the zinc porphyrins.…”

Section: Resultssupporting

confidence: 55%

Insights on the UV/Vis, Fluorescence, and Cyclic Voltammetry Properties and the Molecular Structures of Zn^II Tetraphenylporphyrin Complexes with Pseudohalide Axial Azido, Cyanato‐N, Thiocyanato‐N, and Cyanido Ligands

et al. 2015

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The syntheses, spectroscopic and photophysical properties, and molecular structures of azido-(1), cyanato-N-(2), thio cyanato-N-(3), and cyanido-(4) (meso-tetraphenylporphyrinato)zinc(II) complexes are reported. These species were prepared by using cryptand-222 to solubilize the pseudohalide salts in organic solvents. The UV/Vis spectra of these zinc metalloporphyrins are solvent-dependent and exhibit large redshifted Soret bands compared with those of the [Zn(Porph)L] derivatives in which Porph is a meso-porphyrinato ligand and L is a monodentate neutral axial ligand. The room-temperature fluorescence spectra of the zinc complexes 1-4 indicate that the Q bands are not very affected by the nature of the axial ligands, and their positions are very close to those of previously reported (meso-porphyrinato)zinc complexes. The quantum yields of the S 1 Ǟ S o fluorescence of 1-4 range between 2.8 and 5.5 %, and their fluorescence lifetimes are the same (1.7 ns). Cyclic voltammetry investigations on 1-4 show that the characteristic potentials for the reduction and the two first oxidations of the porphyrin ring 2596are not very affected by the nature of the axial ligand. A third irreversible oxidation of the porphyrin ring is observed. Additional anodic irreversible waves are observed for the thiocyanato-N (3) and cyanido (4) species. The solid-state molecular structures of 1-4 are the first examples of zinc porphyrin complexes with anionic ligands. The average equatorial zinc-pyrrole N atom (Zn-N p ) distances for 1-4 range between 2.083(1) and 2.117(2) Å and are much longer than those of the related pentacoordinate zinc porphyrin complexes with monodentate neutral ligands. As a consequence, the displacement of the Zn 2+ cation from the mean 24-atom plan of the porphyrin core is significant (ca. 0.5 Å), and the porphyrin core is very distorted. The crystal structures of 1-4 are stabilized by weak intermolecular π interactions, CH···Cg (Cg are the centroids of some six-membered phenyl rings and five-membered pyrrole rings). The molecular structure of 1 is further stabilized by weak intermolecular C-H···N hydrogen bonds between one carbon atom of cryptand-222 and the terminal nitrogen atom of the azido ligand.

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“…16 It is noteworthy that even though the Zn 2+ ion in the porphyrin center has a marked preference for vecoordinate square-pyramidal geometry, few examples of sixcoordinated zinc porphyrin complexes are known in solution. 17,18 Several investigations involving zinc porphyrins with aza ligands have been reported. [19][20][21][22][23] These studies concern bis(zincporphyrin) tweezers and were aimed to design and study the photoactive multicomponent systems which lead to the understanding of the bacterial photosynthesis.…”

Section: Introductionmentioning

confidence: 99%

Tetrakis(ethyl-4(4-butyryl)oxyphenyl)porphyrinato zinc complexes with 4,4′-bpyridin: synthesis, characterization, and its catalytic degradation of Calmagite

et al. 2018

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A novel complex of zinc tetraphenylporphyrin with two dioxane molecules in a rare attachment. Crystal structure, spectroscopy and theoretical calculations

Cited by 16 publications

References 45 publications

Synthesis, Electronic Spectroscopy, Cyclic Voltammetry, Photophysics, Electrical Properties and X‐ray Molecular Structures of meso‐{Tetrakis[4‐(benzoyloxy)phenyl]porphyrinato}zinc(II) Complexes with Aza Ligands

Synthesis, Electronic Spectroscopy, Cyclic Voltammetry, Photophysics, Electrical Properties and X‐ray Molecular Structures of meso‐{Tetrakis[4‐(benzoyloxy)phenyl]porphyrinato}zinc(II) Complexes with Aza Ligands

Insights on the UV/Vis, Fluorescence, and Cyclic Voltammetry Properties and the Molecular Structures of Zn^II Tetraphenylporphyrin Complexes with Pseudohalide Axial Azido, Cyanato‐N, Thiocyanato‐N, and Cyanido Ligands

Tetrakis(ethyl-4(4-butyryl)oxyphenyl)porphyrinato zinc complexes with 4,4′-bpyridin: synthesis, characterization, and its catalytic degradation of Calmagite

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A novel complex of zinc tetraphenylporphyrin with two dioxane molecules in a rare attachment. Crystal structure, spectroscopy and theoretical calculations

Cited by 16 publications

References 45 publications

Synthesis, Electronic Spectroscopy, Cyclic Voltammetry, Photophysics, Electrical Properties and X‐ray Molecular Structures of meso‐{Tetrakis[4‐(benzoyloxy)phenyl]porphyrinato}zinc(II) Complexes with Aza Ligands

Synthesis, Electronic Spectroscopy, Cyclic Voltammetry, Photophysics, Electrical Properties and X‐ray Molecular Structures of meso‐{Tetrakis[4‐(benzoyloxy)phenyl]porphyrinato}zinc(II) Complexes with Aza Ligands

Insights on the UV/Vis, Fluorescence, and Cyclic Voltammetry Properties and the Molecular Structures of ZnII Tetraphenylporphyrin Complexes with Pseudohalide Axial Azido, Cyanato‐N, Thiocyanato‐N, and Cyanido Ligands

Tetrakis(ethyl-4(4-butyryl)oxyphenyl)porphyrinato zinc complexes with 4,4′-bpyridin: synthesis, characterization, and its catalytic degradation of Calmagite

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Insights on the UV/Vis, Fluorescence, and Cyclic Voltammetry Properties and the Molecular Structures of Zn^II Tetraphenylporphyrin Complexes with Pseudohalide Axial Azido, Cyanato‐N, Thiocyanato‐N, and Cyanido Ligands