A Stable Organic π‐Radical of a Zinc(II)–Copper(I)–Zinc(II) Complex of Decaphyrin

Tanaka, Yasuo; Yoneda, Tomohiro; Furukawa, Ko; Koide, Taro; Mori, Haruo; Tanaka, Takayuki; Shinokubo, Hiroshi; Osuka, Atsuhiro

doi:10.1002/ange.201505130

Cited by 17 publications

(11 citation statements)

References 43 publications

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“…Absorption spectra were measured with a JASCO UV/vis/NIR Spectrophotometer V-670. 1 H NMR and 19 F NMR spectra were recorded on a JNM-ECX 400 spectrometer (operating as 400 MHz for 1 H and 376 MHz for 19 F) using the residual solvent as the internal reference for 1 H (δ = 7.26 ppm in CDCl 3 , δ = 5.32 ppm in CD 2 Cl 2 , and δ = 5.95 ppm in C 2 D 2 Cl 4 ) and CF 3 COOH as the external reference for 19 F (δ = −76.5 ppm). HR-MALDI-TOF mass spectrum was recorded on a Bruker Daltonics autoflex MALDI-TOF MS spectrometer.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…3H-1: UV−vis−NIR (CH 2 Cl 2 ) λ [nm] (ε [M −1 cm −1 ]): 541 (1.9 × 10 5 ), 685 (1.1 × 10 4 ), 798 (2.6 × 10 3 ) and 991 nm (1.5 × 10 3 ). 1…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Hexaphyrins and further expanded porphyrins comprising six or more pyrrole rings are significant research targets owing to their large and flexible structures, optical and electrochemical properties, and diverse coordination abilities. 1 In 1997, Dolphin's group reported the first synthesis of meso-hexaphenylhexaphyrin (1.1.1.1.1.1) by [3 + 3] type condensation reaction. 2 Two years later, Cavaleiro's group reported the stable meso-hexakis(pentafluorophenyl)hexaphyrin (1.1.1.1.1.1) using the Rothemund method.…”

Section: ■ Introductionmentioning

confidence: 99%

“…5 Hexaphyrins and further expanded porphyrins have rich and specific coordination abilities, inducing unusual twisted structures and optical properties, such as Huckel/ Mobius aromaticities. Generally, hexaphyrins (1.1.1.1.1.1) form mono-or binuclear metal complexes 1,6 and more than two metal ions can be inserted into further expanded porphyrins. 7 In many cases, hexaphyrins involve one carbon at mesopositions between pyrrole units, but the number of mesocarbon atoms plays an important role in determining molecular structure and conformation.…”

Section: ■ Introductionmentioning

confidence: 99%

“…These electronic properties can be attributed to the aromatic properties of 3H-1, H 6 1 3+ , and 3Rh-1. 1 The redox properties of 3H-1 and 3Rh-1 were measured by cyclic voltammetry (CV) and differential pulse voltammetry (DPV) in dichloromethane with 0.1 M tetrabutylammonium hexafluorophosphate (TBAPF 6 ) as an electrolyte (Figure 4).…”

Section: ■ Introductionmentioning

confidence: 99%

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[30]Hexaphyrin(2.1.2.1.2.1) as Aromatic Planar Ligand and Its Trinuclear Rhodium(I) Complex

et al. 2018

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Expanded porphyrins are attractive research targets because of their large and flexible structures, optical and electrochemical properties, and diverse coordination abilities. We are interested in the use of double bonds within expanded porphyrins because double bonds could conduct isomerization, expansion of π-conjugation, and giving different molecular geometry. We, thus, report [30]hexaphyrin(2.1.2.1.2.1) 3H-1, which was synthesized by a simple condensation reaction of 1,2-di(pyrrol-2-yl)ethene and pentafluorobenzaldehyde under an acidic condition. The compound 3H-1 exhibited 30π aromatic property with a highly planar structure, displaying intense Soret- and weak Q-like absorption bands. The compound 3H-1 has a sufficient space and dipyrrin-like coordination sites in its cavity. Trinuclear rhodium(I) complex 3Rh-1 was obtained with [Rh(CO)Cl] and exhibited six redox potentials.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

“…3H-1: UV−vis−NIR (CH 2 Cl 2 ) λ [nm] (ε [M −1 cm −1 ]): 541 (1.9 × 10 5 ), 685 (1.1 × 10 4 ), 798 (2.6 × 10 3 ) and 991 nm (1.5 × 10 3 ). 1…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

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[30]Hexaphyrin(2.1.2.1.2.1) as Aromatic Planar Ligand and Its Trinuclear Rhodium(I) Complex

et al. 2018

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Triggering Redox Activity in a Thiophene Compound: Radical Stabilization and Coordination Chemistry

et al. 2017

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The synthesis,metalation, and redoxproperties of an acyclic bis(iminothienyl)methene L À are presented. This pconjugated anion displayed pronounced redoxactivity,undergoing facile one-electron oxidation to the acyclic,m etal-free, neutral radical LC on reaction with FeBr 2 .I nc ontrast, the reaction of L À with CuI formed the unique,n eutral Cu 2 I 2 (LC) complex of aligand-centered radical, whereas reaction with the stronger oxidant AgBF 4 formed the metal-free radical dication LC 2+ .Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Synthesis of (bis)Silicon Complexes of [38], [37], and [36]Octaphyrins: Aromaticity Switch and Stable Radical Cation

et al. 2018

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Silicon complexation of a[ 38]octaphyrin (1)w as accomplished by reaction with an excess amount of MeSiCl 3 in the presence of N,N-diisopropylethylamine,t hus giving an aromatic [38]octaphyrin bis(silicon) complex 2.This complex was interconvertible with an antiaromatic [36]octaphyrin congener (3)b yo xidation with MnO 2 and reduction with NaBH 4 .C uriously,m ild oxidation of 2 with ferrocenium hexafluorophosphate afforded a[ 37]octaphyrin bis(silicon) complex 4 as an stable radical cation that can be stored under ambient conditions in the solid state.O wing to the two NNNCC-five-coordinated Si atoms bearing trigonal bipyramidal geometry,t hese octaphyrin bis(silicon) complexes take on similar and rigid figure-of-eight structures with different consecutive numbers of conjugated p-electrons (38, 37, and 36), and are all stable.

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A Stable Organic π‐Radical of a Zinc(II)–Copper(I)–Zinc(II) Complex of Decaphyrin

Cited by 17 publications

References 43 publications

[30]Hexaphyrin(2.1.2.1.2.1) as Aromatic Planar Ligand and Its Trinuclear Rhodium(I) Complex

[30]Hexaphyrin(2.1.2.1.2.1) as Aromatic Planar Ligand and Its Trinuclear Rhodium(I) Complex

Triggering Redox Activity in a Thiophene Compound: Radical Stabilization and Coordination Chemistry

Synthesis of (bis)Silicon Complexes of [38], [37], and [36]Octaphyrins: Aromaticity Switch and Stable Radical Cation

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