Reactions of copper(II) halides with aromatic compounds—IX

Bansal, Sachin; Nonhebel, D. C.; Mancilla, Jerson

doi:10.1016/0040-4020(73)80051-1

Cited by 23 publications

(5 citation statements)

References 16 publications

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“…9,10-Dimethylanthracene was synthesized according to the literature method. 13 1-Hydroxy-2-oxo-3-(3-aminopropyl)-3-methyl-1-triazene (NOC-13, a NO donor with a half-lifetime of 13.7 min) was synthesized using a reported method. 14 Horseradish peroxidase (HRP, RZ = 2.5, >200 U/mg) was purchased from Aladdin.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Mitochondria Targetable Time-Gated Luminescence Probe for Singlet Oxygen Based on a β-Diketonate–Europium Complex

Sun

Song

et al. 2015

Inorg. Chem.

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Singlet oxygen ((1)O2) plays a key role in the photodynamic therapy (PDT) technique of neoplastic diseases. In this work, by using a 9,10-dimethyl-2-anthryl-containing β-diketone, 1,1,1,2,2-pentafluoro-5-(9',10'-dimethyl-2'-anthryl)-3,5-pentanedione (Hpfdap), as a (1)O2-recognition ligand, a novel β-diketonate-europium(III) complex that can act as a luminescence probe for (1)O2, [Eu(pfdap)3(tpy)] (tpy = 2,2',2″-terpyridine), has been designed and synthesized for the time-gated luminescence detection of (1)O2 in living cells. The complex is weakly luminescent due to the quenching effect of 9,10-dimethyl-2-anthryl groups. After reaction with (1)O2, accompanied by the formation of endoperoxides of 9,10-dimethyl-2-anthryl groups, the luminescence quenching disappears, so that the long-lived luminescence of the europium(III) complex is switched on. The complex showed highly selective luminescence response to (1)O2 with a remarkable luminescence enhancement. Combined with the time-gated luminescence imaging technique, the complex was successfully used as a luminescent probe for the monitoring of the time-dependent generation of (1)O2 in 5-aminolevulinic acid (a PDT drug) loaded HepG2 cells during the photodynamic process. In addition, by coloading the complex and a mitochondrial indicator, Mito-Tracker Green, into HepG2 cells, the specific localization of [Eu(pfdap)3(tpy)] molecules in mitochondria of HepG2 cells was demonstrated by confocal fluorescence imaging measurements.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Mitochondria Targetable Time-Gated Luminescence Probe for Singlet Oxygen Based on a β-Diketonate–Europium Complex

Sun

Song

et al. 2015

Inorg. Chem.

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“…(4)] . 34 Another possibility is that chloride is present as a counterion for the radical cation. OMe I OMe I In order to obtain evidence relative to the hypotheses, polymerizations in which' the halide present in the oxidant differed from that in the acid workup were carried out.…”

Section: Scheme I1mentioning

confidence: 99%

Polymerization of aromatic nuclei. XXV. ESR and chemical studies on the radical cation nature of poly(p‐phenylene)

Jones

Kovacic

Howe

1981

J. Polym. Sci. Polym. Chem. Ed.

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SynopsisThe radical cation nature of poly(p-phenylene) (PPP) was examined by electron spin resonance (ESR) and chemical means. ESR studies revealed a radical concentration of 1.0 X 1021 spins/g for the crude polymer. Workup with aqueous acid decreased the value to 1.5 X loL8 spins/g. Reactions of the polymer with certain nucleophiles followed the half-regeneration mechanism, whereas with others, electron transfer mainly occurred. The origin of halogen in the polymer was found to arise from reaction of the radical cation with the oxidant, and not with halide during workup. Oxidation of PPP with various species increased the concentration of radical cations.

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“…1-Bromo-4-methoxynaphthalene 2a: General Procedure for Bromination of 1-Alkoxynaphthalenes.sA mixture of 1a (1.90 g, 12 mmol) and Kieselguhr-supported copper(II) bromide (24 g, 36 mmol) in benzene (150 ml) was stirred at 30 °C for 3 h. The mixture was filtered, and the spent reagent was washed with benzene. The combined filtrates were evaporated, and the residue was distilled under vacuum to give 2.3 g (85%) of 1-bromo-4-methoxynaphthalene 2a bp 155-157 °C at 5 Torr (lit., 6 159-160 °C at 4 Torr).…”

Section: Methodsmentioning

confidence: 99%

“…4,4-Dimethoxy-1,1-binaphthyl 3a.sA mixture of 1a (0.95 g, 6 mmol) and alumina-supported copper(II) chloride (5.56 g, 12 mmol) in benzene was stirred at 30 °C for 1 h. The mixture was filtered and the spent reagent was washed several times with hot benzene. Hexane was added to the combined filtrates, which were concentrated, to precipitate 4,4-dimethoxy-1,1-binaphthyl 3a (0.8 g, 85%) mp 254-255 °C (from hexane-benzene) (lit., 6 252-254 °C). GLC analysis of the filtrate after removal of the material showed the presence of 1-chloro-4-methoxynaphthalene.…”

Section: Methodsmentioning

confidence: 99%

“…The yield of 3 in the reaction using the reagent supported on alumina was slightly higher than that in the reaction using the same reagent supported on Kieselguhr. The reaction of 1a with copper(II) chloride in refluxing benzene gives a mixture of 3a and 4-chloro-and 8-chloro-1-methoxynaphthalene, 6 whereas a similar reaction with alumina-or Kieselguhr-supported copper(II) chloride proceeded smoothly, even at 30 °C, to give selectively 3a in high yield, no 8-chloro-1-methoxynaphthalene being formed. For instance, the reaction fo 1a with alumina-supported copper(II) chloride in benzene at 30 °C for 1 h afforded 3a in 85% yield and 4-chloro-1-methoxynaphthalene in 8% yield.…”

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confidence: 99%

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Regioselective Halogenation and Dimerization of Alkoxynaphthalenes with Alumina- or Kieselguhr-supported Copper(II) Halides†

Suzuki¹,

Takeuchi²,

Kodomari³

1997

J. Chem. Res. (S)

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The reaction of 1-alkoxynaphthalenes 1 with alumina-supported copper(II) bromide or copper(II) chloride gave dimers, 4,4-dialkoxy-1,1-binaphthyls 3, as major products, and with Kieselguhr-supported copper(II) bromide afforded 1-bromo-4-alkoxynaphthalenes 2, while the reaction of 2-alkoxynaphthalenes 4 with alumina-or Kieselguhr-supported copper(II) bromide gave preferentially 1-bromo-2-alkoxynaphthalenes 5.

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Reactions of copper(II) halides with aromatic compounds—IX

Cited by 23 publications

References 16 publications

Mitochondria Targetable Time-Gated Luminescence Probe for Singlet Oxygen Based on a β-Diketonate–Europium Complex

Mitochondria Targetable Time-Gated Luminescence Probe for Singlet Oxygen Based on a β-Diketonate–Europium Complex

Polymerization of aromatic nuclei. XXV. ESR and chemical studies on the radical cation nature of poly(p‐phenylene)

Regioselective Halogenation and Dimerization of Alkoxynaphthalenes with Alumina- or Kieselguhr-supported Copper(II) Halides†

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