Synthesis and behavior of novel phthalocyanines possessing intramolecular crown ether bridges between their different aromatic rings for effective extraction multi metal inclusion

Matsunami, Masato; Takaki, Akinobu; Maekawa, Hirofumi; Nishiguchi, Ikuzo

doi:10.1016/j.stam.2004.11.012

Cited by 9 publications

(1 citation statement)

References 12 publications

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“…Apart from measurement using specially calibrated radiation meters, there are no materials that can be applied to the rapid detection of microscopically distributed caesium cations using a simple procedure. Host–guest supramolecular materials promise simple detection of a variety of chemical species, especially specific ions [15–18]. Host–guest interactions may be converted into detectable signals such as electrical and optical outputs while, for instance, fluorescent molecular sensing materials provide greater spatial resolution [19–21].…”

Section: Introductionmentioning

confidence: 99%

Micrometer-level naked-eye detection of caesium particulates in the solid state

Mori

Akamatsu

Sumita

et al. 2013

Science and Technology of Advanced Materials

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Large amounts of radioactive material were released from the Fukushima Daiichi nuclear plant in Japan, contaminating the local environment. During the early stages of such nuclear accidents, iodine I-131 (half-life 8.02 d) is usually detectable in the surrounding atmosphere and bodies of water. On the other hand, in the long-term, soil and water contamination by Cs-137, which has a half-life of 30.17 years, is a serious problem. In Japan, the government is planning and carrying out radioactive decontamination operations not only with public agencies but also non-governmental organizations, making radiation measurements within Japan. If caesium (also radiocaesium) could be detected by the naked eye then its environmental remediation would be facilitated. Supramolecular material approaches, such as host–guest chemistry, are useful in the design of high-resolution molecular sensors and can be used to convert molecular-recognition processes into optical signals. In this work, we have developed molecular materials (here, phenols) as an optical probe for caesium cation-containing particles with implementation based on simple spray-on reagents and a commonly available fluorescent lamp for naked-eye detection in the solid state. This chemical optical probe provides a higher spatial resolution than existing radioscopes and gamma-ray cameras.

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Section: Introductionmentioning

confidence: 99%

Micrometer-level naked-eye detection of caesium particulates in the solid state

Mori

Akamatsu

Sumita

et al. 2013

Science and Technology of Advanced Materials

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Synthesis and characterization of new monomeric and polymeric phthalocyanines

Bílgín

Yağcı

Mendi

et al. 2008

J of Applied Polymer Sci

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Synthesis, Supramolecular Behavior, and In Vitro Photodynamic Activities of Novel Zinc(II) Phthalocyanines “Side‐strapped” with Crown Ether Bridges

Chen¹,

Ke²,

Li³

et al. 2013

Chemistry An Asian Journal

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Two new tetra- or di-α-substituted zinc(II) phthalocyanines 5 and 6 have been prepared through a "side-strapped" method. In the molecules, the adjacent benzene rings of the phthalocyanine core are linked at α-position through a triethylene glycol bridge to form a hybrid aza-/oxa-crown ether. The tetra-α-substituted phthalocyanine 5 shows an eclipsed self-assembly property in CH2Cl2 and the effect on the di-α-substituted analogue 6 is significantly weakened. Furthermore, the crown ethers of these compounds can selectively complex with Fe(3+) or Cu(2+) ion in DMF, leading to formation of J-aggregated nano-assemblies, which can be disaggregated in the presence of some organic or inorganic ligands, such as triethylamine, tetramethylethylenediamine, CH3COO(-), or OH(-). In addition, both compounds are efficient singlet oxygen generators with the singlet oxygen quantum yields (Φ(Δ)) of 0.54-0.74 in DMF relative to unsubstituted zinc(II) phthalocyanine (Φ(Δ)=0.56). They exhibit photodynamic activities toward HepG2 human hepatocarcinoma cells, but the compound 6, which has more than 40-fold lower IC50 value (0.08 μM) compared to the analogue 5 (IC50=3.31 μM), shows remarkablely higher in vitro photocytotoxicity due to its significantly higher cellular uptake and singlet oxygen generation efficiency. The results suggest that these compounds can serve as promising multifunctional materials both in (opto)electronic field and photodynamic therapy.

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Synthesis and behavior of novel phthalocyanines possessing intramolecular crown ether bridges between their different aromatic rings for effective extraction multi metal inclusion

Cited by 9 publications

References 12 publications

Micrometer-level naked-eye detection of caesium particulates in the solid state

Micrometer-level naked-eye detection of caesium particulates in the solid state

Synthesis and characterization of new monomeric and polymeric phthalocyanines

Synthesis, Supramolecular Behavior, and In Vitro Photodynamic Activities of Novel Zinc(II) Phthalocyanines “Side‐strapped” with Crown Ether Bridges

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