Polycyclic Aromatic Hydrocarbons

Designing a Redox Noninnocent Phenalenyl-Based Copper(II) Complex: An Autotandem Catalyst for the Selective Oxidation of Polycyclic Aromatic Hydrocarbons (PAHs)

“…Oxidation of PAHs is a challenging but very important process related to their derivatization and detoxification. − Moreover, the oxidized products of PAHs such as anthraquinone derivatives are important for the synthesis of industrial-scale hydrogen peroxide, naphthoquinones as dye reagents, and pyrenequinones as photosensitizers in photodynamic therapy. Most of the methods reported in the literature for conversion of PAHs to quinones are achieved through powerful oxidants and harsh reaction conditions. − Therefore, we initiated our study for the catalytic oxidation of PAHs in the presence of a novel [Cu II L] complex 1 derived from nontoxic transition metal and ligand based on an interesting redox-active PLY backbone, which has shown unusual chemistries and a broad spectrum of catalytic properties. We started a typical catalytic process with anthracene 2 in the presence of H 2 O 2 (10 equiv) as a source of oxygen and [Cu II L] complex (10 mol %) at 23 °C in acetonitrile.…”

“…Similarly, extended conjugation present in pyrene shows wide applications pertaining to the photophysical and electronic properties, which makes the pyrene nucleus a valuable component in materials, supramolecular, and biological chemistry . The oxidation of PAHs such as naphthalene, anthracene, and substituted anthracene provides a route for their detoxification, whereas oxidized products such as quinone are commonly used in organic synthesis and medicinal chemistry. − There are a few reports in the literature toward this end, such as oxidation of naphthalene to naphthoquinone by [Ru]/PTC in a H 2 O 2 medium or the Pd­(II)-SP resin using H 2 O 2 and AcOH conditions (see Table ); , oxidation of anthracene to 9,10-anthraquinone using a strong acid like HNO 3 /O 2 or CrO 3 in acetic acid at 90 °C; − metal-catalysis by BW 11 Fe; or, alternatively, oxidation of anthraldehyde to 9,10-anthraquinone using N -bromosuccinimide (NBS) in aqueous N , N -dimethylformamide at 75–80 °C or using gold nanocrystalline diamonds (AuNCD), O 2 , and a 530 nm light-emitting diode (LED) (see Table ). , These conversions suffer from several drawbacks such as hazardous reaction conditions, high temperatures, tedious purification process, and moderate yields.…”

Mutagenic and genotoxic effect of polycyclic aromatic hydrocarbons on health: Mechanisms and Risk assessment

“…Due to BaP's high molecular weight, BaP can mainly absorb and accumulate in surfaces material; however, about 10% of BaP was reported to be in the gas form (K. Liao & Yu, 2020;Masiol et al, 2012). At 25 °C, it is in a solid phase with high lipophilicity that does not solve in water (Ifegwu & Anyakora, 2016). High degradation stability of BaP enables this particle hold to be a hazard agent evaluating total released PAHs (Amadou et al, 2021;Beyea et al, 2006).…”

“…In the liver, an accumulation location of enzymes, the BaP activation, and metabolism initiate and turn the potentially carcinogenic compounds into electrophilic genotoxic forms (Barangi et al, 2020;Delgado-Roche et al, 2019;Ifegwu & Anyakora, 2016).…”

Analytical chemistry, formation, mitigation, and risk assessment of polycyclic aromatic hydrocarbons: From food processing to in vivo metabolic transformation

“…Apart from large interindividual variations in urinary 1‐OHP levels, the PAH profiles vary substantially among sources; hence, urinary 1‐OHP alone does not reflect the overall PAH exposure (Gao et al., 2018; Luch, 2005). Other hydroxylated PAHs, including mono, poly, and multihydroxy PAHs, have been used as biological indicators of PAH exposure, such as 1‐, 2‐hydroxynaphthalene; 2‐, 9‐hydroxyfluorene; 1‐, 2‐, 3‐, 4‐, 9‐hydroxyphenanthrene; 6‐hydroxychrysene and 3‐hydroxybenzo[a]pyrene (Gao et al., 2018; Campo et al., 2010; Martin et al, 1989; Ifegwu & Anyakora, 2016). The urinary concentrations of BaP‐r‐7,t‐8,t‐9,c‐10‐tetrahydrotetrol (BPT I‐1) and BaP‐r‐7,t‐8,c‐9,c‐10‐tetrahydrotetrol were measured in smokers and nonsmokers and results showed that the median concentration of BPT I‐1 in smokers’ urine (0.069 pg/mL) was significantly higher than that in nonsmokers (0.043 pg/mL).…”