Natural Porphyrins Accelerating the Phototransformation of Benzo[a]pyrene in Water

Luo, Lijuan; Xiao, Zidong; Chen, Baowei; Cai, Fengshan; Fang, Ling; Lin, Li; Luan, Tiangang

doi:10.1021/acs.est.7b05854

Cited by 21 publications

(26 citation statements)

References 46 publications

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“…In addition, the major transformation products of BaP via porphyrins were identified as BaP-1,6-dione, BaP-3,6-dione, and BaP-6,12-dione experimentally. 11 , 12 Thus, the Cb1 and Cb2 sites are not considered infra. The subsequent O 2 addition to P0 mainly proceeds in C12, C1, C3, C4, four different pathways, forming the peroxy radicals BaP-6-OH-OO(P1- n ).…”

Section: Resultsmentioning

confidence: 99%

“… 11 , 12 • OH was also detected when BaP was degraded in the natural porphyrin aqueous solution. 11 , 12 Both • OH and 1 O 2 were speculated to play a crucial role in the degradation of PAHs and other organic pollutants. 20 − 25…”

Section: Introductionmentioning

confidence: 94%

“… 12 The major transformation products of BaP via porphyrins were identified as BaP-quinones, including BaP-1,6-dione, BaP-3,6-dione, and BaP-6,12-dione. 11 , 12 Porphyrins have been proven to have excellent photosensitizing properties to generate singlet oxygen, 16 − 19 and the degradation rate of BaP was positively correlated with the 1 O 2 concentrations generated by porphyrin photocatalysis; the higher the singlet oxygen content, the higher the BaP transformation. 11 , 12 • OH was also detected when BaP was degraded in the natural porphyrin aqueous solution.…”

Section: Introductionmentioning

confidence: 99%

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Degradation Mechanism of Benzo[a]pyrene Initiated by the OH Radical and ¹O₂: An Insight from Density Functional Theory Calculations

Chu

Liu

2020

ACS Omega

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The degradation mechanism of benzo[ a ]pyrene (BaP) initiated by • OH and 1 O 2 in aqueous solution is investigated by density functional theory calculations. The main degradation products are BaP-1,6-quinone, BaP-3,6-quinone, BaP-4,6-quinone, and BaP-6,12-quinone. • OH and HO 2 are the main intermediate radical species. At a low initial concentration of • OH, 1 O 2 could be a primary driver for BaP degradation. The degradation mechanism includes six consecutive elementary reactions: (1) 1 O 2 initiation forming BaP-6-OO. (2) 1,3 H-shift (H atom shifts to the OO group) that is promoted by H 2 O, forming BaP-6-OOH. (3) BaP-6-OOH decomposes into the • OH radical and BaP-6-O. (4) • OH addition to BaP-6-O forming BaP-6- O -1(3,4,12)-OH. (5) Extracting the H atom from the carbon with the OH group by 1 O 2 . (6) Extracting the H atom from the OH group by HO 2 . At a high initial concentration of • OH, the • OH-initiated and 1 O 2 -initiated degradation reactions of BaP are both feasible. The degradation mechanism includes six consecutive elementary reactions: (1) • OH initiation forming BaP-6-OH or 1 O 2 initiation forming BaP-6-OO. (2) 1 O 2 addition to BaP-6-OH forming BaP-6-OH-12(1,3,4)-OO or • OH addition to BaP-6-OO forming BaP-6-OO-12(1,3,4)-OH. (3) Extracting the H atom from the carbon with the OH group by 1 O 2 , forming HO 2 . (4) 1,3 H-shift (H-shift from the carbon to the OO group), promoted by H 2 O. (5) The loss of the OH radical. (6) Abstracting the H atom from the OH group by HO 2 . In this paper, the formation of BaP-4,6-quinone via the BaP degradation is first reported. Water participates in the elementary reaction in which the H atom attached on the aromatic ring shifts to the OO group, serving as a bridge that stabilizes the transition state and transports the proton. A comprehensive investigation explains the degradation mechanism of BaP initiated by • OH and 1 O 2 in aqueous solution.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

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Degradation Mechanism of Benzo[a]pyrene Initiated by the OH Radical and ¹O₂: An Insight from Density Functional Theory Calculations

Chu

Liu

2020

ACS Omega

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“…Due to its characteristic tetrapyrrole structure, the photochemical properties of SCC have been well studied by organic photovoltaics and optical spectroscopy [ 21 , 22 , 23 , 24 , 25 ]. However, the effectiveness of SCC as a catalyst in organic reactions has yet to be explored in-depth [ 26 ]. Herein, we describe a highly efficient and practical protocol for the selective catalytic oxidation of benzylic alcohols to aldehydes and carboxylic acids using SCC as a green, safe, and cheap metal-copper catalyst in water.…”

Section: Introductionmentioning

confidence: 99%

Sodium Copper Chlorophyllin Catalyzed Chemoselective Oxidation of Benzylic Alcohols and Diarylmethanes in Water

et al. 2018

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We report the highly efficient and chemoselective oxidation of benzylic alcohols catalyzed by sodium copper chlorophyllin in water, producing corresponding arylcarbonyl compounds. Importantly, the catalytic system exhibits a wide substrate scope and high functional group tolerance. Moreover, secondary alcohols and even diarylmethanes were smoothly oxidized to the desired aryl ketones with excellent yields.

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“…[18][19][20][21][22] Nonetheless, the utilization of SCC as a photosensitizer in organic reactions has yet to be investigated thoroughly. 23,24 A drawback of using chlorophyll as photosensitizer is its instability under thermally or photochemically conditions. There are many reports that show the thermal and photochemical instability of chlorophylls and isolation/characterization of their degradation pathways/products.…”

Section: Introductionmentioning

confidence: 99%

Photosensitizer Using Visible Light

Alzamly

Alawadhi

Ahmed

et al. 2018

Int J Innov Educ Res

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In this experiment, the visible light reactive photosensitizer (PS) derived from chlorophyllin sodium copper salt has been synthesized via a simple synthetic route. The enhanced photocatalytic activity for the decomposition of the pharmaceutical compound Diclofenac Potassium available as Voltfast sachets under visible light irradiation was demonstrated by comparing the photocatalytic decomposition of Diclofenac Potassium in the presence and absence of the new synthesized visible light photosensitizer under the same photocatalytic conditions. Based on the experimental results, higher activity was achieved for the sample composed of the new synthesized visible light photosensitizer. The photosensitized sample using the new derivative of chlorophyllin sodium copper salt exhibited approximately 21 times higher rate when compared with that of Chlorophyllin sodium copper salt sample. This photocatalytic activity can be attributed to the enhanced visible light harvesting of the new derivative of Chlorophyllin sodium copper salt.

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Natural Porphyrins Accelerating the Phototransformation of Benzo[a]pyrene in Water

Cited by 21 publications

References 46 publications

Degradation Mechanism of Benzo[a]pyrene Initiated by the OH Radical and ¹O₂: An Insight from Density Functional Theory Calculations

Degradation Mechanism of Benzo[a]pyrene Initiated by the OH Radical and ¹O₂: An Insight from Density Functional Theory Calculations

Sodium Copper Chlorophyllin Catalyzed Chemoselective Oxidation of Benzylic Alcohols and Diarylmethanes in Water

Photosensitizer Using Visible Light

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Natural Porphyrins Accelerating the Phototransformation of Benzo[a]pyrene in Water

Cited by 21 publications

References 46 publications

Degradation Mechanism of Benzo[a]pyrene Initiated by the OH Radical and 1O2: An Insight from Density Functional Theory Calculations

Degradation Mechanism of Benzo[a]pyrene Initiated by the OH Radical and 1O2: An Insight from Density Functional Theory Calculations

Sodium Copper Chlorophyllin Catalyzed Chemoselective Oxidation of Benzylic Alcohols and Diarylmethanes in Water

Photosensitizer Using Visible Light

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Product

Resources

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Degradation Mechanism of Benzo[a]pyrene Initiated by the OH Radical and ¹O₂: An Insight from Density Functional Theory Calculations

Degradation Mechanism of Benzo[a]pyrene Initiated by the OH Radical and ¹O₂: An Insight from Density Functional Theory Calculations