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WATER RESEARCH · 2024 · IF 11.4

Insight into the photodegradation of methylisothiazolinone and benzoisothiazolinone in aquatic environments

Pengfei Yu,Zhongyu Guo,Jieqiong Wang,Yuchen Guo,Tingting Wang,Lilan Zhang

Methylisothiazolinone (MIT) and Benzisothiazolinone (BIT) are two widely used non-oxidizing biocides of isothiazolinones. Their production and usage volume have sharply increased since the pandemic of COVID-19, inevitably leading to more release into water environment. However, their photochemical behaviors in water environment are still unclear. Therefore, this study investigated photodegradation properties of MIT and BIT in natural water under simulated sunlight. The results demonstrated that direct photolysis was mainly responsible for their photodegradation which occurred through their excited singlet states rather than triplet states. The quantum yields of MIT and BIT photodegradation were 11 - 13.6 × 10 −4 and 2.43 - 5.79 × 10 −4 , respectively. pH had almost no effect on the photodegradation of MIT, while the photodegradation of BIT was significantly promoted under alkaline condition due to abundance of BIT in its deprotonated form (BIT- N − ). Cl − , NO 3 − and dissolved organic matter (DOM) in natural water inhibited the photodegradation of both MIT and BIT, with the light screening effect of DOM being the most significantly inhibitory factor. The addition of other isothiazolinones, which possibly coexisted with MIT and BIT in actual condition, slightly inhibited the photodegradation of MIT and BIT. The estimated half-life under natural sunlight at a 30°N latitude was estimated to be approximately 1.1 days. The photodegradation pathways of MIT and BIT are similar, primarily initiated from the ring-opening at the N-S bond, with Frontier electron densities (FED) calculations suggesting the likelihood of oxidation and ·OH addition reactions at the O, N, and S sites. While the photodegradation products exhibited significantly reduced acute toxicity compared to their parent compounds, they nonetheless posed substantial chronic toxicity. These insights are vital for assessing the ecological impacts of MIT and BIT in aquatic environments.

研究领域: 环境科学 · 生态学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ACS Applied Materials & Interfaces · 2023 · IF 9.5

Boosting Solid-State Luminescence of Thiazolothiazole Viologen by Incorporating Metal Halide Clusters to Hinder π-Stacking

Xuyi Li,Chen Huang,Yu Fan,Zhiang Bai,Bao-Li An,Jiaqiang Xu,Weiwei Zheng,Yue-Ling Bai

A new strategy is developed herein to improve the solid fluorescence of thiazolothiazole viologen by using the ZnCl42– cluster as a scaffold to hinder π-stacking. Importantly, the Cl···H bonds are formed in the solid state to sustain the framework and can be automatically dissociated when dissolved in H2O, thus having no impact on the strong emission in aqueous solution. As such, the first case of organic–inorganic viologen–zinc halide named 4PV·ZnCl4 was designed and synthesized, and a significant increase in photoluminescence quantum yield (ΦF) is realized from 4PV·2Br (ΦF = 0%) to 4PV·ZnCl4 (ΦF = 27.0%) in solid and from 97% to 98% in H2O. 4PV·ZnCl4 also displays pH stimuli-responsive naked-eye chromic behavior and photoluminescence with different coloring states and intensities. The multifunctional performance of 4PV·ZnCl4 provides a prerequisite for carrying different information, expanding their promising application in multilevel information encryption.

研究领域: 化学 · 材料科学 · 光学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF MOLECULAR STRUCTURE · 2021 · IF 3.196

Structures of eleven organic acid-base adducts from 2-aminobenzothiazole/2-aminothiazole and acidic compounds

Xingjun Gao,Yuting Zhang,Qianqian Xie,Weiqiang Xu,Shouwen Jin,Qinqin Ye,Yi Yu,Bin Chen,Hui Liu,Daqi Wang

Cocrystallization of 2-aminobenzothiazole/2-aminothiazole with a set of organic acids got a total of 11 crystalline adducts with the compositions: (2-aminobenzothiazole): (saccharin) [(HL1) + • (sac) − , sac = saccharinate] (1) , (2-aminobenzothiazole): (dichloroacetic acid) [(HL1) + • (dca) − , dca = dichloroacetate] (2) , (2-aminobenzothiazole): (trichloroacetic acid) [(HL1) + • (tca) − , tca = trichloroacetate] (3) , (2-aminothiazole): (glycolic acid) [(HL2) + • (gla) − , gla = glycolate] (4) , (2-aminothiazole): (2-methyl-2-phenoxypropanoic acid) [(HL2) • (mppa), mppa = 2-methyl-2-phenoxypropanoiate] (5) , (2-aminothiazole): ((2,4-dichlorophenoxy)-acetic acid) [(HL2) • (dcpa), dcpa = (2,4-dichlorophenoxy)-acetate] (6) , (2-aminobenzothiazole) 2 : (2,3-dibromo-butanedioic acid) 2 [(HL1) 2 + • (dba) 2- • (H 2 dba), dba = 2,3-dibromo-butanedioate] (7) , (2-aminothiazole): (1,4-cyclohexanedicarboxylic acid) [(L2) 2 • (1,4-H 2 cha), 1,4-H 2 cha = 1,4-cyclohexanedicarboxylic acid] (8) , (2-aminothiazole): (4-nitrophthalic acid) [(HL2 + ) • (4-Hnpa − ), Hnpa −  = 4-nitro hydrogenphthalate] (9) , (2-aminothiazole): (5-hydroxyisophthalic acid) [(HL2 + ) • (5-Hipta − ), 5-Hipta −  = 5-hydroxy hydrogenisophthalate] (10) and (2-aminobenzothiazole): (3-nitrophthalic acid): CH 3 CH 2 OH [(HL1) • (3-Hnpa − ) • CH 3 CH 2 OH, 3-Hnpa −  = hydrogen 3-nitrophthalate] (11) . These adducts have been examined by XRD, IR and elemental analysis and the melting points were also gauged. Their structural and supramolecular aspects are fully analyzed. The result unveils that among the investigated crystalline solids 1 - 7 and 9 - 11 the aryl N in thiazole moieties are protonated when the organic acids are deprotonated, the crystal packing is ruled by the strong charge-assisted N-H⋯O H-bond from the NH + and the deprotonated acids. 8 is a cocrystal sustained by the neutral N-H⋯O/O-H⋯N H-bonds. Except the N-H⋯O H-bonds, the O-H•••O H-bonds were also found at 4, 7 and 9 - 11. 1 has the additional N-H•••S/N-H•••N H-bonds. The N-H•••Cl H-bond was appeared in 3 . Further analysis of the crystal packing told that a different set of additional CH 2 -C, CH-O/CH 2 -O, CH-S, CH-CH, CH-Cl, Cl-Cl, Cl-S, Br-S, Br-π, CH-π/CH 2 -π/CH 3 -π, N-π, C-S, O-C π , O-N, O-O, O-S, π-π and O-π contacts contribute to the stabilization and expansion of the total structures. For the interplay of the various weak nonbonding interactions these structures adopted homo or hetero supramolecular synthons or both. The recognition of the base-acid created the classical R 2 2 (8) synthon in all compounds except 7 . For the cooperation of these weak bonds, 1D-3D structures were made.

研究领域: 化学 · 晶体学 · 超分子化学
✓ 已验证 DOI 高影响因子
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JOURNAL OF MATERIALS SCIENCE · 2022 ·Vol. 57 ·期 44 ·20641-20653 · IF 4.682

Preparation and photocatalytic property of exfoliated poly(phenylenethiazolo[5,4‐d]thiazole) copolymers

Ren Meiqi,Dong Xiaoli,Wang Yu,Zheng Nan,Ma Hongchao,Zhang Xiufang

Conjugated microporous polymers have attracted significant attention in recent years due to their high porosity, broad functionality and excellent chemical stability. In this work, the small-sized layered structure of poly(phenylenethiazolo[5,4-d]thiazole) (p-PhTT) copolymer was achieved by a facile solvothermal-assisted exfoliation process in a polar organic solvent. Owing to the shorter diffusion length, the layered structure could enhance carrier diffusion from the interior to the surface, as well as provide more active sites in photocatalytic reaction. The obtained exfoliated p-PhTT copolymers show good dispersion and stability in aqueous solution and exhibit efficiently photocatalytic activity for degrading rhodamine B dye under visible-light irradiation. This effective method offers a promising strategy for exfoliating other organic porous polymers. Graphical Abstract

CAS / MDL: 623-27-8
研究领域: 材料科学 · 环境科学
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ACS Applied Materials & Interfaces · 2019 · IF 8.456

Layered Thiazolo[5,4-d] Thiazole-Linked Conjugated Microporous Polymers with Heteroatom Adoption for Efficient Photocatalysis Application

Qi Huang,Liping Guo,Ning Wang,Xiang Zhu,Shangbin Jin,Bien Tan

Conjugated microporous polymers (CMPs) with high surface areas, tunable building blocks, and fully conjugated structures have found important applications in optoelectronics. Here, we report a new series of CMPs with tunable band gaps by introducing thiazolo[5,4-d] thiazole as the linkage. Because they are synthetic polymers, the geometries and structures could be rationally designed. Their intrinsic wide visible-light absorption properties and layered architectures endow them with a promising photocatalytic performance. The role of geometries, surface areas, and morphologies of the CMPs in photocatalysis abilities is examined and discussed. The results indicate that geometries have a direct impact on the surface areas and morphologies of the CMPs and thus exert great influence on photocatalysis.

研究领域: 材料化学 · 物理化学 · 高分子科学 · 光催化 · 纳米材料 · 能源化学
✓ 已验证 DOI 高影响因子
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APPLIED CATALYSIS B-ENVIRONMENTAL · 2023 · IF 22.1

Narrowing the bandgaps of thiazolo[5,4-d]thiazole-bridged conjugated microporous polymers to capture green light for selective oxidation of amines

Fengwei Huang,Xiaoyun Dong,Yuexin Wang,Xianjun Lang

Conjugated microporous polymers (CMPs) have evloved into versatile visible light photocatalysts. Narrowing the bandgaps of CMPs could capture more visible light without shifting the suitable position with an established electron acceptor like thiazolo[5,4- d ]thiazole (TzTz). Here, benzene-1,3,5-tricarbaldehyde (Bz-CHO) and benzo[1,2-b:3,4-b':5,6-b'']trithiophene-2,5,8-tricarbaldehyde (BTT-CHO) are adopted to undergo condensation with dithiooxamide, preparing two TzTz-bridged CMPs, namely TzTz-Bz and TzTz-BTT. Thereby, TzTz-BTT could capture visible light more substantially than TzTz-Bz due to narrowing the bandgap. Endowed by TzTz, both TzTz-BTT and TzTz-Bz possess similar positions for the activation of O 2 and can drive the subsequent formation of imines. However, TzTz-BTT, with a narrower bandgap, could capture more green light to drive the electron and proton transfer for the selective formation of imines with higher conversions than TzTz-Bz. This work suggests that CMPs can be equipped with extensive visible light absorption for photocatalytic selective oxidations.

研究领域: 材料科学 · 光催化
✓ 已验证 DOI 高影响因子
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NEW JOURNAL OF CHEMISTRY · 2016 ·Vol. 41 ·期 2 ·747-754 · IF 3.277

Facile synthesis of thiazole-functionalized magnetic microspheres for highly specific separation of heme proteins

Binghai Wang,Juanqiang Wang,Qian Shao,Xingjun Xi,Qiao Chu,Genlai Dong,Yun Wei

A thiazole group containing two kinds of heteroatoms N and S has a large conjugated π bond and strong electronic ability, and it easily binds with metal ions to form metal complexes. In this paper, thiazole as an affinity group was designed to achieve the selective adsorption of heme proteins which have an iron-containing heme group. Thiazole-functionalized magnetic microspheres (Fe3O4@SiO2@AT) were synthesized by immobilizing 2-aminothiazole onto the surface of aminopropyl modified magnetic microspheres through a crosslinking reaction in which glutaraldehyde was a crosslinking agent. The elemental analysis and thermogravimetric data confirmed and quantified the immobilization of the thiazole group. Due to the covalent coordination between the thiazole group (lone pair electrons of the N atom) and the iron ion in the heme group, Fe3O4@SiO2@AT exhibited a high binding capacity for hemoglobin (2.02 g g−1) and a relatively low binding capacity for other proteins (lysozyme as a model protein) without a heme group. Moreover, the whole separation process required only 15 minutes, which was favorable for the separation of unstable proteins. In addition, Fe3O4@SiO2@AT was successfully applied to selectively separate hemoglobin from a binary protein mixture and human blood samples. These results demonstrated that the microspheres had potential use in the separation of heme proteins.

CAS / MDL: 96-50-4
研究领域: 材料科学 · 生物化学 · 分析化学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2019 · IF 2.931

A benzothiazole-rhodol based luminophor: ESIPT-induced AIE and an application for detecting Fe2+ ion

Jianping Guan,Qin Tu,Long Chen,Mao-Sen Yuan,Jinyi Wang

Herein, we designed and synthesized a luminophor, Rh-F , which is an intergrant of rhodol and 2-hydroxy benzothiazole by introducing a benzothiazole unit onto the ortho-position of the phenolic hydroxy of rhodol. Rh-F exhibited excellent fluorescence properties such as a large Stokes shift (>180 nm) and the synergistic effect of aggregation-induced emission (AIE) and an excited state intramolecular proton transfer (ESIPT) feature. The AIE/ESIPT mechanism was thoroughly explored using X-ray single-crystal structures and photophysical determinations. Furthermore, Rh-F showed a sensitive fluorescence response to Fe 2+ with low detection limits of 115.2 nM and high selectivity. Studies of its sensing mechanism indicated that the Fe 2+ -induced blue-green fluorescence-quenched at 525 nm originates from an irreversible Fe 2 + chelate with the oxygen atom of the hydroxyl group and the N atom of the benzothiazole moiety. This blocked the ESIPT process of Rh-F which resulted in the quenching of the fluorescence sensor for Rh-F .

研究领域: 化学 · 材料科学 · 分析化学
✓ 已验证 DOI PubMed 高影响因子
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ChemistrySelect · 2024 ·Vol. 9 ·期 39 ·e202402554 · IF 1.9

The Performance of Amino- and Hydroxy-Substituted Benzothiazoles in Inhibiting the Corrosion of Carbon Steel in HCl and the Molecular-Level Mechanisms

Yu-chen Zhang,Xuan Liang,Rui Ding,An-lan Ji,Yu-han Wang,Ming-di Lei,Jie Fu,Jie Liu

Graphical The corrosion inhibition of NH 2 and OH substituted benzothiazoles on carbon steel in 0.5 mol/L HCl was investigated. 0.0010 mol/L 2-amino-6-hydroxybenzothiazole demonstrated efficient and persistent performance. The adsorption followed Freundlich-Langmuir isotherm. The OH at 6th position extended negative potential region and enhanced coordination activity, resulting in favorable orbital distribution for flat adsorption and feedback bonds. In the pickling process and acidizing program for oil wells, the acidic corrosion of metals is a problem that needs to be addressed. Various acid corrosion inhibitors have been studied and used to mitigate the acidic corrosion of carbon steel. In this paper, the corrosion inhibition of 2-aminobenzothiazole (2 N-BT), 2-amino-4-hydroxybenzothiazole (2 N4O-BT), and 2-amino-6-hydroxybenzothiazole (2 N6O-BT) on carbon steel in 0.5 mol/L HCl was investigated using electrochemical and quantum chemical methods. All three molecules exhibited corrosion inhibition effects. Compared to 2 N-BT, 2 N4O-BT and 2 N6O-BT showed less sensitivity to the environmental conditions and the surface state of the metal. Among them, 0.0010 mol/L 2 N6O-BT demonstrated the highest and most persistent corrosion inhibition, exhibiting a mixed inhibition mechanism with cathodic inhibition dominance. The adsorption of 2 N6O-BT on the carbon steel surface was found to be non-uniform, preferentially adsorbing at certain active sites on the surface, following Freundlich-Langmuir thermodynamic characteristics. It showed initial strongly adsorbed points and weakly adsorbed regions. With continued adsorption of 2 N6O-BT, the differences between strongly adsorbed points and weakly adsorbed regions decreased. The introduction of hydroxyl groups, especially in 2 N6O-BT, extended the negative potential region and enhanced the coordination activity of the molecule, generating the orbital distribution that was advantageous to flat adsorption and the formation of feedback bonds. This provided a molecular structural basis for the excellent corrosion inhibition properties of 2 N6O-BT.

研究领域: 材料科学 · 电化学 · 量子化学
✓ 已验证 产品关联 DOI 高影响因子
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JOURNAL OF MOLECULAR STRUCTURE · 2024 · IF 4

A novel benzothiazole-based fluorescent probe for continuous detection of Cu2+/S2− and its application in cell imaging

Yue Zhao,Mingya Wang,Junli Shi,Mingfeng Han,Yuqi Wu,Shengling Li,Linxiu Zhao,Duanlin Cao

In this paper, a fluorescent probe methyl( E )-2-(3-(benzo[ d ]thiazol-2-yl)-2‑hydroxy -5-methylbenzylidene) hydrazine-1-carboxylate ( DYH ) based on benzothiazole was designed and synthesized. The characterization involved NMR, HRMS, and crystal structure analysis. In case of the existence of other competing cations, the probe DYH showed high-affinity for Cu 2+ , and the resultant DYH Cu 2+ showed exceptional capacity to recognize S 2− in CH 3 CN/HEPES (7/3, v/v, HEPES 0.1 M, pH = 7.3). The detection limits of DYH for Cu 2+ and DYH Cu 2+ for S 2− were 0.56 μM and 0.67 μM, respectively. It was determined that the binding stoichiometry between the DYH and Cu 2+ , as well as DYH Cu 2+ and S 2− , was 1:1 according to the job's curve. The pH of the probe and complex was stable between 4 and 10. Colorimetric experiments of the probe DYH were conducted using test paper as a carrier. Additionally, DYH was used for fluorescence imaging of Cu 2+ and S 2− in Hela cells with poor cellular toxicity and good cell permeability.

研究领域: 分析化学 · 生物医学
✓ 已验证 DOI 高影响因子
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Frontiers of Environmental Science & Engineering · 2020 ·Vol. 15 ·期 5 ·1-12 · IF 4.053

UV-LED/P25-based photocatalysis for effective degradation of isothiazolone biocide

Li Xinzheng,Li Zhiming,Xing Zhihui,Song Zhimin,Ye Bei,Wang Zhengming,Wu Qianyuan

In this work, LED-based photocatalysis using mixed rutile and anatase phase TiO 2 (P25) as the photocatalyst could effectively remove 5-chloro-2-methyl-4-isothiazolin-3-one (CMIT) and methylisothiazolone (MIT) simultaneously, with removal efficiencies above 80% within 20 min. The photocatalytic degradation of both CMIT and MIT could be modeled using a pseudo-first-order rate equation. The photocatalytic degradation rates of CMIT and MIT under LED280 illumination were higher than under LED310 or LED360 illumination. At concentrations below 100 mg/L, the degradation rate of CMIT and MIT under LED illumination significantly increased with increasing catalyst dosage. Additionally, the effects of the chloride ion concentration, alkalinity and dissolved organic matter on the photocatalytic degradation reaction were also investigated. The ·OH free radicals were determined to play the primary role in the photocatalytic degradation reaction, with a degradation contribution of >95%. The photocatalytic degradation of CMIT and MIT mainly occurred via oxidation, hydrolysis, and chain growth reactions. Finally, the possible photocatalytic degradation pathways of CMIT and MIT over LED/P25 are proposed.

研究领域: 环境科学 · 化学工程 · 生物学
✓ 已验证 DOI 高影响因子
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Journal of Water Process Engineering · 2024 · IF 6.3

Synthesis of iodine-povidone-co-thiazole nanoporous membrane with antibacterial activity and application in water treatment

Zhiyan Ma,Xinhua Zhu,Yingru Huang,Yufeng He,Pengfei Song,Rongmin Wang

In order to prevent the spread of the epidemics caused by pathogenic microorganisms, it is very important to explore antimicrobial materials. In this paper, a novel antimicrobial polymer materials with dual active centers, iodine-povidone- co -thiazole nanoporous membrane (IPoTaNm), was successfully synthesized by one-pot emulsion polymerization followed by iodine complexation. The micromorphology and composition were characterized by scanning electron microscope (SEM), Fourier transform infrared spectra (FT-IR), dynamic light scattering (DLS), X-ray photoelectron spectroscopy (XPS), X-ray powder diffraction (XRD) and contact angle test. Then, its antimicrobial performance was measured by using Escherichia coli and Staphylococcus aureus as test strains. It indicated that IPoTaNm exhibits excellent antibacterial activity, which the inhibition rate got to 99.9 % after 48 h. It also presented sustaining bactericidal activity, which the antimicrobial activity maintained 99.9 % even after >7 days. The synergistic antimicrobial mechanism of thiazole units (AcT) and iodine in IPoTaNm was discussed, and some facters for their inhibitory effects in the water column were investigated. In summary, the obtained IPoTaNm with dual active centers was an excellent candidate for minimizing bacteria-infection in different functional materials, which has potential applications in wastewater treatment to reduce bacterial infections.

研究领域: 材料科学 · 生物学 · 环境科学
✓ 已验证 DOI 高影响因子
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