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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2022 · IF 4.831

A naphthol hydrazone Schiff base bearing benzothiadiazole unit for fluorescent detection of Fe3+ in PC3 cells

Brian Musikavanhu,Dongwei Zhu,Mengran Tang,Zhaoli Xue,Shengjun Wang,Long Zhao

Naphthol hydrazone derivatives are recognized as efficient chelating agents for both qualitative and quantitative detection of metal ions. Here we design a naphthol hydrazine-based chemosensor with covalently linking a strong electron-withdrawing benzothiadiazole group to modulate the molecular electronic structure, nominated as NtHzBtd . The fluorescent probe performs excellent selectivity and sensitivity towards Fe 3+ with 1:1 binding stoichiometry, while exhibiting a quick response at 55 s with a relatively low limit of detection of 0.036 µM. A series of spectroscopic measurements in tandem with theoretical calculations suggest that the probe undergoes both intramolecular charge transfer (ICT) and chelation enhanced quenching (CHEQ) processes. Successful color rendering of paper strips and bioimaging in PC3 cells demonstrate the promising applicability of NtHzBtd for portable Fe 3+ detection in real samples and biosystems.

研究领域: 分析化学 · 生物医学
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JOURNAL OF FLUORESCENCE · 2022 ·Vol. 32 ·期 6 ·2077-2086 · IF 2.525

A Benzothidiazole-Based Reversible Fluorescent Probe with Excellent Performances in Selectively and Sensitively Sensing of Hg2+ in Water

Yu Bo,Yuan Ruimin,He Tianzhi,Liang Lijuan,Huang Kun

The development of mercury ion selective fluorescent probe is significant because it is one of toxic heavy metals and poses great risks and hazards to human health. Herein, we develop a mercury ion-selective fluorescent probe, namely IB , based on imidazole decorated benzothiadiazole that obtained by a facile palladium catalytic C-N coupling reaction. IB exhibits high selectivity and sensitivity towards mercury ion in water with nearly 32-fold fluorescent enhancement. The detection limit is calculated to be 0.93 nmol/L. In addition, the sensing of mercury ion can be conducted in a wide pH scope ranging from 4.0 to 10.0. Subsequently, the mercury ion elicits fluorescence of IB solution can be quenched by the addition of cyanide anions, showing “off-on-off” fluorescence transformation with at least 5 cycles, demonstrating the reversible sensing ability of IB . Furthermore, an INHIBIT logical detector has been developed using mercury ion and cyanide anions as inputs and fluorescence of IB as output. Significantly, IB can be utilized for mercury ion detection in real water sample.

研究领域: 化学 · 环境科学 · 分析化学
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TALANTA · 2020 · IF 5.339

Imidazole-fused benzothiadiazole-based red-emissive fluorescence probe for lysosomal pH imaging in living cells

Lingling Li,Yang Li,Yijing Dang,Tingting Chen,Ao Zhang,Chunyong Ding,Zhiai Xu

Intracellular pH is a key physiological factor for controlling the activities and functions of cells and lysosome is a vital subcellular organelle. Thus, developing a novel lysosome-targeting fluorescence probe for selective and sensitive detection of lysosomal pH in living cells is very important. In this work, we synthesized a series of fluorescence probes based on imidazole-fused benzothiadiazole . The optical properties of these probes were easily adjusted by modifying the substituents with different electron-withdrawing/donating ability in imidazole moiety. All of them showed acid-response and decreased fluorescence intensity during pH values changing from 4.0 to 8.5. The introduction of morpholine group allowed them to specifically respond to the changes of lysosomal pH. Among them, probe MIBTAA possessed a suitable p K a value (5.3) and showed good linear response to pH (R 2  = 0.9918) with red emission when pH changed from 4.4 to 5.6. The probe was successfully applied for monitoring pH variation in living cells induced by proton-pump inhibitor Baf-A1 and chloroquine , indicating its great potential for pH imaging in biological applications.

CAS / MDL: 88899-55-2
研究领域: 生物化学 · 细胞生物学 · 医学影像学
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Polymer Chemistry · 2018 ·Vol. 9 ·期 35 ·4468-4475 · IF 4.927

The effect of molecular structure and fluorination on the properties of pyrene-benzothiadiazole-based conjugated polymers for visible-light-driven hydrogen evolution

Chang Cheng,Xunchang Wang,Yaoyao Lin,Luying He,Jia-Xing Jiang,Yunfeng Xu,Feng Wang

The development of highly efficient organic photocatalysts for water splitting into hydrogen is one of the key challenges in materials chemistry. Herein, we have designed and synthesized a series of conjugated polymers with either a one- or three-dimensional framework consisting of pyrene and benzothiadiazole with different numbers of fluorine substitutions (0 or 2). The effect of molecular structure and fluorine substitution on their catalytic activity was investigated. It was found that the linear non-fluorinated polymer L-PyBT exhibited the highest hydrogen evolution rate up to 83.7 μmol h−1 under visible light irradiation among the prepared polymers because of its broad light absorption, suitable energy bandgap, and enhanced charge generation and separation process.

研究领域: 材料化学 · 光催化 · 能源材料 · 高分子化学 · 光功能材料
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ECS Journal of Solid State Science and Technology · 2021 ·Vol. 10 ·期 7 ·076003 · IF 2.07

Neutral Black Color Showing Electrochromic Copolymer based on Dithienopyrroles and Benzothiadiazole Derivatives

Bin Hu

A novel monomer of 4-(4H-dithieno[3,2-b:2',3'-d]pyrrol-4-yl)-N,N-dimethylaniline (TPDA) based on pyrrole and thiophene units was designed and synthesized, with the homopolymer and copolymer with 4,7-di(2,3-dihydro-thieno[3,4-b][1,4]dioxin-5-yl)benzo[1,2,5]thiadiazole (BDT) prepared by an electrochemical method. Both polymers exhibited good electrochemical properties. Spectroelectrochemical features were investigated using an electrochemical station and UV–vis spectrophotometer. PTPDA film showed orange color in the neutral state and blue color for the oxidation state while PBDT film exhibits a neutral green color and light blue for the oxidation state. The copolymer film can cover the entire visible region due to its possessing the absorption features of both PTPDA and PBDT films, which exhibits black color in the neutral state (0 V) and blue color in the oxidation state (1.0 V). In addition, both the homopolymer and copolymer exhibit good electrochemical stability and coloration efficiency. These electrochromic properties make them as potential candidates for applications.

CAS / MDL: 75-09-2
研究领域: 材料科学 · 化学
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JOURNAL OF HAZARDOUS MATERIALS · 2016 · IF 4.836

Abiotic reduction of trifluralin and pendimethalin by sulfides in black-carbon-amended coastal sediments

Wenwen Gong,Xinhui Liu,Shuhua Xia,Baocui Liang,Wei Zhang

Dinitroaniline herbicides such as trifluralin and pendimethalin are persistent bioaccumulative toxins to aquatic organisms. Thus, in-situ remediation of contaminated sediments is desired. This study investigated whether black carbons (BCs), including apple wood charcoal (BC1), rice straw biochar (BC2), and activated carbon (BC3), could facilitate abiotic reduction of trifluralin and pendimethalin by sulfides of environmentally-relevant concentrations in anoxic coastal sediments. The reduction rates of trifluralin and pendimethalin increased substantially with increasing BC dosages in the sediments. This enhancing effect was dependent on BC type with the greatest for BC3 followed by BC1 and BC2, which well correlated with their specific surface area. The pseudo-first order reduction rate constants ( k obs ) for BC3-amended sediment (2%) were 13- and 14 times the rate constants in the BC-free sediment. The reduction rates increased with increasing temperature from 8 to 25   °C in the BC-amended sediment, following the Arrhenius relationship. Finally, through molecular modeling by density functional theory and reaction species identification from mass spectra, molecular pathways of trifluralin and pendimethalin reduction were elucidated. In contrary to the separate sequential reduction of each nitro group to amine group, both nitro groups, first reduced to nitroso, then eventually to amine groups.

研究领域: 环境科学 · 化学
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ORGANIC ELECTRONICS · 2018 · IF 3.68

Benzothiadiazole, hexylthiophen and alkoxy benzene based solution processable copolymer: Effect of the electron withdrawing substituents (fluorine atoms) on electrochemical, optical and electrochromic properties

Zhen Xu,Hongmei Du,Mengjie Yin,Bozhen Wang,Jinsheng Zhao,Yu Xie

4,7-Bis(4-hexyl-5-(trimethylstannane) -2-thienyl) −2,1,3-benzothiadiazole (HTBT) coupled with 2,5-bis (decyloxy)-1,4-dibromobenzene to afford the donor-π-bridge-donor-acceptor conjugated poly (4,7-bis (4-hexyl-2-thienyl) −2,1,3-benzothiadiazole-co-p-didecyloxybenzene) (PTBTB). Further, copolymerization of fluorine-functionalized HTBT moiety with alkoxyl benzene π-bridge using Stille crossing-coupling reaction yield PTBTB-F. The optical, electrochemical, fluorescent, spectroelectrochemical and electrochromic switching properties of two polymers with different acceptors are studied in detail. Both polymers exhibit excellent solubility in conventional organic solvents , high thermal stability and favorable fluorescence properties. The combination of a strong electron withdrawing pendant group (fluorine atoms) with benzothiadiazole (BT) backbone significantly influences the electrochemical redox, optical and electrochromic behaviors of conducting polymers . The introduction of fluorine atoms to BT lead to a higher oxidation onset potential, but an improved electrochemical n-doping process. The optical band gaps (E g ) of PTBTB and PTBTB-F films are calculated to be 2.02 eV and 1.91 eV, respectively. PTBTB and PTBTB-F films exhibited obvious and reversible color switching between their neutral and oxidized states with high optical contrasts as well as favorable response times, making the polymers unique candidates for flexible organic electrochromic device applications.

研究领域: 材料科学 · 有机化学
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Analytical Methods · 2015 ·Vol. 7 ·期 22 ·9604-9608 · IF 1.821

An efficient colorimetric and fluorescent probe for the detection of fluoride ions based on a benzothiadiazole derivative

Yanhua Yu,Changzhi Dong

In this paper, an efficient colorimetric and fluorescent probe based on a benzothiadiazole derivative was developed for the detection of fluoride ions (F−). The selectivity of this approach capitalized on the highly selective and straightforward chemical reaction between F− and the Si–O bond. The sensing behavior of this probe towards anions was monitored by UV-visible and fluorescence spectroscopies in acetonitrile–aqueous buffer mixtures. Among the tested anions: F−, Cl−, Br−, I−, ClO4−, NO3−, CN−, HSO4−, AcO− and H2PO4− only F− induced a remarkable red-shift (149 nm) in the absorption spectrum which is concomitant with a color change from colorless to pink. This probe provides a new approach for naked-eyed detection of F− and the detection limit was calculated to be 1.7 μM. Besides, a concomitant fluorescence decrease was also observed. These results demonstrated that the probe could detect F− with excellent sensitivity and selectivity in complicated samples.

CAS / MDL: 67-64-1
研究领域: 分析化学 · 环境科学
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Journal of Materials Chemistry C · 2016 ·Vol. 4 ·期 38 ·9094-9102 · IF 5.066

Facile synthesis of benzothiadiazole-based chromophores for enhanced performance of second-order nonlinear optical materials

Ming Li,Hui Zhang,Yan Zhang,Baoshan Hou,Chuangyang Li,Xibin Wang,Ji Zhang,LingHan Xiao,Zhanchen Cui,Yuhui Ao

Novel benzothiadiazole-based second-order nonlinear optical (NLO) chromophores with different push–pull structures were developed. Incorporation of benzothiadiazole (BTD) as a bridge for improving the electro-optic (EO) coefficient (r33) of bulky materials has not been well investigated, despite its extensive application in other photonic materials as electron acceptor. NMR and MS have been used to characterize the structure of synthesized chromophores 5–7. Optical properties have been investigated by UV-vis spectra. Density functional theory calculations have been used to calculate the first-order hyperpolarizability (β) of chromophores r1, 5a, 7a and 5b. Moreover, the poling results of guest–host EO polymers, 5a/PC and 5b/PC, afforded good r33 values of 67 pm V−1 and 45 pm V−1, respectively. All the results demonstrated an improvement in both micro- and macroscopic nonlinearity after incorporation of BTD into chromophores.

研究领域: 材料科学 · 光学
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Polymers · 2017 ·Vol. 10 ·期 1 ·23 · IF 3.364

Effects of Fluoro Substitution on the Electrochromic Performance of Alternating Benzotriazole and Benzothiadiazole-Based Donor–Acceptor Type Copolymers

Yan Zhang,Lingqian Kong,Xiuping Ju,Jinsheng Zhao

Two new donor–acceptor type electrochromic copolymers containing non-fluorinated and di-fluorinated benzothiadiazole analogues, namely P(TBT-TBTh) and P(TBT-F-TBTh), were synthesized successfully through chemical polymerization. Both polymers were measured by cyclic voltammetry, UV-vis spectroscopy, colorimetry and thermogravimetric analysis to study the influence of fluoro substitution on the electrochromic performance. The results demonstrated that the two polymer films displayed well-defined redox peaks in pairs during the p-type doping, and showed distinct color change from dark gray blue to light green for P(TBT-TBTh) with the band gap of 1.51 eV, and from gray blue to celandine green for P(TBT-F-TBTh) with the band gap of 1.58 eV. P(TBT-F-TBTh) presented lower highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels, and better stability than P(TBT-TBTh). It was found that the two fluorine atoms participated in not only inductive effects but also mesomeric effects in the P(TBT-F-TBTh) backbone. In addition, the polymers exhibited high optical contrasts, short response time, and favorable coloration efficiency, especially in the near infrared region. The characterization results indicated that the two reported polymers can be the potential choice as electrochromic materials.Keywords:electrochromism;donor–acceptor type polymers;benzotriazole;benzothiadiazole;fluorination

研究领域: 材料科学 · 化学
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International Journal of Electrochemical Science · 2023 · IF 1.5

Synthesis and Electrochromic Properties of Two Random Copolymers Containing Benzotriazole, Benzothiadiazole as Electron Acceptors and Benzodithiophene or Indacenodithiophene as Electron Donors

Shaowen Pei,Xiuping Ju,Jinsheng Zhao,Hongmei Du

Two random copolymers, poly (benzotriazole-indacenodithiophene-benzothiadiazole) (PBTIDBD) and poly (benzotriazole-benzodithiophene-benzothiadiazole) (PBTBDBD) were synthesized and characterized by electrochemistry, spectroelectrochemistry, electrochromic switching, colorimetry and thermal gravimetric analysis. For PBTIDBD, the color of film changed from rosybrown in neutral state to transparent lightgrey in oxidized state. The band gap calculated according to the spectroelectrochemistry data is 1.86 eV, and the response time, optical contrast, coloration efficiency at 1560 nm are 1.04 s, 62.1%, 276.29 cm 2 ∙C -1 , respectively. And, for PBTBDBD, its color changes from rosybrown to transparent grey as it was fully oxidized. The band gap is 1.68 eV, and the response time, optical contrast, coloration efficiency at 1560 nm are 2.68 s, 62.4%, 193.31 cm 2 ∙C -1 , respectively. Both copolymers are stable at a high temperature, and the decomposition temperature of PBTIDBD and PBTBDBD are 463 °C and 326 °C. Both copolymers can be good candidates for electrochromic application.

研究领域: 材料科学 · 电化学
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TALANTA · 2023 · IF 6.1

Liquid core fluorescent organic nanoprobes: Long-term stability and highly selective lipid droplets bio-imaging

Lihua Tang,Didi Hu,Jingyu Feng,Longchun Li,Yingcui Bu,Hongping Zhou,Xiaoping Gan

Lipid droplets (LDs) are important subcellular organelles that play a huge role in cell metabolism and growth. In this study, we synthesized two LDs fluorescent probes with benzothiadiazole (BTH) as electron acceptor and triphenylamine (TPA) as electron donor , which named as TPA-BTH1 and TPA-BTH2 , respectively. Meanwhile, we introduced long alkyl chain to the probe as a shielding group and LDs targeting enhancement group. The results showed that the two probes were too sensitive to solvents’ polarity because of the D-A structures possessed twisted intramolecular charge-transfer (TICT) effect. Furthermore, we prepared the two probes into nanoprobes by nanoprecipitation, which named as TPA-BTH1-20 and TPA-BTH2-20 , respectively. The nanoprobes also had excellent fluorescence emission abilities and biocompatibility, as well as high photostability and accurately target LDs ability, which could be successfully applied in cell fluorescence imaging experiments.

研究领域: 细胞生物学 · 生物医学工程
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