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JOURNAL OF THE CHINESE CHEMICAL SOCIETY · 2022 ·Vol. 70 ·期 1 ·68-75 · IF 1.753

A novel lipid droplets-targeting fluorescent probe based on dicyanisophorone and carbazole for Cu2+ and its application

Yuanyuan Cui,Yaoyang Meng,Yun Hu,Yuqi Chen,Yixian Yang,Min Fang,Cun Li,Weiju Zhu

A novel fluorescent probe, LCH , based on dicyanisophorone and carbazole, was prepared for the visual detection of Cu 2+ . The probe LCH could recognize Cu 2+ by fluorescence quenching in EtOH/H 2 O (1/4, v/v) solution, which could be easily identified under the 365 nm UV lamp, and the detection limit was as low as 0.785 μM. The recognition mechanism of probe LCH with Cu 2+ was determined by combining 1 H NMR titration, MS, and theoretical calculations. Practical application experiments showed that probe LCH could be used to detect Cu 2+ in the test strip experiments. Cell imaging experiments showed that the probe LCH owned good cell permeability and could be applied to the imaging of Cu 2+ in HepG2 cells. In addition, fluorescence colocalization experiments showed that LCH could target lipid droplets. These results indicate that the probe LCH will have a good application prospect in environmental detection and clinical medicine.

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CHINESE JOURNAL OF CHEMICAL ENGINEERING · 2023 · IF 3.8

Insight into the experiment and extraction mechanism for separating carbazole from anthracene oil with quaternary ammonium-based deep eutectic solvents

Xudong Zhang,Yanhua Liu,Jun Shen,Yugao Wang,Gang Liu,Yanxia Niu,Qingtao Sheng

Carbazole is an irreplaceable basic organic chemical raw material and intermediate in industry. The separation of carbazole from anthracene oil by environmental benign solvents is important but still a challenge in chemical engineering. Deep eutectic solvents (DESs) as a sustainable green separation solvent have been proposed for the separation of carbazole from model anthracene oil. In this research, three quaternary ammonium-based DESs were prepared using ethylene glycol (EG) as hydrogen bond donor and tetrabutylammonium chloride (TBAC), tetrabutylammonium bromide or choline chloride as hydrogen bond acceptors. To explore their extraction performance of carbazole, the conductor-like screening   model   for real solvents (COSMO-RS) model was used to predict the activity coefficient at infinite dilution ( γ ∞ ) of carbazole in DESs, and the result indicated TBAC:EG (1:2) had the stronger extraction ability for carbazole due to the higher capacity at infinite dilution ( C ∞ ) value. Then, the separation performance of these three DESs was evaluated by experiments, and the experimental results were in good agreement with the COSMO-RS prediction results. The TBAC:EG (1:2) was determined as the most promising solvent. Additionally, the extraction conditions of TBAC:EG (1:2) were optimized, and the extraction efficiency, distribution coefficient and selectivity of carbazole could reach up to 85.74%, 30.18 and 66.10%, respectively. Moreover, the TBAC:EG (1:2) could be recycled by using environmentally friendly water as antisolvent. In addition, the separation performance of TBAC:EG (1:2) was also evaluated by real crude anthracene, the carbazole was obtained with purity and yield of 85.32%, 60.27%, respectively. Lastly, the extraction mechanism was elucidated by σ -profiles and interaction energy analysis. Theoretical calculation results showed that the main driving force for the extraction process was the hydrogen bonding ((N–H … Cl) and van der Waals interactions (C–H … O and C–H … π), which corresponding to the blue and green isosurfaces in IGMH analysis. This work presented a novel method for separating carbazole from crude anthracene oil, and will provide an important reference for the separation of other high value-added products from coal tar.

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JOURNAL OF MOLECULAR STRUCTURE · 2023 · IF 3.8

Extraction of quinoline from toluene solution of wash oil using 1‑butyl‑3-methylimidazolium hexafluorophosphate ([BMIM] [PF6]): Experimental and molecular dynamics simulations

Yuxiu Fu,Xiaoli Song,Yaming Pang,Yinan Zheng,Liguo Gao

In this paper, a green solvent [BMIM] [PF 6 ] ionic liquid was selected for the extraction and separation of quinoline from simulated wash oil. The effects of extraction temperature, extraction time, and solvent oil ratio on the extraction of quinoline from wash oil were studied. The optimal process parameters were obtained by changing single factor conditions and optimizing the experiment using response surface methodology. When the temperature is 71 ℃, the time is 60 min, and the solvent oil ratio is 3:5, the extraction efficiency can reach 67%. The ionic liquids were recovered and their properties were investigated by infrared spectroscopy. The mechanism of quinoline extraction by ionic liquids was analyzed using infrared spectroscopy and GROMACS kinetic simulation calculations.

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DYES AND PIGMENTS · 2022 · IF 5.122

Ultraviolet activate room temperature ultralong organic phosphorescence from non-crystal benzoylcarbazole-doped polymer system

Jin Wang,Na Li,Xiao-Qin Yang,Li-Li Wang,Rui-Yao Ni

The host-guest doping strategy is widely used in the construction of room temperature phosphorescence (RTP) materials. The current methods for developing carbazole (Cz)-based RTP materials are mainly based on crystallization engineering. Herein, we report a general strategy for carbazole-based RTP materials by doping non-crystal benzoylcarbazole (BzCz) phosphor into polymer matrices . BzCz exhibited fluorescence in solution and RTP in powder state. Notably, the doped BzCz powder@PVA film displays yellow RTP emissions with an afterglow duration of around 7 s. Based on the theoretical calculations, it demonstrated that the co-assembly effect between the BzCz and PVA chains could enhance the long-lived RTP systems. This research provides great convenience for developing carbazole (Cz) molecule-doped polymer RTP materials under ambient conditions.

CAS / MDL: 86-74-8 9003-01-4
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EUROPEAN POLYMER JOURNAL · 2022 · IF 5.546

Porous fluorescent polyaminocarbazole synthesis and their sensing applications

Qingyi Lu,Dongkui Zhang,Feng Xu,Guohang He,Junning Qian,Jiangbin Xia

Porous organic polymers (POPs) have attracted widespread attention in many fields because of their large specific surface area, uniform pore size and high environmental stability. However, the rational synthetic strategy of POPs remains limited and challenging. Herein, the amine group ( NH 2 ) of 9,9′,9″-(benzene-1,3,5-triyl)tris(9H-carbazol-3-amine) (TCBA) and 9-(4-(bis(4-(3-amino-9H-carbazol-9-yl)phenyl)amino)phenyl)-9H-carbazol-3-amine (TCPA) is used as node via chemical oxidation polymerization to fabricate novel star-shaped porous fluorescent polyaminocarbazole (PTCBA and PTCPA). PTCBA and PTCPA not only have large surface area and high environmental stability but also exhibit excellent sensitivity toward Fe 3+ , Cu 2+ and Ru 3+ . Interestingly, Fe 3+ , Cu 2+ and Ru 3+ can be visibly recognized by fluorescent paper strip. We envisage that such porous fluorescent polyaminocarbazole is a promising material in chemsensors.

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ACS Applied Energy Materials · 2022 · IF 6.959

Effect of Hydrophobic Side Chain Length on Poly(carbazolyl terphenyl piperidinium) Anion Exchange Membranes

Zhi Hong Cai,Xue Lang Gao,Wei Ting Gao,Yvonne Shuen Lann Choo,Jia Jun Wang,Qiu Gen Zhang,Ai Mei Zhu,Qing Lin Liu

In recent years, with the continuous application of superacid-catalyzed condensation reaction in the preparation of anion exchange membranes (AEMs), a number of AEMs with excellent performance have been designed. Among them, the method to copolymerize two aromatic compounds with piperidone via a superacid-catalyzed reaction to synthesize anionic conducting copolymers has been widely discussed by researchers. Here, we focus on the introduction of poly(N-alkylcarbazole-co-terphenyl N,N′-dimethylpiperidinium) (PCTP-n), which is formed by copolymerizing different chain lengths of N-alkylcarbazole (AHC, n = 2, 4, and 6) and p-terphenyl with 1-methyl-4-piperidone (1M4P). As a result of the high-curvature backbone and hydrophobic flexible side chains, the PCTP-n AEMs show comprehensive performance advantage. Among them, the PCTP-6 membrane, with an ultralow swelling (7.9%) and an excellent OH– conductivity retention (91.9% in 2 M NaOH at 80 °C after 1080 h), highlights high dimensional stability and alkaline resistance. Then, the PCTP-2 membrane displays excellent mechanical robustness (EB: 40%, TS: 20 MPa) and a decent OH– conductivity (134 mS cm–1 at 80 °C). Furthermore, the PCTP-2-based single cell exhibits a decent power density of 542 mW cm–2 under H2–O2 condition.

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JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY · 2022 · IF 5.141

Carbazole-siloxane based polymers for the selective detection of 4-nitrophenol and Fe3+

Aijing Wang,Minggang Tian,Yujing Zuo,Zhiming Gou

Silicone-containing polymers have broad application prospects in the detection of many analytes due to their unique fluorescence properties. Environmental pollutants are very complex, which have prompted researchers to explore different detection methods. In this report, two kinds of polymers were synthesized via Heck-reaction between tetramethyltetravinylcyclotetrasiloxane (D 4 vi ) and carbazole derivatives. The polymers showed excellent fluorescent properties and exhibited high sensitivity to 4-nitrophenol (4-NP) and Fe 3+ in solution. Furthermore, the polymers still showed high sensitivity for Fe 3+ in living cells. We estimate that the cyclic structure of D 4 vi and carbazole structure will serve as responsive sites for Fe 3+ and 4-NP, respectively. The frontier molecular orbitals of polymers were calculated by Materials Studio and the effect of the cyclic structure of D 4 vi on their responsiveness had been discussed. The design idea of the polymer sensors can provide a new direction for the synthesis of multi-response polymer fluorescent probes.

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Micro & Nano Letters · 2022 ·Vol. 17 ·期 6 ·125-133 · IF 0.98

A photoelectrochemical sensor based on β-cyclodextrin-modified MoS2 quantum dots-WS2 nanosheet composites for the detection of benzo [a]pyrene

Jian-Jun Shi,Zhe Wang,Yan Wang,Rui-Wen Shu,Ping Yang

A photoelectrochemical sensor has been developed for the detection of the polycyclic aromatic hydrocarbon pollutant benzo [a]pyrene (BaP). An n -butyl lithium intercalation stripping method is applied to prepare tungsten disulphide nanosheets (WS 2 NSs). WS 2 NSs and β-cyclodextrin (β-CD)-modified MoS 2 quantum dots (QDs) are then compounded by hydrogen bonding between the amino and hydroxyl groups. After assembly on an indium tin oxide electrode, the energy level matching and synergistic photoelectric effect between β-CD-MoS 2 QDs and WS 2 NSs reduced the combination of photogenerated electrons and holes and an enhanced photocurrent signal is observed. As a result of the host–guest interaction between β-CD and BaP, BaP could bind to the β-CD-MoS 2 QDs in the nanocomposites, which hinders the electron migration to the electrode and weakened the photocurrent signal. Thus, the trace detection of BaP is realized. The rate of photocurrent change is also related to the BaP concentration from 1 to 20 nmol/L with a detection limit of 0.33 nmol/L. In summary, a highly sensitive and selective photoelectrochemical sensor for the detection of BaP is successfully constructed.

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ACS Applied Materials & Interfaces · 2022 · IF 10.383

Micro-/Mesoporous Fluorescent Polymers and Devices for Visual Pesticide Detection with Portability, High Sensitivity, and Ultrafast Response

Weizhong Li,Jinyu Tang,Zhonggang Wang

The residue of pesticides in crops, soil, and water continues to be a widespread concern due to the threat to human health and food safety. With the aim to develop highly sensitive sensing materials and portable detection devices, two dicarbazole-based fluorescent micro-/mesoporous polymers (JYs) with a larger specific surface area and pore sizes ranging from 1.1 to 34.2 nm are synthesized. The Stern–Volmer constants of JY fluorescence quenching for imidacloprid (50,063 M–1) exceed 23–51 times those of the reported porous organic polymers (980–2173 M–1). Of particular interest is the observation that JYs show rapid fluorescence response (2 s) and ultralow detection limit (30 ppb) for imidacloprid in water medium. The pronounced chemsensing property is attributed to the synergistic role of the hierarchical pore structure, large π-conjugation of chromophore groups, and strong inner filter effect between the polymer and imidacloprid molecule. Moreover, the pesticide detection of JYs exhibits good interference resistance in complicated service environments such as the extract liquids of the apple peel and field soil as well as aqueous solutions of various cations and anions. Because of the portability, excellent reusability, and sensitive fluorescence response, the prepared JYs and detection devices have promising applications in the on-site monitoring and early warning of the pesticide residues.

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JOURNAL OF POLYMER SCIENCE · 2021 ·Vol. 59 ·期 23 ·3020-3028 · IF 0

A class of azocarbazole-based carboxylates: High-efficiency ionic unimolecular photobase generators for thiol-epoxy click polymerization under blue light

Can Xu,Xiang Wu,Ying Xiong,Zhen Li,Hongding Tang

Two new unimolecular azocarbazole-based visible photobase generators (Ac-C-Base) with different strong bases such as 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) and 1,1,3,3-tetramethylguanidine (TMG) as the potential active species were prepared. Their structures were confirmed by 1 H NMR, 13 C NMR, and HR-MS. According to the photolysis and EPR results, Ac-C-Base could generate free radicals and strong bases simultaneously through the photodecarboxylation mechanism under 455 nm LED irradiation. Thus they can effectively catalyze the thiol-epoxy polymerization without post exposure baking under light exposure. In addition, the Ac-C-TBD containing a stronger base shows a faster polymerization rate and higher epoxy conversion. Graphical

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BRAZILIAN JOURNAL OF CHEMICAL ENGINEERING · 2021 ·Vol. 38 ·期 2 ·265-272 · IF 1.232

Covalent immobilization of glucose dehydrogenase onto graphene oxide magnetic nanoparticles to improve the stability

Wang Jianfeng,Zhao Make,Lu Xiaoli,Gu Hongbing,Liu Baoquan

Glucose dehydrogenase, as an important biocatalyst, has been widely used in biosensors, especially in measuring blood glucose levels. The low stability of the enzyme limits its applications in clinics and industry. To improve the stability, graphene oxide nanoparticles were fabricated, characterized, and used to immobilize of glucose dehydrogenase. The nanoparticles were characterized by FTIR. The enzyme was covalently immobilized on the nanoparticles with the activation of glutaraldehyde. After optimizing the immobilization conditions, an immobilization yield of 92% and the activity recovery of 91% were achieved. The immobilized GDH was characterized and compared with the free enzyme. It showed 6.9-fold higher stability than that of the free enzyme after the immobilization. And after 25 cycles, the immobilized GDH remained 50% of the initial activity. These results indicated that the immobilization could broaden the applications of the GDH in the industry and clinic.

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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2021 · IF 8.128

Fabricating intramolecular donor-acceptor system via covalent bonding of carbazole to carbon nitride for excellent photocatalytic performance towards CO2 conversion

Xianghai Song,Xinyu Zhang,Mei Wang,Xin Li,Zhi Zhu,Pengwei Huo,Yongsheng Yan

Photocatalytic conversion of CO 2 into hydrocarbon fuels is an ideal technology of mitigating greenhouse effect caused by excessive emission of CO 2 . However, the high recombination rate of electron-hole pairs and limited charge carriers transport speed constrained the catalytic performance of many semiconductor catalysts. In this contribution, a series of carbon nitride (g-CN) samples with intramolecular donor-acceptor (D-A) system were successfully prepared by introducing organic donor into their structures. Characterization results confirmed that carbazole was successful connected to the structure of g-CN via chemical bond. The formation of intramolecular D-A system greatly enlarged the light response region of g-CN-xDbc. In addition, a new charge transfer transition mode was formed in g-CN-0.01Dbc due to the incorporation carbazole, which enable it to use light with energy lower than the intrinsic absorption of g-CN. Meanwhile, the D-A structure led to the spatial separation of electrons and holes in g-CN-xDbc and significantly decreased the recombination rate of electron-hole pairs. The g-CN-0.01Dbc presented the best catalytic performance and the CO evolution rate was 9.6 times higher than that of g-CN. Moreover, the reaction was performed in water without any additive, which made it green and sustainable. DFT simulation confirmed the D-A structure and charge carrier migration direction in the prepared samples.

CAS / MDL: 86-74-8 6825-20-3
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