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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2025 · IF 4.6

Effects of mono-substituents on the polarity-sensitive fluorescent probe properties of pyrene

Haiyan Wang,Jing Zhang,Yong Zhang

This study investigates the effects of mono-substituents (i.e., hydroxyl, methyl, amino and nitro groups) on the polarity-sensitive fluorescent probe properties of pyrene (Pyr) using fluorescence, UV–vis, and circular dichroism absorption spectroscopy. The results indicate that the four mono-substituents altered the fluorescence spectral characteristics of Pyr to varying degrees, with the most to least influential order being: nitro, amino, hydroxyl, and methyl. 1-Aminopyrene (1-APyr) and 1-nitropyrene (1-NPyr) are deemed unsuitable for use as polarity-sensitive fluorescent probes due to their limited or absent spectral characteristics. The I 386 /I 406 and I 376 /I 396 ratios of 1-HPyr and 1-MPyr decrease as solvents polarity increases, contrasting with the I 372 /I 384 ratio of Pyr. Thus, 1-hydroxypyrene (1-HPyr) and 1-methylpyrene (1-MPyr) also exhibit polarity-sensitive characteristics similar to Pyr, and their solubility in PBS buffer surpasses that of Pyr at 298 K. Moreover, 1-HPyr and 1-MPyr are practicable for detecting the polarity of human serum albumin (HSA) under simulated physiological conditions. The results underscore the potential of the polarity-sensitive mono-substituents of Pyr in biological applications, particularly in probing protein polarity and conformational changes, and further providing a potential tool for the related research in biochemistry and pathology.

CAS / MDL: 930-55-2
研究领域: 生物化学 · 病理学 · 分子生物学
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JOURNAL OF APPLIED ELECTROCHEMISTRY · 2018 ·Vol. 48 ·期 10 ·1121-1129 · IF 2.262

Multi-colored electrochromic devices based on mixed mono- and bi-substituted 4,4′-bipyridine derivatives containing an ester group

Zhu Chun-Rong,Long Jun-Fei,Tang Qian,Gong Cheng-Bin,Fu Xiang-Kai

Abstract This paper aims to develop a multi-colored electrochromic device based on mixed mono- and bi-substituted 4,4′-bipyridine derivatives containing an ester group. A series of these derivatives were synthesized, and their electrochemical and electrochromic properties were studied through cyclic voltammetry and ultraviolet–visible spectroscopy. The mono- and bi-substituted 4,4′-bipyridine derivatives containing an ester group displayed different onset bias and colored state. Mono-substituted 4,4′-bipyridine derivatives showed a magenta colored state at an onset bias of − 1.3 V; bi-substituted 4,4′-bipyridine derivatives showed violet colored states at an onset bias of − 0.8 V. A multi-colored electrochromic device was achieved by mixing mono- and bi-substituted 4,4′-bipyridine derivatives as the electrochromic layer. Graphical Abstract

CAS / MDL: 553-26-4 105-36-2
研究领域: 材料科学 · 电化学
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SYNTHETIC METALS · 2020 · IF 3.286

Star-shaped monosubstituted 2,6-diphenyl-4,4′-bipyridinium salts with good electrochromic switching stability

Song Liu,Zhen-jie Huang,Feng Li,Wei-jing Zhang,Chun-rong Zhu,Cheng-bin Gong,Jun-fei Long,Qian Tang

In this study, a series of novel star-shaped monosubstituted 2,6-diphenyl-4,4′-bipyridinium salts with various alkyl, alkenyl, and aryl groups were designed and synthesized, and their electrochemical, electro-optical, and electrochromic properties were investigated. The electrochromic properties such as different colored states (sky blue versus purple), reasonable contrast, coloration efficiency, and, in particular, the switching stabilities of electrochromic devices based on star-shaped monosubstituted 2,6-diphenyl-4,4′-bipyridinium salts were better than those of devices based on linear monosubstituted pyridinium salts. All the compounds with alkyl, alkenyl, and aryl groups showed good switching stability and the change in the optical contrast after 1000 cycles was small (<5%). However, N-substituents significantly affected the switching stability of electrochromic devices based on linear monosubstituted 4,4′-bipyridine derivatives.

研究领域: 材料科学 · 电化学
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CANADIAN JOURNAL OF CHEMICAL ENGINEERING · 2025 · IF 1.9

Highly selective monosubstitution of symmetrical dialkoxysilanes in continuous flow: Kinetics and mechanisms research

Jiadi Zhou,Shangkun Bai,Weilong Zhang,Bingbing Chen,Yuyu Yang,Qilin Xu,Zhiqun Yu

Monosubstituted symmetrical dialkoxysilanes, intermediates in the production of numerous well-known materials, present challenges for selective monosubstitution due to the presence of two alkoxy groups in similar chemical environments. Notably, kinetic studies on this phenomenon have not been documented. In addressing this knowledge gap, we developed a continuous flow system to the reaction kinetics between diethoxydimethylsilane and vinyl magnesium chloride, enhancing our understanding of these reactions. We initially analyzed the reaction order, pre -exponential factors, and activation energies systematically. The kinetic investigation revealed that the partial reaction order for diethoxydimethylsilane was first-order, the partial reaction order for vinyl magnesium chloride was also first-order, and the overall reaction order was second-order. The activation energy of the main reaction was 39.21 kJ/mol, and the activation energy of the side reaction was 59.72 kJ/mol. Therefore, precise control of the reaction conditions is essential for improving the yield. This kinetic investigation identified a potential reaction mechanism, which was later confirmed through a series of experiments. These experiments accurately determined the applicable concentration and temperature ranges for our kinetic model. Further, simulations of the model assessed the influences of reaction temperature and molar ratios on the monosubstitution selectivity, aiming to achieve controlled reaction outcomes. This study provides new insights into the reaction kinetics of Grignard reagents with symmetrical dialkoxysilanes and offers valuable guidance for optimizing reaction conditions in industrial applications. This study demonstrates selective monosubstitution of symmetrical dialkoxysilanes in a laminar flow reactor. Compared to traditional batch processes, the laminar flow reactor achieved milder conditions and higher selectivity, reaching 99.5% selectivity and 97.9% yield through kinetic studies and model simulations.

CAS / MDL: 78-62-6
研究领域: 化学工程 · 材料科学
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FUEL PROCESSING TECHNOLOGY · 2021 · IF 7.033

Synthesis and comprehensive fuel properties of mono-substituted alkyl adamantanes for advanced aerospace propulsion

Jiawei Xie,Chengxiang Shi,Yunxiao Zhao,Lun Pan,Xiangwen Zhang,Ji-Jun Zou

Design and choice of fuels continue to be improved for aviation propulsion, and alkyl adamantanes have attracted great attention due to their high density, good low-temperature properties and potential characteristics. Herein, we reported a facile route to synthesize mono-substituted alkyl adamantanes via modified Grignard coupling (followed with one-step hydrodeoxygenation), including 1-ethyl-adamantane, 2-ethyl-adamantane, and 1- n -propyl-adamantane with high yields (> 75%). The process was modified via concentrating the Grignard reagents and altering the solvent, and one-step hydrodeoxygenation catalyzed by commercial Pd/C and zeolites was developed. Subsequently, comprehensive characteristics of alkyl diamondoid series, such as oxidation stability and combustion properties , were evaluated using pressure differential scanning calorimetry , rapid small-scale oxidation test, and hot-plate ignition test. Also, the specific impulse of alkyl diamondoids were revealed by theoretical calculation. The high-density alkyl diamondoids present adequate oxidation stability and possess better combustion characteristics over JP-10, thus can be considered as potential high-energy-density fuel for aerospace propulsion .

研究领域: 化学工程 · 能源科学 · 材料科学
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SOLAR ENERGY MATERIALS AND SOLAR CELLS · 2024 · IF 6.3

All-in-one electrochromic devices with high optical contrast based on novel mono-substituted extended viologens

Haibo Wu,Fangyuan Sun,Chengwei Jiang,Fengyu Su,Yanqing Tian,Yan Jun Liu

In this study, three novel monoheptyl-substituted extended viologens ( EDOT-C7 , O-C7 , and BTD-C7 ) were synthesized by introducing ethylenedioxythiophene, furan, and benzothiadiazole moieties between the two pyridine rings as the chromophores, respectively. Their all-in-one ECDs were prepared, which were named ECD-EDOT , ECD-O and ECD-BTD , respectively. The devices’ performance was investigated systematically, including electrochemical properties, photoelectric properties and electrochromic properties. Due to the different electronic properties of the chromophores, the devices exhibited different colored states, including orange ( ECD-EDOT ), magenta ( ECD-O ) and blue-violet ( ECD-BTD ). All the devices exhibit good coloration efficiency of 71.1 cm 2 /C ( ECD-EDOT ), 107.7 cm 2 /C ( ECD-O ) and 91.6 cm 2 /C ( ECD-BTD ). In addition, the devices displayed relatively high optical contrast and cycling stability. The optical contrast of ECD-EDOT , ECD-O and ECD-BTD reached 62.3 %, 71.1 % and 70.0 %, respectively. Among them, ECD-BTD exhibited the most excellent stability, which retains 82.0 % optical contrast of its initial state after continuous 1000 working cycles. Additionally, a variety of multicolor (including blue, black, brown, and red, etc) electrochromic devices based on the synthesized monoheptyl-substituted extended viologen ( O-C7 ) and a reported diheptyl viologen ( DHBP ) have been successfully obtained by the regulation of the molar ratios of the two chosen compounds, which shows the bright application prospect of mono-substituted extended viologen in the multicolor electrochromic field.

CAS / MDL: 90076-65-6 102-54-5
研究领域: 材料科学 · 电化学 · 有机合成
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RSC Advances · 2020 ·Vol. 10 ·期 60 ·36862-36872 · IF 3.119

Functionalization of MOF-5 with mono-substituents: effects on drug delivery behavior

Mengru Cai,Liuying Qin,Longtai You,Yu Yao,Huimin Wu,Zhiqin Zhang,Lu Zhang,Xingbin Yin,Jian Ni

Metal organic frameworks (MOFs) are widely used in drug carrier research due to their tunability. The properties of MOFs can be adjusted through incorporation of mono-substituents to obtain pharmaceutical carriers with excellent properties. In this study, different functional groups of –NH2, –CH3, –Br, –OH and –CH2CH are connected to MOF-5 to analyse the effect of mono-substituent incorporation on drug delivery properties. The resulting MOFs have similar structures, except for Br–MOF. The pore size of this series of MOFs ranges from 1.04 nm to 1.10 nm. Using oridonin (ORI) as a model drug, introduction of the functional groups appears to have a significant effect on the drug delivery performance of the MOFs. The IRMOFs can be ranked according to drug-loading capacity: MOF-5 > HO–MOF-5 > H3C–MOF-5 = Br–MOF-5 > H2N–MOF-5 > CH2CH–MOF-5. The ORI release from ORI @IRMOFs is explored at two different pH values: 7.4 and 5.5, and the ORI@IRMOFs are ranked according to the cumulative release percentage of ORI: ORI@MOF-5 > ORI@Br–MOF-5 > ORI@H3C–MOF-5 > ORI@H2N–MOF-5 > CH2CH–MOF-5 > ORI@ HO–MOF-5. In particular, the release behaviour of ORI@MOFs is described through a new model. The different drug delivery performance of MOFs may be due to the complex interactions between MOFs and ORI. In addition, the introduction of single substituents does not change the biocompatibility of MOFs. MTT in vitro experiments prove that this series of MOFs has low cytotoxicity. This study shows that the incorporation of single substituents can effectively adjust the drug delivery behaviour of MOFs, which is conducive to realization of personalized drug delivery modes. The introduction of active groups can also facilitate post-synthesis modification to achieve coupling of targeting groups. MOFs incorporated with single substituents perform favorably in terms of use as biomedical drug delivery alternative carriers in effective drug payload and flexible drug release.

CAS / MDL: 68-12-2 10196-18-6
研究领域: 材料科学 · 药学 · 生物医学工程
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MACROMOLECULAR CHEMISTRY AND PHYSICS · 2020 ·Vol. 221 ·期 18 ·2000157 · IF 2.335

Synthesis and Characterization of Polyrotaxanes Comprising γ-CDs and Distal Azide-Terminated PHEMA Using Propargylamine Monosubstituted β-CDs as End Stoppers

Ming Gao,Hang Lu,Rong-Hao Song,Lin Ye,Ai-Ying Zhang,Zeng-Guo Feng

To highlight whether γ-cyclodextrins (CDs) facilitate propargylamine monosubstituted β-CDs (PA-β-CDs) as end stoppers to get threaded onto a distal azide terminated poly(2-hydroxyethylmethacrylate) (PHEMA) homopolymer (PH-46-2N 3 ) to create linear and hyperbranched polyrotaxanes (PRs) via the in situ copper-catalyzed azide/alkyne cycloaddition (CuAAC), PH-46-2N 3 is self-assembled with a varying amount of γ-CDs in water and then subjected the CuAAC with PA-β-CDs to end-cap the resulting γ-CD-PHEMA polypseudorotaxanes (PPRs) into the γ-CD-PHEMA PRs. It demonstrates that γ-CDs cannot promote PA-β-CDs to be entrapped on the PHEMA chain most likely due to their different cavity size and molecular framework and linear PRs are always formed with up to 29% γ-CD coverage ratio along the PHEMA axis thereof.

研究领域: 高分子化学 · 超分子化学 · 材料科学
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2024 · IF 3.8

Diels–Alder Reaction of Biofuran Derivatives and Cycloolefin for Directional Synthesis of Fused Ring Hydrocarbon High Density Jet Fuel

Xianlong Liu,Yiting Zhao,Gewei Zhang,Chengxiang Shi,Lun Pan,Xiangwen Zhang,Ji-Jun Zou

Attention has been drawn to the potential of renewable biomass as an alternative to petroleum-based feedstocks for the synthesis of high-density fuels given the depletion of petroleum resources and critical environmental issues. In this study, fused ring high-density liquid fuel precursors were directionally synthesized from biofuran derivatives by the Diels–Alder reaction. The impact of different dienophiles on the Diels–Alder reaction of 2-methylfuran facilitated by zeolites was evaluated. The influences of the catalyst, reaction temperature, and reactant ratio on the reaction were explored. Moreover, this study emphasized the specific synthesis of high density fuels by examining the significant influence of the substrate structure on the Diels–Alder reaction. When preparing polycyclic structures through Diels–Alder reactions of furan derivatives, it is advisible to consider monosubstituted furan derivatives first due to their high electron density and suitable steric resistance. The insights gleaned from this study provide substantial guidance for selecting suitable feedstocks for fuel synthesis, further contributing to sustainable energy solutions.

CAS / MDL: 6482-24-2 110-00-9
研究领域: 化学工程 · 有机化学 · 可持续能源 · 燃料科学
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JOURNAL OF MEDICINAL CHEMISTRY · 2024 · IF 6.8

Rational Design of Mono-Substituted Gd-DOTA as Highly Stable and Efficient MRI Contrast Agents for Hepatobiliary and Inflammation Imaging

Yinghui Ding,Xinzhong Ruan,Kun Shu,Weiyuan Xu,Yao Liu,Gengshen Mo,Jiao Xu,Yong Jian,Jilai Zhang,Lingfeng Zhang,Keren Wang,Ji-Ting Hou,Jianliang Shen,Zhihan Yan,Fangfu Ye,Jiang Zhu,Lixiong Dai

Hepatobiliary-specific magnetic resonance imaging contrast agents (MRI CAs) play a crucial role in the early diagnosis of hepatocellular carcinoma (HCC). However, only two acyclic CAs, Gd-BOPTA and Gd-EOB-DTPA, exhibit unfavorable kinetic inertness. Our study focused on the development of superior stable innovative macrocyclic CAs. By introducing a lipophilic benzyloxy group (OBn) into the H4DOTA ring (Gd-L1), we achieved significant enhancement in kinetic inertness. In vivo experiments in mice demonstrated that 40% of the dosage was distributed to the liver at 5 min, providing sustained hepatic enhancement for over 35 min. We also developed an MPO-responsive MRI CA (Gd-L3), which can participate in the “peroxidase cycle” as the substrate, generating oligomers with a 3.8-fold increase in relaxivity, and selectively enhance the lesion in an acute gout mouse model. Overall, our work represents a significant advancement in the field of hepatic and inflammatory MRI, offering promising avenues for early diagnosis and improved imaging outcomes.

CAS / MDL: 7087-68-5 105-36-2
研究领域: 医学成像 · 药物化学 · 分子生物学
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POLYMER · 2023 · IF 4.6

Synthesis of parallel double stranded polyrotaxanes comprising γ-CDs and distal azido-terminated PEG via Click reaction using propargylamine monosubstituted β-CDs as end stoppers

Ming Gao,Chun-jiang He,Xue Geng,Lin Ye,Ai-ying Zhang,Zeng-guo Feng

When γ-CDs were self-assembled with a distal 2-chloropropionyl terminated poly (ethylene glycol) (PEG-2Cl) in aqueous solution, two distinct polypseudorotaxanes (PPRs), a single stranded one and a double stranded one were identified from the upper clear solution and the lower precipitates, respectively. Moreover, if the chlorine groups in PEG-2Cl were converted into the azido groups to give a bifunctional azido terminated PEG (PEG-2N 3 ) and then subjected to the inclusion complexation with γ-CDs, two similar double stranded PPRs were lyophilized from the upper and lower layer products. To probe whether the parallel or bent double stranded PPRs were created from the self-assembly of γ-CDs with PEG-2N 3 , the in situ copper-catalyzed azide/alkyne cycloaddition (CuAAC) was conducted to transform the resulting PPRs into the PRs using propargylamine monosubstituted β-CDs (PA-β-CDs) as bulky stoppers. After thorough purification, both the upper and lower layer products lyophilized therefrom were revealed the same parallel double stranded PRs by spectral and thermal analyses.

研究领域: 材料科学 · 聚合物化学 · 超分子化学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2018 · IF 3.927

1,3,5-Triazine tetrad-aza cyclophanes coated silica as a novel stationary phase for high performance liquid chromatography

Wenfen Zhang,Fei Wang,Yanhao Zhang,Wuduo Zhao,Yi Guo,Wei Wen,Shusheng Zhang

A new stationary phase (TTCPSP) has been prepared by covalently bonding 1,3,5-triazine tetrad-aza cyclophanes (TTCP) onto silica gel using 3-aminopropyl triethoxysilane as the coupling reagent. The stationary phase developed in this way was characterized by IR spectroscopy, elemental analysis and thermogravimetric analysis. The chromatographic performance and retention mechanisms of the new stationary phase were validated and compared with octadecylsilyl (ODS) stationary phases using a variety of compounds including monosubstituted benzenes, polycyclic aromatic hydrocarbons (PAHs) and flavonoids. The results indicate that the 1,3,5-triazine tetrad-aza cyclophanes (TTCPSP) stationary phase addresses solutes with multiple interactions, such as hydrophobic, hydrogen bonding, π-π, and inclusion interactions. TTCPSP, which shows strong retention ability to compounds containing OH, NH 2 or phenyl conjugate groups, is promising as a type of solid phase extraction sorbent.

研究领域: 分析化学 · 色谱学
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