APPLIED ORGANOMETALLIC CHEMISTRY
·
2014
·Vol. 28
·期 11
·814-817
·
IF 2.017
Dongsheng Bai,Guangjian Wang,Fang Ma,Juangang Wang,Kuai Wang,Zijing Yang
Synthesis of cyclic carbonates from CO 2 and terminal epoxides catalyzed by Mg, Ca and In BINOL complexes was achieved without organic solvents. Effects of temperature, CO 2 pressure, reaction time and co-catalyst on the cycloaddition were investigated. Propylene carbonate was obtained under a CO 2 pressure of 1.2 MPa within 10 hours in a yield of 98% catalyzed by Ca–BINOL at 120°C. The order of catalytic activity of the metal center is Ca > In > Mg. Copyright © 2014 John Wiley & Sons, Ltd.
研究领域:
化学
·
材料科学
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DOI
高影响因子
INORGANIC CHEMISTRY
·
2015
·
IF 4.762
Mingtai Sun,Huan Yu,Huihui Li,Hongda Xu,Dejian Huang,Suhua Wang
A weakly fluorescent complex derived from a binaphthol–benzimidazole ligand was designed and synthesized for hydrogen sulfide at different pH conditions. It was demonstrated that the probe showed the same reactivity to various hydrogen sulfide species in a broad range of pH values to generate highly fluorescent product through a displacement reaction mechanism, whereas the product’s fluorescence spectrum exhibited a hypsochromic shift of ∼73 nm (2393 cm–1) as pH increased from neutral to basic, which can be used for distinguishing the various species of hydrogen sulfide. This turn-on fluorescence probe was highly selective and sensitive to hydrogen sulfide with a detection limit of 0.11 μM. It was then applied for evaluating the total content of sulfide (including hydrogen sulfide, hydrosulfide, and sulfide) as well as for the visual detection of gaseous H2S in air using a simple test paper strip.
研究领域:
分析化学
·
生物化学
·
环境科学
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PubMed
高影响因子
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
·
2024
·Vol. 25
·期 11
·5606
·
IF 4.9
Rong Wang,Kaiyue Song,Zhaoqin Wei,Yue Sun,Xiaoxia Sun,Yu Hu
The chiral H8-BINOL derivatives R-1and R-2were efficiently synthesized via a Suzuki coupling reaction, and they can be used as novel dialdehyde fluorescent probes for the enantioselective recognition of R/S-2-amino-1-phenylethanol. In addition, R-1is much more effective than R-2. Scanning electron microscope images and X-ray analyses show that R-1can form supramolecular vesicles through the self-assembly effect of the π-π force and strong hydrogen bonding. As determined via analysis, the fluorescence of the probe was significantly enhanced by mixing a small amount of S-2-amino-1-phenylethanol into R-1, with a redshift of 38 nm, whereas no significant fluorescence response was observed in R-2-amino-1-phenylethanol. The enantioselective identification of S-2-amino-1-phenylethanol by the probe R-1was further investigated through nuclear magnetic titration and fluorescence kinetic experiments and DFT calculations. The results showed that this mechanism was not only a simple reactive probe but also realized object recognition through an ICT mechanism. As the intramolecular hydrogen bond activated the carbonyl group on the probe R-1, the carbonyl carbon atom became positively charged. As a strong nucleophile, the amino group of S-2-amino-1-phenylethanol first transferred the amino electrons to a carbonyl carbocation, resulting in a significantly enhanced fluorescence of the probe R-1and a 38 nm redshift. Similarly, S-2-amino-1-phenylethanol alone caused severe damage to the self-assembled vesicle structure of the probe molecule itself due to its spatial structure, which made R-1highly enantioselective towards it.
研究领域:
超分子化学
·
有机化学
·
分析化学
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PubMed
高影响因子
RSC Advances
·
2022
·Vol. 12
·期 19
·11967-11973
·
IF 4.036
Yafeng Zhang,Huizhen Wang,Hu Yu,Xiaoxia Sun
Phenylalanine an essential aromatic amino acid for humans and animals, cannot be synthesized by humans and animals on their own. However, it synthesizes important neurotransmitters and hormones in the body and is involved in gluconeogenesis and lipid metabolism. Moreover, the two opposite configurations of phenylalanine have different activities. For example, L-phenylalanine is a biologically active optical isomer involved in crucial biological processes, the lack of which will lead to intellectual disability, while D-phenylalanine only acts as a chiral intermediate. In this research, an H8-BINOL chiral fluorescent sensor modified with 1,2,3-triazole was synthesized in high yield (95%) by nucleophilic substitution and click reaction. The chiral fluorescent sensor showed high enantioselectivity toward phenylalanine. L-Phenylalanine enhanced the fluorescence response of the probe significantly, while D-phenylalanine had no obvious fluorescence response change. The enantioselective fluorescence enhancement ratio [ef = (IL − I0)/(ID − I0), where I0 is the fluorescence of the sensor without amino acids] for the highest fluorescence intensity at 20.0 equivalents of amino acids was 104.48. In this way, the probe could be used to identify and differentiate different configurations of phenylalanine.
研究领域:
生物化学
·
分析化学
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DOI
高影响因子
INORGANIC CHEMISTRY COMMUNICATIONS
·
2021
·
IF 2.495
Haijuan Gao,Dongxu Cui,Junning Kou,Honglei Zhao,Chunyi Sun,Xinlong Wang,Zhongmin Su
Herein, we reported a pair of di-nuclear europium enantiomers [Eu 2 (PO 4 ) 6 (R-/S-HL) 6 (MeOH) 4 ]•2MeOH (R-complex( 1a ) and S-complex( 1b )) constructed from chiral ligands (R)-/(S)-(+)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate (R-/S-HL) and europium (III) nitrate by solvothermal method. The structure of the complexes was characterized by single-crystal X-ray diffraction, powder X-ray diffraction and Fourier transform infrared spectroscopy. It was found that R-complex( 1a ) and S-complex( 1b ) were chiral enantiomers with a zero-dimensional chiral cluster structure. The circular dichroism studies further revealed the chiral properties of R-complex( 1a ) and S-complex( 1b ). Moreover, fluorescence sensing tests demonstrated that R-complex( 1a ) and S-complex( 1b ) possessed high enantioselectivity for axially chiral BINOL racemates.
研究领域:
无机化学
·
材料科学
·
分析化学
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产品关联
DOI
高影响因子
ACS Applied Bio Materials
·
2025
·
IF 4.7
Huixiang Wu,Hua Yang,Yiwei Sun,Xingwen Gong,Jianying Huang
Antibiotic resistance has become one of the most pressing global public health concerns. Therefore, the development of effective chiral antibacterial agents capable of simultaneously inhibiting multiple enzymes and specifically interacting with biological targets is a critical and urgent priority. In this study, halogenated chiral BINOL derivatives were designed, synthesized, and characterized, followed by evaluation of their antibacterial activities. Results showed that (S)-6,6′-dibromo-BINOL (S4) exhibited the strongest antibacterial activity against Staphylococcus aureus ATCC 6538 with a minimum inhibitory concentration (MIC) of 2.0 μg/mL and against methicillin-resistant S. aureus (MRSA) ATCC 43,300 with a MIC of 8 μg/mL. Biofilm adhesion of both S. aureus and MRSA was significantly reduced after S4 treatment compared to the parent chiral BINOL (S0). Furthermore, complete bacterial killing of S. aureus and MRSA bacteria was achieved within 12 h at 2MIC of S4. The results also indicated that S-configured BINOL derivatives possess superior antibacterial potency compared to their R-configured counterparts. Multitarget docking analysis further revealed that S4 can strongly bind to key virulence-related targets, including thymidylate kinase (TMK), Pseudomonas aeruginosa quorum-sensing receptor (PqsR), and penicillin-binding protein 2a (PBP2a). These findings confirm that both the stereochemistry and the presence of halogen atoms in these chiral molecules play crucial roles in modulating their antibacterial activities.
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PubMed
高影响因子
APPLIED ORGANOMETALLIC CHEMISTRY
·
2013
·Vol. 27
·期 6
·337-340
·
IF 2.011
Junyu Dong,Tianbin Li,Chuan Dai,Wen Weng,Xinghua Xue,Yuyu Zhang,Qingle Zeng
A straightforward, protecting-group-free protocol for the synthesis of chiral 6-substituted and 6,6’-disubstituted binols (binol = 1,1’-bi-2-naphthol) by palladium-catalyzed hydroxylation, C–N and C–O coupling of chiral 6-bromo- and 6,6’ -dibromo-1,1’-binaphthols is developed. The protecting group free palladium-catalyzed hydroxylation, C–O and C–N cross-coupling protocol affords a straightforward and general method for the synthesis of chiral 6-substituted and 6,6’-disubstituted binols with good yields, avoiding the tedious procedures of introduction and removal of protecting groups. Copyright © 2013 John Wiley & Sons, Ltd.
研究领域:
有机化学
·
合成化学
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DOI
高影响因子
Advanced Optical Materials
·
2024
·Vol. 12
·期 20
·2400379
·
IF 8
Huimin Duan,Jinbiao Zhao,Shuli Li,Dongming Qi,Jiawei Li
Supramolecular polymers with circularly polarized luminescence (CPL) have promoted future intelligence development of polymer-based materials for flexible display. However, preparing polymer-based CPL materials with simultaneous enhanced luminescence dissymmetry factor (| g lum |) and mechanical performance for industrial applications remains challenging. This work develops an eco-friendly preparation method for preparing CPL elastomers from supramolecular polyurethanes bearing chiral fluorescent S (or R)-1,1′-Bi(2-naphthol) (BINOL) groups in a solvent-free system. Surprisingly, a polymer system containing 0.0028 mol% of chiral BINOL unit is sufficient to emit the significant CPL-activity with a | g lum | value of 2.30 × 10 −2 , appear a good mechanical toughness of 56.28 ± 3.9 MJ·m −3 , thereby exhibit multiple flexible anti-counterfeiting behaviors. The long-range ordered microphase arrangement in polyurethanes is the key to improving both mechanical properties and | g lum |. This is attributed to in-situ additive polymerization of BINOL-based isocyanate prepolymer and macromolecular polyols induced helical supramolecular structure, afforded solid-state films with flexibility and chiral amplification. Furthermore, these results from Circular dichroism, CPL, Fourier transform infrared, X-ray diffraction analyses, and atomic force microscope confirm the formation of long-range ordered microphase arrangement through the synergistic effect of hydrogen bonding and π–π interactions. This work offers significant insights into the construction of CPL elastomers for developing novel flexible display materials.
研究领域:
材料科学
·
光学
·
高分子化学
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产品关联
DOI
高影响因子
CHIRALITY
·
2017
·Vol. 29
·期 7
·340-347
·
IF 1.956
Hongxing Dong,Danxia Zhang,Hailong Lin,Yudan Wang,Lijia Liu,Meixia Zheng,Xiaobo Li,Chunhong Zhang,Junqing Li,Peng Zhang,Juhyok So
Acrylamide (AM) was copolymerized with ethylene glycol dimethacrylate (EGDMA) in the presence of ( R )-1,1′-binaphthalene-2-naphthol (BINOL) as the template molecules on the surface of silica gel by a free radical polymerization to produce a chiral stationary phase based on the surface molecularly imprinted polymer (SMIP-CSP). The SMIP-CSP showed a much better separation factor ( α = 4.28) than the CSP based on the molecularly imprinted polymer (MIP-CSP) without coating on the silica gel ( α = 1.96) during the chiral separation of BINOL enantiomers by high-performance liquid chromatography. The influence of the pretreatment temperature and the content of the template molecule (( R )-BINOL) of the SMIP-CSP, and the mobile phase composition on the separation of the racemic BINOL were systematically investigated.
研究领域:
分析化学
·
材料科学
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产品关联
DOI
PubMed
高影响因子
DYES AND PIGMENTS
·
2022
·
IF 5.122
Chunfang Liu,Chunming Yuan,Guangjin Shi,Ke Jia,Jing Liu,Kun-Peng Wang,Shaojin Chen,Zhi-Qiang Hu
Chiral organic fluorescent materials have attracted broad attention for their application in various chiroptical devices. Helicenes possess special helical structure and unique optical properties , and have been utilized to develop chiral organic fluorescent materials with excellent chiroptical performance. However, the low luminescence efficiency of helicene-based chiral fluorescent materials in solid state limits their practical applications. In this work, chiral organic fluorescent emitters with helicene moiety have been developed from binaphthanol structure. These BINOL [4]helicene compounds display aggregation-enhanced emission properties, and have strong blue emission in solid state with fluorescent quantum yield up to 0.67. The DFT calculation reveals that these compounds have highly twisted molecular structures. Thus, the excellent fluorescent properties in solid state could be aroused by the highly contorted molecular structures, which could limit the π-π stacking of adjacent molecules in solid state. The enantiomers of these compounds show strong Cotton effects in circular dichroism spectra, and the molecules with 4-methoxy phenyl moiety exhibit circularly polarized luminescence properties .
研究领域:
化学
·
光学材料
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DOI
高影响因子
DYES AND PIGMENTS
·
2023
·
IF 4.5
Fangxiu Li,Yue Sun,Xiaoxia Sun,Yu Hu,Yanli Wu
Due to the hydrophilicity of furan ring and hydroxyl group, and hydrophobicity of benzene ring and cyclohexyl group, the compounds are easy to form hydrophilic and hydrophobic amphoteric vesicles through self-assembly. The self-assembled vesicles were designed and facilely synthesized using the 2-furanboronic acid and H 8 -BINOL by Suzuki coupling reaction, which could serve as a novel probe with high enantioselectivity for D/L-Phe. In SEM and TEM images, after adding the L-Phe, the vesicle structure of the H 8 -BINOL derivatives changed from spherical to dendritic nanotube structures. On the contrary, after the addition of D-Phe, the spherical vesicle structure changed only slightly, indicating that the material had specific recognition for L-Phe. Moreover, the new fluorescent probes had unique rigid structures and obvious enantioselective recognition for phenylalanine in fluorescence testes. In the methanol solution, after adding the L-Phe, the fluorescence intensity of R - 1 and S - 1 decreased significantly at 368 nm and increased at 306 nm, but D-Phe had no obvious fluorescence effect on the probes, which indicated that the fluorescent probes had a good guiding effect on the recognition of amino acids by chiral compounds.
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高影响因子
ACS Applied Materials & Interfaces
·
2024
·
IF 8.3
Rong Wang,Kaiyue Song,Lixue Yang,Yue Sun,Xiaoxia Sun,Yu Hu
R-BTOBD exhibited significant aggregation-induced Emission (AIE) characteristics, including high brightness (αAIE ≈ 40), robust light stability, a substantial Stokes shift (128 nm), and a high signal-to-noise ratio, effectively overcoming aggregation-caused quenching (ACQ). Derived from the axially chiral R-H8–BINOL, R-BTOBD was synthesized via nucleophilic cyclization and exhibited pronounced self-assembly properties. Through robust intra- and intermolecular hydrogen bonding interactions, R-BTOBD formed diverse supramolecular structures, including spherical flower-like aggregates, hollow-core triangular tubules, hexagonal tubules, and irregular white block-like stacks. The specific morphology was influenced by factors such as solvent and pH. For fluorescence applications, R-BTOBD can be employed as an effective visual pH detector through an AIE-enhanced excited-state intramolecular proton transfer (AIE-ESIPT) mechanism. When incorporated into pH paper, it exhibited a bright yellow fluorescence across a wide pH range (pH 1–11), transitioning to an intense bright blue fluorescence under strongly basic conditions (pH 12–14). In chiral applications, R-BTOBD demonstrated potential as a chiral switching agent, leveraging the pronounced changes and inversions in its circular dichroism (CD) signals under varying aggregation states and pH conditions. Additionally, it serves as a specific chiral enantioselective fluorescence probe for l-lysine, demonstrating high efficiency and a low detection limit. Given its exceptional fluorescence and chiral properties, this fluorescent material has significant potential for diverse applications in fluorescence, chirality, and visual inspection.
研究领域:
材料科学
·
分析化学
·
生物化学
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DOI
PubMed
高影响因子
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