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Symmetry breaking of highly symmetrical nanoclusters for triggering highly optical activity

Fundamental Research 2024年第1期4卷 63-68页

作者： Xiao Wei Hao Li Honglei Shen Chuanjun Zhou Shuxin Wang Xi Kang Manzhou Zhu Department of Chemistry and Centre for Atomic Engineering of Advanced Materials Key Laboratory of Structure and Functional Regulation of Hybrid Materials of Ministry of EducationInstitutes of Physical Science and Information Technology and Anhui Province Key Laboratory of Chemistry for Inorganic/Organic Hybrid Functionalized Materials.Anhui UniversityHefei 230601China

Developing new approaches to fulfill the enantioseparation of nanocluster racemates and construct cluster-based nanomaterials with optical activity remains highly desired in cluster science,because it is an essential prerequisite for fundamental research and extensive applications of these nanomaterials.We herein propose a strategy termed“active-site exposing and partly re-protecting”to trigger the symmetry breaking of highly symmetrical nanoclusters and to render cluster crystals optically active.The vertex PPh_(3)of the symmetrical Ag_(29)(SSR)_(12)(PPh_(3))_(4)(SSR=1,3-benzenedithiol)nanocluster was firstly dissociated in the presence of counterions with large steric hindrance,and then the exposed Ag active sites of the obtained Ag_(29)(SSR)_(12)nanocluster were partly re-protected by Ag^(+),yielding an Ag_(29)(SSR)_(12)-Ag_(2)nanocluster with a symmetry-breaking construction.Ag_(29)(SSR)_(12)-Ag_(2)followed a chiral crystallization mode,and its crystal displayed strong optical activity,derived from CD and CPL characterizations.Overall,this work presents a new approach(i.e.,active-site exposing and partly re-protecting)for the symmetry breaking of highly symmetrical nanoclusters,the enantioseparation of nanocluster racemates,and the achievement of highly optical activity.

关键词： Atomically precise nanocluster Symmetry breaking enantioseparation Circularly polarized luminescent Photoluminescence

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A chiral metal-organic framework{(HQA)(ZnCl_(2))(2.5H_(2)O)}n for the enantioseparation of chiral amino acids and drugs

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Journal of Pharmaceutical Analysis 2023年第4期13卷 421-429页

作者： Xiangtai Zheng Qi Zhang Qianjie Ma Xinyu Li Liang Zhao Xiaodong Sun Shanghai Engineering Research Center of Organ Repair School of MedicineShanghai UniversityShanghai200444China School of Pharmacy Jiangsu UniversityZhenjiangJiangsu212013China Department of Pharmacy Shanghai Baoshan Luodian HospitalShanghai201908China Luodian Clinical Drug Research Center Institute for Translational Medicine ResearchShanghai UniversityShanghai200444China

Chiral metal-organic frameworks(CMOFs)with enantiomeric subunits have been employed in chiral chemistry.In this study,a CMOF formed from 6-methoxyl-(8S,9R)-cinchonan-9-ol-3-carboxylic acid(HQA)and ZnCl_(2),{(HQA)(ZnCl_(2))(2.5H_(2)O)}n,was constructed as a chiral stationary phase(CSP)via an in situ fabrication approach and used for chiral amino acid and drug analyses for the first time.The{(HQA)(ZnCl_(2))(2.5H_(2)O)}n nanocrystal and the corresponding chiral stationary phase were systematically characterised using a series of analytical techniques including scanning electron microscopy,X-ray diffraction,Fourier transform infrared spectroscopy,circular dichroism,X-ray photoelectron spectroscopy,thermogravimetric analysis,and Brunauer-Emmett-Teller surface area measurements.In opentubular capillary electrochromatography(CEC),the novel chiral column exhibited strong and broad enantioselectivity toward a variety of chiral analytes,including 19 racemic dansyl amino acids and several model chiral drugs(both acidic and basic).The chiral CEC conditions were optimised,and the enantioseparation mechanisms are discussed.This study not only introduces a new high-efficiency member of the MOF-type CSP family but also demonstrates the potential of improving the enantioselectivities of traditional chiral recognition reagents by fully using the inherent characteristics of porous organic frameworks.

关键词： Capillary electrochromatography Metal-organic framework enantioseparation Chiral stationary phase Open-tubular column Dansyl amino acids

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enantioseparation of 3-chlorophenylglycine enantiomers using Mandyphos-Pd as chiral extractant

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Chinese Journal of Chemical Engineering 2021年第5期34卷 96-103页

作者： Xiong Liu Shuhuan Chen Yu Ma Wenjie Xiao School of Chemistry and Chemical Engineering Hunan University of Science and TechnologyXiangtan 411201China Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers Xiangtan 411201China

Chiral extractant plays a key role in chiral extraction,and considerable efforts have been undertaken for the development of new and efficient chiral extractants in recent years.This work demonstrated for the first time that chiral ferrocenyl diphosphine ligand(Mandyphos-Pd)had considerable ability to enantioseparate 3-Chlorophenylglycine enantiomers with separation factor(α)of 2.64.Mandyphos-Pd concentration and pH had significant influences on enantioselectivity,while operating temperature showed less influence.The extraction experiments can be performed at room temperature(20℃)which had the advantage of energy saving.After optimization,the highest performance factor(pf,0.08376)was obtained at the condition of pH 7.8 and Mandyphos-Pd concentration 1.2 mmol·L^(-1).According to the experimental results,the possible recognition mechanism was discussed.

关键词： enantioseparation Mandyphos 3-Chlorophenylglycine Response surface method Recognition mechanism

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Chiral phenethylamine synergistic tricarboxylic acid modified β-cyclodextrin immobilized on porous silica for enantioseparation

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Chinese Chemical Letters 2023年第3期34卷 162-165页

作者： Hui Li Xiaoping Wang Chengxiang Shi Liang Zhao Zuguang Li Hongdeng Qiu CAS Key Laboratory of Chemistry of Northwestern Plant Resources and Key Laboratory for Natural Medicine of Gansu Province Lanzhou Institute of Chemical PhysicsChinese Academy of SciencesLanzhou 730000China College of Chemical Engineering Zhejiang University of TechnologyHangzhou 310014China

In this work, a series of chiral phenethylamine synergistic tricarboxylic acid modified β-cyclodextrin bonded stationary phase for high performance liquid chromatography(HPLC) were synthesized via a simple one-pot synthesis approach. Various racemates(aryl alcohols, flavanones, triazoles, benzoin, etc.) were well separated on the tricarboxylic acid modified chiral stationary phases in both normal and reversed modes with good reproducibility and stability, and the influence of mobile phase composition on resolution(R_(s)) were deeply investigated. The RSD values of Rsfor repeatability and column-to-column were below 1.28% and 3.05%, respectively. Hence, the fabrication of tricarboxylic acid modified chiral stationary phase(CSPs) is a new efficient strategy to improve the application of β-cyclodextrin as CSPs in the field of chromatography.

关键词： Tricarboxylic acid β-cyclodextrin Chiral stationary phases enantioseparation One-pot strategy

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enantioseparation by HPLC Using an Inorganic Chiral Mesoporous Silica with Highly-ordered Structure

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Chemical Research in Chinese Universities 2019年第6期35卷 978-982页

作者： PENG Bo FU Shiguo LI Yanxia ZHANG Junhui XIE Shengming LI Li LYU Yun DU AN Aihong CHEN Xuexian YUAN Liming Department of Chemistry Yunnan Normal UniversityKunming 650500P.R.China

Highly-ordered inorganic chiral mesoporous silica(HOCMS)has attracted substantial interest in recent decades.High performance liquid chromatography(HPLC)is the most important approach for the separation of enantiomers and herein reported an HPLC chiral stationary phase composed of HOCMS.The column was fabricated by conventional high pressure slurry packing.Eighteen racemates,including alcohols,ketones,amines,aldehydes and organic acids,were resolved on the column.Good chiral separations of hydrobenzoin,metoprolol,propranolol hydrochloride,4-methyl-2-pentanol,omeprazole,2,2′-furoin and ketoprofen were obtained.The relative standard devi-ations for five replicate separations of racemates were 0.1%–0.16%for retention time and 1.73%–2.64%for peak areas.The results suggest that HOCMS is a promising candidate for preparation of chiral stationary phases for HPLC.

关键词： Highly-ordered inorganic chiral mesoporous silica Chiral stationary phase High performance liquid chromatography enantioseparation

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enantioseparation of some Racemic Compounds on Cellulose Tris (3,5-dimethylphenylcarbamate) Chiral Stationary Phase

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Chinese Chemical Letters 2000年第8期11卷 731-734页

作者： Xiao Qian HAN Hui Tao LIU Jin Zhang GAO Jing Guo HOU Chong Yang LI Guo Hu ZHAO Institute of Chemistry Northwest Normal UniversityLanzhou 730070 Institute of Chemistry Lanzhou UniversityLanzhou 730000

Seven chiral compounds were resolved on cellulose tris (3,5-dimethylphenylcarbamate) chiral stationary phase (CDMPC-CSP) using n-hexane/alcohol as mobile phase. Solvent strength and structural characteristics of the c... 详细信息

关键词： enantioseparation cellulose-based chiral stationary phase racemic compounds HPLC

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enantioseparation of Aminoglutethimide by High-speed Countercurrent Chromatography Using Carboxymethly-β-cyclodextrin as Chiral Selector

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Chinese Chemical Letters 2006年第6期17卷 787-790页

作者： Ping AI Jia Chuan LIU Min ZI Zhi Hua DENG Zhi Hong YAN Li Ming YUAN Department of Chemistry Yunnan Normal University Kunming 650092

enantioseparation of aminoglutethimide was performed by high-speed counter-current chromatography with a two-phase system composed of ethyl acetate： methanol： water = 10： 1： 9. The lower phase contained 20 mmol/L of carboxymethly-β-cyclodextrin as chiral selector. The enantiomers were separated in 1.2 h and identified by chiral HPLC. This method was very efficient for the chiral preparative separation.

关键词： High speed countercurrent chromatography enantioseparation aminoglutethimide,carboxymethly-β-cyclodextrin.

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enantioseparation of Dencichine and D-Isomer on L-Cysteine Derivative Phase by Ligand-exchange Chromatography

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Chinese Chemical Letters 2006年第6期17卷 807-808页

作者： Yan Shun MA Qing Hua MENG Hong Yu SHI Yuan De LONG Tian Bao HUANG Chengdu Institute of Organic Chemistry Chinese Academy of Sciences Chengdu 610041 Graduate School of the Chinese Academy of Sciences Beijing 100049

The enantioseparation of dencichine and its D-isomer was achieved on a novel chiral stationary phase via coating N-（2-hydroxyl-3-octoxyl） propyl-S-benzyl-（L）-cysteine on YWG-C18 phase by ligand exchange chromatogr... 详细信息

关键词： Dencichine enantioseparation ligand exchange chromatography chiral stationaryphase.

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Simultaneous enantioseparation and simulation studies of atenolol,metoprolol and propranolol on Chiralpak^■IG column using supercritical fluid chromatography

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Journal of Pharmaceutical Analysis 2021年第6期11卷 746-756页

作者： Pranav A.Pandya Priyanka A.Shah Pranav S.Shrivastav Department of Chemistry School of SciencesGujarat UniversityAhmedabad380009India

enantioseparation of threeβ-blockers,i.e.,atenolol,metoprolol and propranolol,was studied on amylose tris(3-chloro-5-methylphenylcarbamate)immobilized chiral stationary phase using supercritical fluid chromatography(SFC).The effect of organic modifiers(methanol,isopropanol and their mixture),column temperature and back pressure on chiral separation ofβ-blockers was evaluated.Optimum chromatographic separation with respect to resolution,retention,and analysis time was achieved using a mixture of CO_(2) and 0.1%isopropyl amine in isopropanol:methanol(50:50,V/V),in 75:25(V/V)ratio.Under the optimized conditions,the resolution factors(Rs)and separation factors(a)were greater than3.0 and 1.5,respectively.Further,with increase in temperature(25-45℃)and pressure(100-150 bars)there was corresponding decrease in retention factors(k),a and Rs.However,a reverse trend(a and Rs)was observed for atenolol with increase in temperature.The thermodynamic data from van’t Hoff plots revealed that the enantioseparation was enthalpy driven for metoprolol and propranolol while entropy driven for atenolol.To understand the mechanism of chiral recognition and the elution behavior of the enantiomers,molecular docking studies were performed.The binding energies obtained from simulation studies were in good agreement with the elution order found experimentally and also with the free energy values.The method was validated in the concentration range of 0.5-10μg/m L for all the enantiomers.The limit of detection and limit of quantitation ranged from 0.126 to 0.137μg/m L and 0.376-0.414μg/m L,respectively.The method was used successfully to analyze these drugs in pharmaceutical preparations.

关键词： enantioseparation Supercritical fluid chromatography β-blockers Chiralpak^(■)IG column Molecular docking Binding energy

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enantioseparation of Novel Chiral Tetrahedral Clusters on a Chiral Stationary Phase (CSP) by High Performance Liquid Chromatography

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色谱 2004年第4期22卷 329-330页

作者： WANG Xia~1, LI Wenzhi~2, LIU Chunhui~1, CHEN Liren~1, LI Yongmin~1(1. Lanzhou Institute of Chemical Physics, The Chinese Academy of Sciences, Lanzhou 730000, China 2. Chemistry and Chemical Engineer College, Liaocheng University, Liaocheng 252059, China ) Lanzhou Institute of Chemical Physics The Chinese Academy of Sciences Lanzhou 730000 Chemistry and Chemical Engineer College Liaocheng University Liaocheng 252059

In recent years, the synthesis of chiral tetrahedral clusters has been studied extensively and various types are accessible[1,2], which are a kind of organometallic compounds with greatly growing interest due to their potential application to asymmetric reaction catalysts[3,4]. As an efficient separation technique for enantioseparation which requires mild separation conditions, high performance liquid chromatography (HPLC) is considered to be the most efficient way to resolve the clusters with new-type chiral stationary phases (CSPs) without destruction of the clusters. In the present work, a new CSP was prepared by coating amylose tris(3,5-dimethylphenylcarbamate) (ADMPC) on small particle silica gel, and for the first time applied to the enantioseparation of some new chiral tetrahedral clusters with good results. The effects of various parameters on the retention factors and separation results were also investigated.

关键词： high performance liquid chromatography chiral stationary phase chiral tetrahedral clusters enantioseparation

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