3,237 results match your criteria series chiral


Redox deracemization of phosphonate-substituted dihydropyrimidines.

Org Biomol Chem 2021 Dec 2. Epub 2021 Dec 2.

School of Chemical Engineering, Dalian University of Technology, Dalian 116024, P. R. China.

An efficient redox deracemization of the phosphonic ester substituted 3,4-dihydropyrimidin-2-one (DHPM) derivatives is described. The one-pot deracemization strategy consisted of the oxidization to destroy the stereocenter center and the following asymmetric transfer hydrogenation to regenerate the chiral carbon center with the vicinal phosphonic ester group, providing a series of optically active phosphonate substituted DHPMs with up to 96% ee. Read More

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December 2021

Palladium-Catalyzed Asymmetric Cross-Coupling Reactions of Cyclobutanols and Unactivated Olefins.

Org Lett 2021 Dec 1. Epub 2021 Dec 1.

Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai 200438, P. R. China.

Transition-metal-catalyzed activations of carbon-carbons bonds of small strained rings have widespread applications in synthetic and medicinal chemistry. However, coupling reactions of cyclobutanols involving β-carbon elimination to construct C(sp)-C(sp) bonds have scarcely been developed. Here, we demonstrate a highly enantioselective Pd-catalyzed intermolecular C(sp)-C(sp) coupling reaction of a broad range of cyclobutanol derivatives and unactivated alkenes, allowing convenient access to a series of chiral benzene-fused cyclic compounds in a highly regio-, chemo-, and enantioselective manner. Read More

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December 2021

Synthesis and characterization of chiral 6-azaspiro[2.5]octanes as potent and selective antagonists of the M muscarinic acetylcholine receptor.

Bioorg Med Chem Lett 2021 Nov 24;56:128479. Epub 2021 Nov 24.

Warren Center for Neuroscience Drug Discovery, Vanderbilt University Medical Center, Nashville, TN 37232, United States; Department of Pharmacology, Vanderbilt University Medical Center, Nashville, TN 37232, United States; Department of Chemistry, Vanderbilt University Medical Center, Nashville, TN 37232, United States; Department of Biochemistry, Vanderbilt University Medical Center, Nashville, TN 37232, United States. Electronic address:

In this manuscript, we report a series of chiral 6-azaspiro[2.5]octanes and related spirocycles as highly potent and selective antagonists of the muscarinic acetylcholine receptor subtype 4 (mAChR). Chiral separation and subsequent X-ray crystallographic analysis of early generation analogs revealed the R enantiomer to possess excellent human and rat M potency, and further structure-activity relationship (SAR) studies on this chiral scaffold led to the discovery of VU6015241 (compound 19). Read More

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November 2021

Chiral Aminoalcohols and Squaric Acid Amides as Ligands for Asymmetric Borane Reduction of Ketones: Insight to In Situ Formed Catalytic System by DOSY and Multinuclear NMR Experiments.

Molecules 2021 Nov 14;26(22). Epub 2021 Nov 14.

Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Bl. 9, Acad. G. Bonchev Str., 1113 Sofia, Bulgaria.

A series of squaric acid amides (synthesized in 66-99% isolated yields) and a set of chiral aminoalcohols were comparatively studied as ligands in a model reaction of reduction of α-chloroacetophenone with BH•SMe. In all cases, the aminoalcohols demonstrated better efficiency (up to 94% ), while only poor asymmetric induction was achieved with the corresponding squaramides. A mechanistic insight on the in situ formation and stability at room temperature of intermediates generated from ligands and borane as possible precursors of the oxazaborolidine-based catalytic system has been obtained by H DOSY and multinuclear 1D and 2D (H, B, C, N) NMR spectroscopy of equimolar mixtures of borane and selected ligands. Read More

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November 2021

Enantioselective recognition of chiral acids by supramolecular interactions with chiral AIEgens.

Chem Commun (Camb) 2021 Nov 23. Epub 2021 Nov 23.

Shenzhen Institute of Aggregate Science and Technology, School of Science and Engineering, The Chinese University of Hong Kong, Shenzhen, Guangdong 518172, China.

Novel chiral AIEgens bearing optically pure amino groups were synthesized and showed excellent discrimination for a series of chiral acidic compounds and amino acids. Interestingly, after supramolecular assembly with 4-sulfocalix[4]arene, the obtained complexes showed enhanced enantioselectivity for chiral acids. Read More

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November 2021

Enhancing cofactor regeneration of cyanobacteria for the light-powered synthesis of chiral alcohols.

Bioorg Chem 2022 Jan 10;118:105477. Epub 2021 Nov 10.

State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, PR China; Department of Bioengineering, East China University of Science and Technology, Shanghai 200237, PR China. Electronic address:

Cyanobacteria Synechocystis sp. PCC 6803 was exploited as green cell factory for light-powered asymmetric synthesis of aromatic chiral alcohols. The effect of temperature, light, substrate and cell concentration on substrate conversions were investigated. Read More

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January 2022

Characterizing the Diastereoisomeric Distribution of Phosphorothioate Oligonucleotides by Metal Ion Complexation Chromatography, In-Series Reversed Phase-Strong Anion Exchange Chromatography, and P NMR.

Anal Chem 2021 Nov 23. Epub 2021 Nov 23.

Ionis Pharmaceuticals, 2855 Gazelle Ct., Carlsbad, California 92010, United States.

Replacement of a non-bridging oxygen atom of the phosphate diester linkage of an oligonucleotide by sulfur conveys pharmacokinetic benefits, such as increased nuclease resistance and enhanced protein binding. Substitution renders the internucleotide linkages chiral, and so phosphorothioate diester (PS) oligonucleotides comprise complex mixtures of diastereoisomers. Currently, chromatographic separation of individual diastereoisomers is limited to oligonucleotides that contain no more than about four or five PS linkages. Read More

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November 2021

Amino acid-derived bisphenolate palladium complexes as C-C coupling catalysts.

Dalton Trans 2021 Nov 22. Epub 2021 Nov 22.

Institute of Chemical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK.

A series of amine bisphenol (ABP) pro-ligands featuring amino acid ester pendant arms were prepared. Optimisation of the synthetic method allowed the facile incorporation of naturally occurring, chiral amino acids into the ABP scaffold with minimal racemisation. Reaction of the pro-ligands (LH) with Pd(OAc), in the presence of amines, led to the formation of complexes with an unprecedented pincer-like O,N,O coordination mode around the Pd centre. Read More

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November 2021

Asymmetric construction of acyclic quaternary stereocenters via direct enantioselective additions of α-alkynyl ketones to allenamides.

Nat Commun 2021 Nov 18;12(1):6700. Epub 2021 Nov 18.

School of Physical Science and Technology, ShanghaiTech University, 201210, Shanghai, China.

Acyclic quaternary stereocenters are widely present in a series of biologically active natural products and pharmaceuticals. However, development of highly efficient asymmetric catalytic methods for the construction of these privileged motifs represents a longstanding challenge in organic synthesis. Herein, an efficient chiral phosphoric acid catalyzed direct asymmetric addition of α-alkynyl acyclic ketones with allenamides has been developed, furnishing the acyclic all-carbon quaternary stereocenters with excellent regioselectivities and high enantioselectivities. Read More

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November 2021

Cooperative Asymmetric Cation-Binding Catalysis.

Acc Chem Res 2021 Nov 16. Epub 2021 Nov 16.

Department of Chemistry, Sungkyunkwan University, Suwon, 440-746 Korea.

ConspectusAsymmetric cation-binding catalysis in principle enables the use of (alkali) metal salts, otherwise insoluble in organic solvents, as reagents and effectors in enantioselective reactions. However, this concept has been a formidable challenge due to the difficulties associated with creating a highly organized chiral environment for cations and anions simultaneously. Over the last four decades, various chiral crown ethers have been developed as cation-binding phase-transfer catalysts and examined in asymmetric catalysis. Read More

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November 2021

Biosynthesis of l-phosphinothricin with enzymes from chromosomal integrated expression in .

3 Biotech 2021 Nov 28;11(11):477. Epub 2021 Oct 28.

Key Laboratory of Bioorganic Synthesis of Zhejiang Province, College of Biotechnology and Bioengineering, Zhejiang University of Technology, Hangzhou, 310014 China.

Phosphinothricin (PPT) is one of the most prevalently using herbicides. The commercial phosphinothricin products are generally in the form of a racemic mixture, of which only the l-phosphinothricin (L-PPT) gives herbicidal function. Synthesis of optically pure L-PPT by deracemization of D/L-PPT is a promising way to cut down the environmental burden and manufacturing cost. Read More

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November 2021

Identification of (6S)-cyclopropyl-6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamines as new HBV capsid assembly modulators.

Eur J Med Chem 2021 Nov 6:113974. Epub 2021 Nov 6.

CAMS Key Laboratory of Antiviral Drug Research, Beijing Key Laboratory of Antimicrobial Agents, NHC Key Laboratory of Biotechnology of Antibiotics, Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, 100050, China. Electronic address:

GYH2-18 is a type II HBV CAM with 6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxamine (DPPC) skeleton discovered by Roche INC. A series of GYH2-18 derivatives were designed, synthesized and evaluated for their anti-HBV activity. Two compounds 2f and 3k exhibited excellent anti-HBV activity, low cytotoxicity and accepted oral PK profiles. Read More

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November 2021

Organocatalytic Asymmetric [2 + 4] Cycloadditions of 3-Vinylindoles with -Quinone Methides.

Molecules 2021 Nov 8;26(21). Epub 2021 Nov 8.

School of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou 221116, China.

Catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with -quinone methides and their precursors were carried out in the presence of chiral phosphoric acid to afford a series of indole-containing chroman derivatives with structural diversity in overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr) and moderate to excellent enantioselectivities (up to 98% ee). This approach not only enriches the chemistry of catalytic asymmetric cycloadditions involving 3-vinylindoles but is also useful for synthesizing chiral chroman derivatives. Read More

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November 2021

Discovery of a Series of Theophylline Derivatives Containing 1,2,3-Triazole for Treatment of Non-Small Cell Lung Cancer.

Front Pharmacol 2021 26;12:753676. Epub 2021 Oct 26.

The Eighth Affiliated Hospital, Sun Yat-sen University, Shenzhen, China.

Chemotherapy is the most common clinical treatment for non-small cell lung cancer (NSCLC), but low efficiency and high toxicity of current chemotherapy drugs limit their clinical application. Therefore, it is urgent to develop hypotoxic and efficient chemotherapy drugs. Theophylline, a natural compound, is safe and easy to get, and it can be used as a modified scaffold structure and hold huge potential for developing safe and efficient antitumor drugs. Read More

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October 2021

Synthesis, biological evaluation, and molecular docking studies of deoxygenated C-glycosides as LpxC inhibitors.

Bioorg Chem 2021 Dec 6;117:105403. Epub 2021 Oct 6.

Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany; German Center for Infection Research (DZIF), Partner Site Hamburg-Lübeck-Borstel-Riems, Germany. Electronic address:

The bacterial deacetylase LpxC is a promising target for the development of novel antibiotics being selectively active against Gram-negative bacteria. In chiral pool syntheses starting from d- and l-ribose, a series regio- and stereoisomeric monohydroxytetrahydrofuran derivatives was synthesized and tested for LpxC inhibitory and antibacterial activities. Molecular docking studies were performed to rationalize the obtained structure-activity relationships. Read More

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December 2021

Circularly polarized luminescence of Eu(III) complexes with chiral 1,1'-bi-2-naphtol-derived bisphosphate ligands.

Chirality 2021 Nov 8. Epub 2021 Nov 8.

CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226, Univ Rennes, Rennes, France.

The interest for lanthanide circularly polarized luminescence (CPL) has been quickly growing for 10 years. However, very few of these studies have involved correlation between the dissymmetry factor (g ) and the chemical modifications in a series of chiral ligands. Four polymeric compounds of Eu(III) were prepared by using a series of binaphtyl derivatives for which the size of the π system as well as the number of stereogenic elements (i. Read More

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November 2021

A novel isosteviol-based bifunctional squaramide organocatalyst for enantioselective Michael addition of acetylacetone to nitroolefins.

Chirality 2021 Nov 8. Epub 2021 Nov 8.

Faculty of Science, Henan University of Animal Husbandry and Economy, Zhengzhou, China.

Chiral amine-squaramide is a kind of effective hydrogen bond donor bifunctional catalyst to promote many asymmetric transformations. In this paper, novel chiral tertiary amine-squaramide derived from the natural product of the stevioside was developed and applied into the asymmetric Michael addition of acetylacetone to nitroolefins. This asymmetric reaction performed well, and a series of enantiomerically enriched compounds were obtained in high yields (up to 96%) with excellent enantioselectivities (up to 99% ee). Read More

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November 2021

Cobalt-Catalysed Asymmetric Addition and Alkylation of Secondary Phosphine Oxides for the Synthesis of P-Stereogenic Compounds.

Angew Chem Int Ed Engl 2021 Nov 5. Epub 2021 Nov 5.

School of Chemistry and Chemical Engineering, Shaanxi Normal University, 620 Xi Changan Street, Xi'an, 710119, China.

The catalytic asymmetric synthesis of P-chiral phosphorus compounds is an important way to construct P-chiral ligands. Herein, we report a new strategy that adopts the pyridinyl moiety as the coordinating group in the cobalt-catalysed asymmetric nucleophilic addition/alkylation of secondary phosphine oxides. A series of tertiary phosphine oxides were generated with up to 99 % yield and 99. Read More

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November 2021

Photoredox-Catalyzed Synthesis of Remote Fluoroalkylated Azaarene Derivatives and the α-Deuterated Analogues via 1,-Hydrogen-Atom-Transfer-Involving Radical Reactions.

Org Lett 2021 Nov 1;23(22):8744-8749. Epub 2021 Nov 1.

School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, P. R. China.

A modular strategy to access the remote fluoroalkylated azaarene derivatives and the α-deuterated analogues, which are the isosteres of many pharmaceutically important compounds, is reported. Transformations under the sustainable photoredox catalysis platform could efficiently experience cascade radical addition, 1,-hydrogen atom transfer (HAT), and single-electron reduction to offer the crucial anions α to azaarenes. Through reacting with HO or the inexpensive DO, two series of valuable products were obtained in high yields with substantial deuterium incorporation. Read More

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November 2021

Chelating Phosphine-N-Heterocyclic Carbene Platinum Complexes via Catalytic Asymmetric Hydrophosphination and Their Cytotoxicity Toward MKN74 and MCF7 Cancer Cell Lines.

Inorg Chem 2021 Nov 28;60(22):17276-17287. Epub 2021 Oct 28.

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.

A series of activated vinyl azoles was hydrophosphinated in the presence of a chiral palladacycle catalyst under mild conditions to give enantioenriched phosphine azoles with moderate enantioselectivities and yields. The racemic phosphine azoles were transformed into eleven novel chelating phosphine-N-heterocyclic carbene (NHC) platinum complexes. The drug efficacies of nine selected phosphine-NHC platinum(II) chlorides in two cancer cell lines (MKN74 and MCF7) were evaluated, and two were found to exhibit activities comparable to that of cisplatin. Read More

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November 2021

Organocatalytic Direct Asymmetric Indolization from Anilines by Enantioselective [3 + 2] Annulation.

Org Lett 2021 Nov 26;23(21):8434-8438. Epub 2021 Oct 26.

We report the efficient syntheses of chiral tetrahydroindole pyrazolinones by the asymmetric [3 + 2] cascade cyclizations (indolizations) of simple aniline derivatives with pyrazolinone ketimines as 2C synthons. The chiral phosphoric-acid-catalyzed system uses a concerted π-π interaction/dual H-bond control strategy to catalytically direct the asymmetric aniline, which undergoes a highly chemo-, regio-, and enantioselective [3 + 2] cascade annulation, furnishing a series of optically active tetra-hydroindole pyrazolinones with two contiguous chiral aza-quaternary carbon centers in excellent yields with excellent enantioselectivities. This method features a relatively broad substrate scope for amines and 2-naphthylamines and highlights the emerging value of direct chiral indolizations from simple amine sources in organic synthesis. Read More

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November 2021

Chiral analysis of pantolactone with molecular rotational resonance spectroscopy.

Chirality 2021 Oct 26. Epub 2021 Oct 26.

Department of Chemistry, University of Virginia, Charlottesville, Virginia, USA.

A molecular rotational resonance spectroscopy method for measuring the enantiomeric excess of pantolactone, an intermediate in the synthesis of panthenol and pantothenic acid, is presented. The enantiomers are distinguished via complexation with a small chiral tag molecule, which produces diastereomeric complexes in the pulsed jet expansion used to inject the sample into the spectrometer. These complexes have distinct moments of inertia, so their spectra are resolved by MRR spectroscopy. Read More

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October 2021

A Strategy for Selective Catalytic B-H Functionalization of -Carboranes.

Acc Chem Res 2021 11 24;54(21):4065-4079. Epub 2021 Oct 24.

Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

Carboranes are a class of polyhedral carbon-boron molecular clusters featuring three-dimensional aromaticity, which are often considered as 3D analogues of benzene. Their unique structural and electronic properties make them invaluable building blocks for applications ranging from functional materials to versatile ligands to pharmaceuticals. Thus, selective functionalization of carboranes has received tremendous research interest. Read More

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November 2021

Synthesis and Biological Application of Isosteviol-Based 1,3-Aminoalcohols.

Int J Mol Sci 2021 Oct 18;22(20). Epub 2021 Oct 18.

Interdisciplinary Excellence Center, Institute of Pharmaceutical Chemistry, University of Szeged, H-6720 Szeged, Hungary.

Starting from isosteviol, a series of diterpenoid 1,3-aminoalcohol derivatives were stereoselectively synthesised. The acid-catalysed hydrolysis and rearrangement of natural stevioside gave isosteviol, which was transformed to the key intermediate methyl ester. In the next step, Mannich condensation of diterpenoid ketone, paraformaldehyde, and secondary amines resulted in the formation of 1,3-aminoketones with different stereoselectivities. Read More

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October 2021

Box-copper catalyzed cascade asymmetric amidation for chiral -methylene aminoindoline derivatives.

Org Biomol Chem 2021 Nov 10;19(43):9373-9378. Epub 2021 Nov 10.

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, P. R. China.

Enantioselective copper-catalyzed cascade inter- and intramolecular amidation was achieved between ethynyl benzoxazinanones and α-halohydroxamates in the presence of an indapybox ligand. The one-pot cascade transformation was triggered by the attack of hydroxamates to dipolar copper-allenylidene intermediates, followed by a nucleophilic annulation reaction. Thus, a series of -methylene 3-aminoindoline derivatives were obtained in good yields with high enantioselectivities under mild reaction conditions. Read More

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November 2021

[B-Cl-B] Cations: Chloroborane Masked Chiral Borenium Ions.

Inorg Chem 2021 Nov 21;60(21):16266-16272. Epub 2021 Oct 21.

Department of Chemistry, National Taiwan University, Taipei 10617, Taiwan.

A tricoordinate borenium ion has received considerable attention in recent years for its applications in Lewis acid catalysis. Over the years, asymmetric catalysis mediated by a chiral borenium ion has also been developed. To stabilize the electron-deficient boron atom, a series of chloroborane masked borenium ions featuring the symmetrical [B-Cl-B] linkage are prepared and utilized as the catalyst for the enantioselective Diels-Alder cycloaddition of cyclopentadiene and 2,2,2-trifluoroethyl acrylate. Read More

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November 2021

Lanthanide Identity Governs Guest-Induced Dimerization in Ln [15-MC -5]) Metallacrowns.

Chemistry 2021 Oct 12. Epub 2021 Oct 12.

Dipartimento di Scienze Chimiche, Università degli Studi di Catania, Viale Andrea Doria 6, 95125, Catania, Italy.

Series of lanthanide-containing metallic coordination complexes are frequently presented as structurally analogous, due to the similar chemical and coordinative properties of the lanthanides. In the case of chiral (Ln [15-MC -5]) metallacrowns (MCs), which are well established supramolecular hosts, the formation of dimers templated by a dicarboxylate guest (muconate) in solution of neutral pH is herein shown to have a unique dependence on the identity of the MC's central lanthanide. Calorimetric data and nuclear magnetic resonance diffusion studies demonstrate that MCs containing larger or smaller lanthanides as the central metal only form monomeric host-guest complexes whereas analogues with intermediate lanthanides (for example, Eu, Gd, Dy) participate in formation of dimeric host-guest-host compartments. Read More

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October 2021

Direct reductive amination of ketones with ammonium salt catalysed by Cp*Ir(III) complexes bearing an amidato ligand.

Org Biomol Chem 2021 Oct 27;19(41):8934-8939. Epub 2021 Oct 27.

Shenzhen Institute of Advanced Technology, Chinese Academy of Sciences, Shenzhen 518055, Guangdong, China.

A series of half-sandwich Ir(III) complexes 1-6 bearing an amidato bidentate ligand were conveniently synthesized and applied to the catalytic Leuckart-Wallach reaction to produce racemic α-chiral primary amines. With 0.1 mol% of complex 1, a broad range of ketones, including aryl ketones, dialkyl ketones, cyclic ketones, α-keto acids, α-keto esters and diketones, could be transformed to their corresponding primary amines with moderate to excellent yields (40%-95%). Read More

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October 2021

Cobalt-Catalyzed Asymmetric 1,4-Hydroboration of Enones with HBpin.

Authors:
Xiang Ren Zhan Lu

Org Lett 2021 Nov 12;23(21):8370-8374. Epub 2021 Oct 12.

Department of Chemistry, Zhejiang University, Hangzhou 310058, China.

Herein, a series of new 8-OIQ cobalt complexes were synthesized and used for cobalt-catalyzed chemo- and enantioselective 1,4-hydroboration of enones with HBpin to access chiral -disubstituted ketones with good to excellent chemo- and enantioselectivties. This protocol is operationally simple and shows a broad substrate scope. Read More

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November 2021

Anion-Dependent Outstanding Luminescence Enhancement of Eu(D-facam) Upon Coexistence With the Tetramethylammonium Cation.

Chemphyschem 2021 Oct 7. Epub 2021 Oct 7.

Graduate School of Engineering, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba, 263-8522, Japan.

The effect of a series of tetramethylammonium salts with different counter anions on the photophysical properties of a chiral Eu(III) complex (Eu(D-facam) ) was investigated. Anion-dependent luminescence of the Eu(III) complex was observed, and particularly in the presence of acetate ions, an outstanding luminescence enhancement (>300 times) and induced circularly polarized luminescence (g =-0.63) were obtained. Read More

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October 2021