Commenced in January 2007
Frequency: Monthly
Edition: International
Paper Count: 61

Search results for: chiral metamaterials

61 Comparative Investigation of Miniaturized Antennas Based on Chiral Slotted Ground Plane

Authors: Oussema Tabbabi, Mondher Laabidi, Fethi Choubani, J. David


This study presents a miniaturized antenna based on chiral metamaterials slotted ground plane. To decrease resonant frequency while keeping the antennas physical dimensions the same, we propose a two novel patch antennas with double Z and cross slots on the ground plane. The length of the each type of slot are also altered to investigate the effect on miniaturization performance. Resonance frequency reduction has been achieved nearly to 30% and 23% as well as size reduction of almost 28% and 22% for the double Z and the cross shape respectively.

Keywords: chiral metamaterials, miniaturized antenna, miniaturization, resonance frequency

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60 Synthesis and Characterization of Chiral Dopant Based on Schiff's Base Structure

Authors: Hong-Min Kim, Da-Som Han, Myong-Hoon Lee


CLCs (Cholesteric liquid crystals) draw tremendous interest due to their potential in various applications such as cholesteric color filters in LCD devices. CLC possesses helical molecular orientation which is induced by a chiral dopant molecules mixed with nematic liquid crystals. The efficiency of a chiral dopant is quantified by the HTP (helical twisting power). In this work, we designed and synthesized a series of new chiral dopants having a Schiff’s base imine structure with different alkyl chain lengths (butyl, hexyl and octyl) from chiral naphthyl amine by two-step reaction. The structures of new chiral dopants were confirmed by 1H-NMR and IR spectroscopy. The properties were investigated by DSC (differential scanning calorimetry calorimetry), POM (polarized optical microscopy) and UV-Vis spectrophotometer. These solid state chiral dopants showed excellent solubility in nematic LC (MLC-6845-000) higher than 17wt%. We prepared the CLC(Cholesteric Liquid Crystal) cell by mixing nematic LC (MLC-6845-000) with different concentrations of chiral dopants and injecting into the sandwich cell of 5μm cell gap with antiparallel alignment. The cholesteric liquid crystal phase was confirmed from POM, in which all the samples showed planar phase, a typical phase of the cholesteric liquid crystals. The HTP (helical twisting power) is one of the most important properties of CLC. We measured the HTP values from the UV-Vis transmittance spectra of CLC cells with varies chiral dopant concentration. The HTP values with different alkyl chains are as follows: butyl chiral dopant=29.8μm-1; hexyl chiral dopant= 31.8μm-1; octyl chiral dopant=27.7μm-1. We obtained the red, green and blue reflection color from CLC cells, which can be used as color filters in LCDs applications.

Keywords: cholesteric liquid crystal, color filter, display, HTP

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59 Characterization of 3D Printed Re-Entrant Chiral Auxetic Geometries

Authors: Tatheer Zahra


Auxetic materials have counteractive properties due to re-entrant geometry that enables them to possess Negative Poisson’s Ratio (NPR). These materials have better energy absorbing and shock resistance capabilities as compared to conventional positive Poisson’s ratio materials. The re-entrant geometry can be created through 3D printing for convenient application of these materials. This paper investigates the mechanical properties of 3D printed chiral auxetic geometries of various sizes. Small scale samples were printed using an ordinary 3D printer and were tested under compression and tension to ascertain their strength and deformation characteristics. A maximum NPR of -9 was obtained under compression and tension. The re-entrant chiral cell size has been shown to affect the mechanical properties of the re-entrant chiral auxetics.

Keywords: auxetic materials, 3D printing, Negative Poisson’s Ratio, re-entrant chiral auxetics

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58 Separation of Some Pyrethroid Insecticides by High-Performance Liquid Chromatography

Authors: Fairouz Tazerouti, Samira Ihadadene


Pyrethroids are synthetic pesticides that originated from the modification of natural pyrethrins to improve their biological activity and stability. They are a family of chiral pesticides with a large number of stereoisomers. Enantiomers of synthetic pyretroids present different insecticidal activity, toxicity against aquatic invertebrates and persistence in the environment so the development of rapid and sensitive chiral methods for the determination of different enantiomers is necessary. In this study, the separation of enantiomers of pyrethroid insecticides has been systematically studied using three commercially chiral high-performance liquid chromatography columns. Useful resolution was obtained for compounds with a variety of acid and alcohol moieties, and containing one to four chiral centres. The chromatographic behaviour of the diastereomers of some of these insecticides by using normal, polar and reversed mobile phase mode were also examined.

Keywords: pesticides, analysis, liquid chromatography, pyrethroids

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57 Asymmetric Synthesis of β- and γ-Borylated Amines via Rh-Catalyzed Hydroboration of Allylamine Derivatives

Authors: Rukshani Wickrama-Arachchi, Tanner Metz, James M. Takacs


Amines bearing γ-stereocenters are important structural motifs found in many biologically active compounds. Regioselective Rh-catalyzed asymmetric hydroboration of acyclic allylamines is used to synthesize amines bearing chiral β- and γ-boronic esters yields up to 70% with 98:2 enantioselectivity. The major enantiomeric outcome can be independent of starting alkene geometry, revealing that cis/trans-isomerization of alkene can occur before hydroboration. Stereospecific transformations of the newly generated C-B bond illustrates the utility of these chiral synthons.

Keywords: allylamines, borylated amines, chiral amines, hydroboration, rhodium-catalysis

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56 Separation of Fexofenadine Enantiomers Using Beta Cyclodextrin as Chiral Counter Ion in Mobile Phase

Authors: R. Fegas, S. Zerkout, S. Taberkokt, M. Righezza


The present work demonstrate the potential of Betacyclodextrine (BCD) for the chiral analysis of a drug .Various separation mechanisms were applied and several parameters affecting the separation were studied, including the type and concentration of chiral selector, and pH of buffer. A simple and sensitive high-performance liquid chromatography (HPLC) method was developed as an assay for fexofenadine enantiomers in pharmaceutical preparation. Fexofenadine enantiomers were separated using a mobile phase of 0.25mM NaH2PO4–acetonitrile (65:35, v/v) – Betacyclodextrine on achiral phenyl-urea column at a flow rate of 1ml/min and measurement at 220nm. The chiral mechanism of separation was mainly based on specific interaction between the solute and the stationary phase. The retention was directly controlled by mobile phase composition but not the selectivity which results of the two mechanisms, electrostatic interactions and partition mechanism.

Keywords: fexofenadine enantiomer, HPLC, achiral phenyl-urea column

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55 Functionalization of Polypropylene with Chiral Monomer for Improving Hemocompatibility

Authors: Xiaodong Xu, Dan Zhao, Xiujuan Chang, Chunming Li, Huiyun Zhou, Xin Li, Qiang Shi, Shifang Luan, Jinghua Yin


Polypropylene (PP) is one of the most commonly used plastics because of its low density, outstanding mechanical properties, and low cost. However, its drawbacks such as low surface energy, poor dyeability, lack of chemical functionalities, and poor compatibility with polar polymers and inorganic materials, have restricted the application of PP. To expand its application in biomedical materials, functionalization is considered to be the most effective way. In this study, PP was functionalized with a chiral monomer, (S)-1-acryloylpyrrolidine-2-carboxylic acid ((S)-APCA), by free-radical grafting in the solid phase. The grafting degree of PP-g-APCA was determined by chemical titration method, and the chemical structure of functionalized PP was characterized by FTIR spectroscopy, which confirmed that the chiral monomer (S)-APCA was successfully grafted onto PP. Static water contact angle results suggested that the surface hydrophilicity of PP was significantly improved by solid phase grafting and assistance of surface water treatment. Protein adsorption and platelet adhesion results showed that hemocompatibility of PP was greatly improved by grafting the chiral monomer.

Keywords: functionalization, polypropylene, chiral monomer, hemocompatibility

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54 Asymmetric Synthesis of Catalponol Using Chiral Iridium Catalyst

Authors: Takeyuki Suzuki, Ismiyarto, Da-Yang Zhou, Kaori Asano, Hiroaki Sasai


The development of catalytic asymmetric reaction is important for the synthesis of natural products. To construct the multiple stereogenic centers, the desymmetrization of meso compounds is powerful strategy for the synthesis of chiral molecules. Oxidative desymmetrization of meso diols using chiral iridium catalyst provides a chiral hydroxyl ketone. The reaction is practical and an environmentally benign method which does not require the use of stoichiometric amount of heavy metals. This time we report here catalytic asymmetric synthesis of catalponol based on tandem coupling of meso-diols and an aldehyde. The tandem reaction includes oxidative desymmetrization of meso-diols, aldol condensation with an aldehyde. The reaction of meso-diol, benzaldehyde in the presence of a catalytic amount of chiral Ir complex and CsOH in tetrahydrofuran afforded the desired benzylidene ketone in 82% yield with 96% ee (enantiomeric excess). Next, we applied this benzylidene ketone derivative to the synthesis of catalponol. The corresponding benzylidene ketone was obtained in 87% yield with 99% ee. Finally, catalponol was synthesized by the regio- and stereo-selective reduction of dienone moiety in good yield.

Keywords: catalponol, desymmetrization, iridium, oxidation

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53 Chiral Carbon Quantum Dots for Paper-Based Photoluminescent Sensing Platforms

Authors: Erhan Zor, Funda Copur, Asli I. Dogan, Haluk Bingol


Current trends in the wide-scale sensing technologies rely on the development of miniaturized, rapid and easy-to-use sensing platforms. Quantum dots (QDs) with strong and easily tunable luminescence and high emission quantum yields have become a well-established photoluminescent nanomaterials for sensor applications. Although the majority of the reports focused on the cadmium-based QDs which have toxic effect on biological systems and eventually would cause serious environmental problems, carbon-based quantum dots (CQDs) that do not contain any toxic class elements have attracted substantial research interest in recent years. CQDs are small carbon nanostructures (less than 10 nm in size) with various unique properties and are widely-used in different fields during the last few years. In this respect, chiral nanostructures have become a promising class of materials in various areas such as pharmacology, catalysis, bioanalysis and (bio)sensor technology due to the vital importance of chirality in living systems. We herein report the synthesis of chiral CQDs with D- or L-tartaric acid as precursor materials. The optimum experimental conditions were examined and the purification procedure was performed using ethanol/water by column chromatography. The purified chiral CQDs were characterized by UV-Vis, FT-IR, XPS, PL and TEM techniques. The resultants display different photoluminescent characteristics due to the size and conformational difference. Considering the results, it can be concluded that chiral CQDs is expected to be used as optical chiral sensor in different platforms.

Keywords: carbon quantum dots, chirality, sensor, tartaric acid

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52 Inverted Umbrella-type Chiral Non-coplanar Ferrimagnetic Structure in Co(NO₃)₂

Authors: O. Maximova, I. L. Danilovich, E. B. Deeva, K. Y. Bukhteev, A. A. Vorobyova, I. V. Morozov, O. S. Volkova, E. A. Zvereva, I. V. Solovyev, S. A. Nikolaev, D. Phuyal, M. Abdel-Hafiez, Y. C. Wang, J. Y. Lin, J. M. Chen, D. I. Gorbunov, K. Puzniak, B. Lake, A. N. Vasiliev


The low-dimensional magnetic systems tend to reveal exotic spin liquid ground states or form peculiar types of long-range order. Among systems of vivid interest are those characterized by the triangular motif in two dimensions. The realization of either ordered or disordered ground state in a triangular, honeycomb, or kagome lattices is are dictated by the competition of exchange interactions, also being sensitive to anisotropy and the spin value of magnetic ions. While the low-spin Heisenberg systems may arrive at a spin liquid long-range entangled quantum state with emergent gauge structures, the high-spin Ising systems may establish the rigid non-collinear structures. This study presents the case of chiral non-coplanar inverted umbrella-type ferrimagnet formed in cobalt nitrate Co(NO₃)₂ below T

Keywords: chiral magnetic structures, low dimensional magnetic systems, umbrella-type ferrimagnets, chiral non-coplanar magnetic structures

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51 High-Performance Liquid Chromatographic Method with Diode Array Detection (HPLC-DAD) Analysis of Naproxen and Omeprazole Active Isomers

Authors: Marwa Ragab, Eman El-Kimary


Chiral separation and analysis of omeprazole and naproxen enantiomers in tablets were achieved using high-performance liquid chromatographic method with diode array detection (HPLC-DAD). Kromasil Cellucoat chiral column was used as a stationary phase for separation and the eluting solvent consisted of hexane, isopropanol and trifluoroacetic acid in a ratio of: 90, 9.9 and 0.1, respectively. The chromatographic system was suitable for the enantiomeric separation and analysis of active isomers of the drugs. Resolution values of 2.17 and 3.84 were obtained after optimization of the chromatographic conditions for omeprazole and naproxen isomers, respectively. The determination of S-isomers of each drug in their dosage form was fully validated.

Keywords: chiral analysis, esomeprazole, S-Naproxen, HPLC-DAD

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50 Additive Manufacturing of Titanium Metamaterials for Tissue Engineering

Authors: Tuba Kizilirmak


Distinct properties of porous metamaterials have been largely processed for biomedicine requiring a three-dimensional (3D) porous structure engaged with fine mechanical features, biodegradation ability, and biocompatibility. Applications of metamaterials are (i) porous orthopedic and dental implants; (ii) in vitro cell culture of metamaterials and bone regeneration of metamaterials in vivo; (iii) macro-, micro, and nano-level porous metamaterials for sensors, diagnosis, and drug delivery. There are some specific properties to design metamaterials for tissue engineering. These are surface to volume ratio, pore size, and interconnection degrees are selected to control cell behavior and bone ingrowth. In this study, additive manufacturing technique selective laser melting will be used to print the scaffolds. Selective Laser Melting prints the 3D components according to designed 3D CAD models and manufactured materials, adding layers progressively by layer. This study aims to design metamaterials with Ti6Al4V material, which gives benefit in respect of mechanical and biological properties. Ti6Al4V scaffolds will support cell attachment by conferring a suitable area for cell adhesion. This study will control the osteoblast cell attachment on Ti6Al4V scaffolds after the determination of optimum stiffness and other mechanical properties which are close to mechanical properties of bone. Before we produce the samples, we will use a modeling technique to simulate the mechanical behavior of samples. These samples include different lattice models with varying amounts of porosity and density.

Keywords: additive manufacturing, titanium lattices, metamaterials, porous metals

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49 Estimation of Enantioresolution of Multiple Stereogenic Drugs Using Mobilized and/or Immobilized Polysaccharide-Based HPLC Chiral Stationary Phases

Authors: Mohamed Hefnawy, Abdulrahman Al-Majed, Aymen Al-Suwailem


Enantioseparation of drugs with multiple stereogenic centers is challenging. This study objectives to evaluate the efficiency of different mobilized and/or immobilized polysaccharide-based chiral stationary phases to separate enantiomers of some drugs containing multiple stereogenic centers namely indenolol, nadolol, labetalol. The critical mobile phase variables (composition of organic solvents, acid/base ratios) were carefully studied to compare the retention time and elution order of all isomers. Different chromatographic parameters such as capacity factor (k), selectivity (α) and resolution (Rs) were calculated. Experimental conditions and the possible chiral recognition mechanisms have been discussed.

Keywords: HPLC, polysaccharide columns, enantio-resolution, indenolol, nadolol, labetalol

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48 Use of Metamaterials Structures to Reduce the SAR in the Human Head

Authors: Hafawa Messaoudi, Taoufik Aguili


Due to the rapid growth in the use of wireless communication systems, there has been a recent increase in public concern regarding the exposure of humans to Radio Frequency (RF) electromagnetic radiation. This is particularly evident in the case of mobile telephone handsets. Previously, the insertion of a ferrite sheet between the antenna and the human head, the use of conductive materials (such as aluminum), the use of metamaterials (SRR), frequency selective surface (FSS), and electromagnetic band gap (EBG) structures to design high performance devices were proposed as methods of reducing the SAR value. This paper aims to provide an investigation of the effectiveness of various available Specific Absorption Rate (SAR) reduction solutions.

Keywords: EBG, HIS, metamaterials, SAR reduction

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47 Selective Circular Dichroism Sensor Based on the Generation of Quantum Dots for Cadmium Ion Detection

Authors: Pradthana Sianglam, Wittaya Ngeontae


A new approach for the fabrication of cadmium ion (Cd2+) sensor is demonstrated. The detection principle is based on the in-situ generation of cadmium sulfide quantum dots (CdS QDs) in the presence of chiral thiol containing compound and detection by the circular dichroism spectroscopy (CD). Basically, the generation of CdS QDs can be done in the presence of Cd2+, sulfide ion and suitable capping compounds. In addition, the strong CD signal can be recorded if the generated QDs possess chiral property (from chiral capping molecule). Thus, the degree of CD signal change depends on the number of the generated CdS QDs which can be related to the concentration of Cd2+ (excess of other components). In this work, we use the mixture of cysteamine (Cys) and L-Penicillamine (LPA) as the capping molecules. The strong CD signal can be observed when the solution contains sodium sulfide, Cys, LPA, and Cd2+. Moreover, the CD signal is linearly related to the concentration of Cd2+. This approach shows excellence selectivity towards the detection of Cd2+ when comparing to other cation. The proposed CD sensor provides low limit detection limits around 70 µM and can be used with real water samples with satisfactory results.

Keywords: circular dichroism sensor, quantum dots, enaniomer, in-situ generation, chemical sensor, heavy metal ion

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46 Synthesis, Biological Evaluation and Molecular Modeling Studies on Chiral Chloroquine Analogues as Antimalarial Agents

Authors: Srinivasarao Kondaparla, Utsab Debnath, Awakash Soni, Vasantha Rao Dola, Manish Sinha, Kumkum Kumkum Srivastava, Sunil K. Puri, Seturam B. Katti


In a focused exploration, we have designed synthesized and biologically evaluated chiral conjugated new chloroquine (CQ) analogs with substituted piperazines as antimalarial agents. In vitro as well as in vivo studies revealed that compound 7c showed potent activity [for in vitro IC₅₀= 56.98nM (3D7), 97.76nM (K1); for in vivo (up to at the dose of 12.5 mg/kg); SI = 3510] as a new lead of antimalarial agent. Other compounds 6b, 6d, 7d, 7h, 8c, 8d, 9a, and 9c are also showing moderate activity against CQ-sensitive (3D7) strain and superior activity against resistant (K1) strain of P. falciparum. Furthermore, we have carried out docking and 3D-QSAR studies of all in-house data sets (168 molecules) of chiral CQ analogs to explain the structure activity relationships (SAR). Our new findings specified the significance of H-bond interaction with the side chain of heme for biological activity. In addition, the 3D-QSAR study against 3D7 strain indicated the favorable and unfavorable sites of CQ analogs for incorporating steric, hydrophobic and electropositive groups to improve the antimalarial activity.

Keywords: piperazines, CQ-sensitive strain-3D7, in-vitro and in-vivo assay, docking, 3D-QSAR

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45 Modulating Plasmon Induced Transparency in Terahertz Metamaterials

Authors: Gagan Kumar, Koijam M. Devi, Amarendra K. Sarma, Dibakar Roy Chowdhury


Research in metamaterials has been gaining momentum over the past decade owing to its ability in controlling electromagnetic wave properties through careful design at the sub-wavelength scale. The metamaterials have led to several important phenomena which are useful in a variety of applications. One such phenomenon is the electromagnetically induced transparency (EIT) effect in which a narrow transparency region is created in an otherwise absorptive spectrum. In our work, we explore plasmon induced transparency (PIT) in terahertz metamaterials which is analogues to EIT effect. The PIT effect is achieved using the plasmonic metamaterials in which a unit cell is comprised of two C (2C) shaped resonators and a cut-wire (CW). When terahertz wave of a particular polarization is normally incident on the proposed metamaterials geometry, it strongly couples with the cut wire, resulting in the excitation of the bright mode. However due to the specific polarization of the incident beam, the fundamental modes of the C-shaped resonators are not excited by the incident terahertz, hence they are termed as the dark mode. The PIT effect occurs as a result of interference between the bright and the dark mode. In order to observe PIT effect, both the bright and dark modes should have similar resonant frequencies with a little deviation. We further have examined that the PIT window can be modulated by displacing the C-shaped resonators w.r.t. the cut-wire. The numerical observations for different coupling configurations can be explained through an equivalent lumped element circuit model. Moving ahead the PIT effect is further explored in a metamaterial comprising of a cross like structure and four C-shaped resonators. For such configuration, equally strong PIT effect is observed for two orthogonally polarized lights. Therefore, such metamaterials demonstrate a polarization independent PIT response w.r.t the incident terahertz radiation. The proposed study could be significant in the development of slow light devices and polarization independent sensing applications.

Keywords: terahertz, metamaterial, split ring resonator, plasmon

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44 Chiral Diphosphine Ligands and Their Transition Metal Diphosphine Complexes in Asymmetric Catalysis

Authors: Shannen Lorraine, Paul Maragh, Tara Dasgupta, Kamaluddin Abdur-Rashid


(R)-(4,4',6,6'-tetramethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine) (R-Ph-Garphos), and (S)-(4,4',6,6'-tetramethoxybiphenyl-2,2'-diyl)bis(diphenylphosphine) (S-Ph-Garphos) are novel, nucleophilic, chiral atropisomeric ligands. The research explored the synthesis of chiral transition metal complexes containing these ligands and their applications in various asymmetric catalytic transformations. Herein, the transition metal complexes having ruthenium(II), rhodium(I) and iridium(I) metal centres will be discussed. These are air stable complexes and were characterized by CHN analysis, 1H, 13C, and 31P NMR spectroscopy, and polarimetry. Currently, there is an emphasis on 'greener' catalysts and the need for 'green' solvents in asymmetric catalysis. As such, the Ph-Garphos ligands were demethylated thereby introducing hydroxyl moieties unto the ligand scaffold. The facile tunability of the biaryl diphosphines led to the preparation of the (R)-(4,4',6,6'-tetrahydroxybiphenyl-2,2'-diyl)bis(diphenylphosphine) (R-Ph-Garphos-OH), and (S)-(4,4',6,6'-tetrahydroxybiphenyl-2,2'-diyl)bis(diphenylphosphine) (S-Ph-Garphos-OH) ligands. These were successfully characterized by CHN analysis, 1H, 13C, and 31P NMR spectroscopy, and polarimetry. The use of the Ph-Garphos and Ph-Garphos-OH ligands and their transition metal complexes in asymmetric hydrogenations will be reported. Additionally, the scope of the research will highlight the applicability of the Ph-Garphos-OH ligand and its transitional metal complexes as 'green' catalysts.

Keywords: catalysis, asymmetric hydrogenation, diphosphine transition metal complexes, Ph-Garphos ligands

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43 Transformation of Glycals to Chiral Fused Aromatic Cores via Annulative π-Extension Reaction with Arynes

Authors: Nazar Hussain, Debaraj Mukherjee


Carbohydrate-derived chiral intermediates which contain arrays of defined stereocenters have found enormous applications in organic synthesis due to their inherent functional group, stereochemical and structural diversities as well as their ready availability. Stereodiversity of these classes of molecules has motivated synthetic organic chemistry over the years. One major challenge is control of relative configuration during construction of acyclic fragments. Here, we show that The Diels Alder addition of arynes to appropriately substituted vinyl/aryl glycals followed by π-extension via pyran ring opening smoothly furnished meta-disubstituted fused aromatic cores containing a stereo-defined orthogonally protected chiral side chain. The method is broad in terms of aryl homologation affording benzene, naphthalene, and phenanthrene derivatives. Base-induced deprotonation followed by cleavage of the allylic C-O bond appears to be the crucial steps leading to the development of aromaticity, which is the driving force behind the annulative π-extension process. The present protocol can be used for the synthesis of meta-disubstituted naphthalene aldehydes and substrates for aldolases.

Keywords: vinyl/C-2 aryl glycal, arynes, cyclization, ring opening

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42 Modeling and Simulation of Practical Metamaterial Structures

Authors: Ridha Salhi, Mondher Labidi, Fethi Choubani


Metamaterials have attracted much attention in recent years because of their electromagnetic exquisite proprieties. We will present, in this paper, the modeling of three metamaterial structures by equivalent circuit model. We begin by modeling the SRR (Split Ring Resonator), then we model the HIS (High Impedance Surfaces), and finally, we present the model of the CPW (Coplanar Wave Guide). In order to validate models, we compare the results obtained by an equivalent circuit models with numerical simulation.

Keywords: metamaterials, SRR, HIS, CPW, IDC

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41 Synthesis of (S)-Naproxen Based Amide Bond Forming Chiral Reagent and Application for Liquid Chromatographic Resolution of (RS)-Salbutamol

Authors: Poonam Malik, Ravi Bhushan


This work describes a very efficient approach for synthesis of activated ester of (S)-naproxen which was characterized by UV, IR, ¹HNMR, elemental analysis and polarimetric studies. It was used as a C-N bond forming chiral derivatizing reagent for further synthesis of diastereomeric amides of (RS)-salbutamol (a β₂ agonist that belongs to the group β-adrenolytic and is marketed as racamate) under microwave irradiation. The diastereomeric pair was separated by achiral phase HPLC, using mobile phase in gradient mode containing methanol and aqueous triethylaminephosphate (TEAP); separation conditions were optimized with respect to pH, flow rate, and buffer concentration and the method of separation was validated as per International Council for Harmonisation (ICH) guidelines. The reagent proved to be very effective for on-line sensitive detection of the diastereomers with very low limit of detection (LOD) values of 0.69 and 0.57 ng mL⁻¹ for diastereomeric derivatives of (S)- and (R)-salbutamol, respectively. The retention times were greatly reduced (2.7 min) with less consumption of organic solvents and large (α) as compared to literature reports. Besides, the diastereomeric derivatives were separated and isolated by preparative HPLC; these were characterized and were used as standard reference samples for recording ¹HNMR and IR spectra for determining absolute configuration and elution order; it ensured the success of diastereomeric synthesis and established the reliability of enantioseparation and eliminated the requirement of pure enantiomer of the analyte which is generally not available. The newly developed reagent can suitably be applied to several other amino group containing compounds either from organic syntheses or pharmaceutical industries because the presence of (S)-Npx as a strong chromophore would allow sensitive detection.This work is significant not only in the area of enantioseparation and determination of absolute configuration of diastereomeric derivatives but also in the area of developing new chiral derivatizing reagents (CDRs).

Keywords: chiral derivatizing reagent, naproxen, salbutamol, synthesis

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40 Chiral Amine Synthesis and Recovery by Using High Molecular Weight Amine Donors

Authors: Claudia Matassa, Matthias Hohne, Dominic Ormerod, Yamini Satyawali


Chiral amines integrate the backbone of several active pharmaceutical ingredients (APIs) used in modern medicine for the treatment of a vast range of diseases. Despite the demand, their synthesis remains challenging. Besides a range of chemicals and enzymatical methods, chiral amine synthesis using transaminases (EC 2.6.1.W) represents a useful alternative to access this important class of compounds. Even though transaminases exhibit excellent stereo and regioselectivity and the potential for high yield, the reaction suffers from a number of challenges, including the thermodynamic equilibrium, product inhibition, and low substrate solubility. In this work, we demonstrate a membrane assisted strategy for addressing these challenges. It involves the use of high molecular weight (HMW) amine donors for the transaminase-catalyzed synthesis of 4-phenyl-2-butylamine in both aqueous and organic solvent media. In contrast to common amine donors such as alanine or isopropylamine, these large molecules, provided in excess for thermodynamic equilibrium shifting, are easily retained by commercial nanofiltration membranes; thus a selective permeation of the desired smaller product amine is possible. The enzymatic transamination in aqueous media, combined with selective product removal shifted the equilibrium enhancing substrate conversion by an additional 25% compared to the control reaction. Along with very efficient amine product removal, there was undesirable loss of ketone substrate and low product concentration was achieved. The system was therefore further improved by performing the reaction in organic solvent (n-heptane). Coupling the reaction system with membrane-assisted product removal resulted in a highly concentrated and relatively pure ( > 97%) product solution. Moreover, a product yield of 60% was reached, compared to 15% without product removal.

Keywords: amine donor, chiral amines, in situ product removal, transamination

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39 Method Development and Validation for Quantification of Active Content and Impurities of Clodinafop Propargyl and Its Enantiomeric Separation by High-Performance Liquid Chromatography

Authors: Kamlesh Vishwakarma, Bipul Behari Saha, Sunilkumar Sing, Abhishek Mishra, Sreenivas Rao


A rapid, sensitive and inexpensive method has been developed for complete analysis of Clodinafop Propargyl. Clodinafop Propargyl enantiomers were separated on chiral column, Chiral Pak AS-H (250 mm. 4.6mm x 5µm) with mobile phase n-hexane: IPA (96:4) at flow rate 1.5 ml/min. The effluent was monitored by UV detector at 230 nm. Clodinafop Propagyl content and impurity quantification was done with reverse phase HPLC. The present study describes a HPLC method using simple mobile phase for the quantification of Clodinafop Propargyl and its impurities. The method was validated and found to be accurate, precise, convenient and effective. Moreover, the lower solvent consumption along with short analytical run time led to a cost effective analytical method.

Keywords: Clodinafop Propargyl, method, validation, HPLC-UV

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38 Crystallization Based Resolution of Enantiomeric and Diastereomeric Derivatives of myo-Inositol

Authors: Nivedita T. Patil, M. T. Patil, M. S. Shashidhar, R. G. Gonnade


Cyclitols are cycloalkane polyols which have raise attention since they have numerous biological and pharmaceutical properties. Among these, inositols are important cyclitols, which constitute a group of naturally occurring polyhydric alcohols. Myo, scyllo, allo, neo, D-chiro- are naturally occurring structural isomer of inositol while other four isomers (L-chiro, allo, epi-, and cis-inositol) are derived from myo-inositol by chemical synthesis. Myo-inositol, most abundant isomer, plays an important role in signal transduction process and for the treatment of type 2 diabetes, bacterial infections, stimulation of menstruation, ovulation in polycystic ovary syndrome, improvement of osteogenesis, and in treatment of neurological disorders. Considering the vast application of the derivatives, it becomes important to supply these compounds for further studies in quantitative amounts, but the synthesis of suitably protected chiral inositol derivatives is the key intermediates in most of the synthesis which is difficult. Chiral inositol derivatives could also be of interest to synthetic organic chemists as they could serve as potential starting materials for the synthesis of several natural products and their analogs. Thus, obtaining chiral myo-inositol derivatives in a more eco-friendly way is need for current inositol chemistry. Thus, the resolution of nonracemates by preferential crystallization of enantiomers has not been reported as a method for inositol derivatives. We are optimistic that this work might lead to the development of the two tosylate enantiomers as synthetic chiral pool molecules for organic synthesis. Resolution of racemic 4-O-benzyl 6-O-tosyl myo-inositol 1, 3, 5 orthoformate was successfully achieved on multigram scale by preferential crystallization, which is more scalable, eco-friendly method of separation than other reported methods. The separation of the conglomeric mixture of tosylate was achieved by suspending the mixture in ethyl acetate till the level of saturation is obtained. To this saturated clear solution was added seed crystal of the desired enantiomers. The filtration of the precipitated seed was carried out at its filtration window to get enantiomerically enriched tosylate, and the process was repeated alternatively. These enantiomerically enriched samples were recrystallized to get tosylate as pure enantiomers. The configuration of the resolved enantiomers was determined by converting it to previously reported dibenzyl ether myo-inositol, which is an important precursor for mono- and tetraphosphates. We have also developed a convenient and practical method for the preparation of enantiomeric 4-O and 6-O-allyl myo-inositol orthoesters by resolution of diastereomeric allyl dicamphante orthoesters on multigram scale. These allyl ethers can be converted to other chiral protected myo-inositol derivatives using routine synthetic transformations. The chiral allyl ethers can be obtained in gram quantities, and the methods are amenable to further scale-up due to the simple procedures involved. We believe that the work described enhances the pace of research to understand the intricacies of the myo-inositol cycle as the methods described provide efficient access to enantiomeric phosphoinositols, cyclitols, and their derivatives from the abundantly available myo-inositol as a starting material.

Keywords: cyclitols, diastereomers, enantiomers, myo-inositol, preferential crystallization, signal transduction

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37 Nelder-Mead Parametric Optimization of Elastic Metamaterials with Artificial Neural Network Surrogate Model

Authors: Jiaqi Dong, Qing-Hua Qin, Yi Xiao


Some of the most fundamental challenges of elastic metamaterials (EMMs) optimization can be attributed to the high consumption of computational power resulted from finite element analysis (FEA) simulations that render the optimization process inefficient. Furthermore, due to the inherent mesh dependence of FEA, minuscule geometry features, which often emerge during the later stages of optimization, induce very fine elements, resulting in enormously high time consumption, particularly when repetitive solutions are needed for computing the objective function. In this study, a surrogate modelling algorithm is developed to reduce computational time in structural optimization of EMMs. The surrogate model is constructed based on a multilayer feedforward artificial neural network (ANN) architecture, trained with prepopulated eigenfrequency data prepopulated from FEA simulation and optimized through regime selection with genetic algorithm (GA) to improve its accuracy in predicting the location and width of the primary elastic band gap. With the optimized ANN surrogate at the core, a Nelder-Mead (NM) algorithm is established and its performance inspected in comparison to the FEA solution. The ANNNM model shows remarkable accuracy in predicting the band gap width and a reduction of time consumption by 47%.

Keywords: artificial neural network, machine learning, mechanical metamaterials, Nelder-Mead optimization

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36 Fano-Resonance-Based Wideband Acoustic Metamaterials with Highly Efficient Ventilation

Authors: Xi-Wen Xiao, Tzy-Rong Lin, Chien-Hao Liu


Ventilated acoustic metamaterials have attracted considerable research attention due to their low-frequency absorptions and efficient fluid ventilations. In this research, a wideband acoustic metamaterial with auditory filtering ability and efficient ventilation capacity were proposed. In contrast to a conventional Fano-like resonator, a Fano-like resonator composed of a resonant unit and two nonresonant units with a large opening area of 68% for fluid passages was developed. In addition, the coupling mechanism to improve the narrow bandwidths of conventional Fano-resonance-based meta-materials was included. With a suitable design, the output sound waves of the resonant and nonresonant states were out of phase to achieve sound absorptions in the far fields. Therefore, three-element and five-element coupled Fano-like metamaterials were designed and simulated with the help of the finite element software to obtain the filtering fractional bandwidths of 42.5% and 61.8%, respectively. The proposed approach can be extended to multiple coupled resonators for obtaining ultra-wide bandwidths and can be implemented with 3D printing for practical applications. The research results are expected to be beneficial for sound filtering or noise reductions in duct applications and limited-volume spaces.

Keywords: fano resonance, noise reduction, resonant coupling, sound filtering, ventilated acoustic metamaterial

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35 Improvement and Miniaturization RFID Patch Antenna by Inclusion the Complementary Metamaterials

Authors: Seif Naoui, Lassaad Latrach, Ali Gharsallah


This paper is specialized to highlight the method of miniaturization and improvement the patch antenna by using the complementary metamaterial. This method is presented by a simple technique is composed a structure of patch antenna integrated in its surface a cell of complementary split ring resonator. This resonator is placed at the middle of the radiating patch in parallel with the transmission line and with a variable angle of orientation. The objective is to find the ultimate angle where the best results are obtained on improving the characteristics of the considered antenna. This motif widespread at the traceability applications by wireless communication for RFID technology at the operation frequency 2.45 GHz. Our contribution is based on studies empirical often presented in this article. All simulation results were made by the CST Microwave Studio.

Keywords: complimentary split ring resonators, computer simulation technology microwave studio, metamaterials patch antennas, microstrip patch antenna, radio frequency identification

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34 The Inversion of Helical Twist Sense in Liquid Crystal by Spectroscopy Methods

Authors: Anna Drzewicz, Marzena Tykarska


The chiral liquid crystal phases form the helicoidal structure, which is characterized by the helical pitch and the helical twist sense. In anticlinic smectic phase with antiferroelectric properties three types of helix temperature dependence have been obtained: increased helical pitch with temperature and right-handed helix, decreased helical pitch with temperature and left-handed helix and the inversion of both. The change of helical twist sense may be observed during the transition from one liquid crystal phase to another or within one phase for the same substance. According to Gray and McDonnell theory, the helical handedness depends on the absolute configuration of the assymetric carbon atom and its position related to the rigid core of the molecule. However, this theory does not explain the inversion of helical twist sense phenomenon. It is supposed, that it may be caused by the presence of different conformers with opposite handendess, which concentration may change with temperature. In this work, the inversion of helical twist sense in the chiral liquid crystals differing in the length of alkyl chain, in the substitution the benzene ring by fluorine atoms and in the type of helix handedness was tested by vibrational spectroscopy (infrared and raman spectroscopy) and by nuclear magnetic resonance spectroscopy. The results obtained from the vibrational spectroscopy confirm the presence of different conformers. Moreover, the analysis of nuclear magnetic resonance spectra is very useful to check, on which structural fragments the change of conformations are important for the change of helical twist sense.

Keywords: helical twist sense, liquid crystals, nuclear magnetic resonance spectroscopy, vibrational spectroscopy

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33 An Organocatalytic Construction of Vicinal Tetrasubstituted Stereocenters via Mannich Reaction of 2-Substituted Benzofuran-3-One with Isatin-Derived Ketimine

Authors: Koilpitchai Sivamuthuraman, Venkitasamy Kesavan


3-substituted 3-amino-2-oxindole skeleton bearing adjacent tetrasubstituted stereogenic centers is of great importance because of these heterocyclic motifs possess a wide range of pharmacological activity. The catalytic asymmetric construction of multi functionalised heterocyclic compound with adjacent tetrasubstituted stereocenters is one of the most difficult tasks in organic synthesis. To date, the most straightforward methodologies have been developed for synthesis of chiral 3-substituted 3-amino-2-oxindoles through the addition of carbon nucleophiles to isatin-derived ketimines. However, only a few successful examples have been described for the assembly of vicinal tetrasubstituted stereocenters using isatin derived ketimines as electrophiles. On the other hand, 2,2-Disubstituted benzofuran-3(2H)-ones and related frameworks are characteristic of a quaternary stereogenic center at C2 position present in quite a number of natural products and bioactive Molecules.Despite the intensive efforts devoted for the construction of 2,2-Disubstituted Benzofuran-3[2H]-one, there are only a few asymmetric methods such as organocatalytic Michael addition and enantioselective halogenations were reported till now. Due to the biological importance of oxindole and benzofuran-3-one, it is proposed here with the synthesis of hybrid molecule containing tetrasubstituted stereo centers through asymmetric organocatalysis. The addition of 2-substituted Benzofuran-3-one(1a) to isatin-derived ketimines(2a) using a bifunctional organocatalyst(catalyst IV or V), leading to chiral heterocyclic compounds containing both 3-amino 2-oxindole and benzofurn-3-one bearing vicinal quaternary stereocenters with good yields and excellent enantioselectivity. The present study extends the scope of the catalytic asymmetric Mannich reaction with isatin-derived ketimines, providing a new class of amino oxindole derivatives having benzofuran-3-one.

Keywords: asymmetric synthesis, benzofuran-3-one, isatin-derived ketimines, quaternary stereocenters

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32 In vitro and in vivo Potential Effect of the N-Acylsulfonamide Bis-oxazolidin-2-ones on Toxoplasma gondii

Authors: Benlaifa Meriem, Berredjem Hajira, Bouasla Radia, Berredjem Malika, Djebar Med Reda


Toxoplasmosis is a cosmopolitan infection due to Toxoplasma gondii (T.gondii). It is a significant cause of congenital disease and an important opportunistic pathogen which has become a worldwide increasing problem due to the AIDS epidemic. Current available drugs do not give satisfactory results and often have only a static and several adverse side effects as it is the case of pyrimethamine. So, the need to develop and evaluate new drugs is critical. The purpose of this study is to investigate the in vitro and in vivo effects of the new chiral N-acylsulfonamide bis-oxazolidin-2-ones on T.gondii. In this study, anti-T.gondii RH strain activities, of two new chiral N-acylsulfonamide bis-oxazolidin-2-ones were evaluated in vitro, using a MRC-5 fibroblast tissue cultures to determine the concentration that inhibit parasite multiplication by 50% (IC50) of each drug and in vivo, by PCR detection of the tachyzoites in mice ascites after new molecules treatment, using the 35-fold repetitive B1 gene of T.gondii. The in vitro results demonstrated that the treatment with the tested molecules decreased the amount of tachyzoites in cell culture in a dose-dependent manner. The inhibition was complete for concentrations over 4 mg/ml. The IC50 of Mol 1 and Mol 2 were 1.5 and 3 mg/ml, respectively, and were quite similar to the control one (2 mg/ml). The Mol 1 was highly active against T.gondii in cell cultures than Mol 2; these results were similar to those of sulfadiazine-treated group (p < 0.05). Toxoplasma-specific DNA was demonstrated in all ascites samples from infected mice of the different tested groups. Mol 1 showed better effect than Mol 2, but it did not completely inhibit the parasite proliferation. The intensity of amplification products increased when the treatment started late after infection. These findings suggest continuous parasite replication despite the treatment. In conclusion, our results showed a promising treatment effect of the tested molecules and suggest that in vitro, the Mol 1, and Mol 2 have a dose-dependent effect and a high cytotoxicity on the studied cells. The present study revealed that concentration and duration of tested molecules treatment are major factors that influence the course of Toxoplasma infection in infected mice.

Keywords: cytotoxicity, PCR, sulfonamide, Toxoplasma gondii

Procedia PDF Downloads 398