2023

Permanent URI for this collectionhttps://hdl.handle.net/1807/126404

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    Synthesis of a Fluorescent Chemical Probe for Imaging of L-Type Voltage Gated Calcium Channels
    (Canadian Science Publishing, 2023-11-28) Schroeder, Megan Danielle; Hellgren, Victor; Menard, Frederic
    Herein, we report the synthesis of a chemical probe for real-time visualization of L-type voltage-gated calcium channels (LTCCs) using fluorescence microscopy. The probe, FluoBar2, is based on a barbiturate ligand selective for LTCCs. FluoBar2 contains the organic fluorophore 5-carboxyfluorescein and was synthesized in seven total steps with a 22% overall yield.
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    Ionic Salt Cocrystals Studied via Multinuclear Solid-State Magnetic Resonance. A Case Study of Lithium 4-Methoxybenzoate:L-Proline Polymorphs
    (Canadian Science Publishing, 2023-11-23) Shi, Yishu; Bryce, David L.
    Lithium salts continue to find pharmaceutical applications, particularly as psychiatric medications. As with any active pharmaceutical ingredient, structural polymorphism is an important concern for lithium-based medications which can influence solubility and other physicochemical properties. Here we report a 13C, 1H, and 7Li magic-angle spinning solid-state nuclear magnetic resonance (MAS SSNMR) study of two 1:1 polymorphic ionic cocrystals of lithium 4-methoxybenzoate and L-proline (L4MPRO(α) and L4MPRO(β)). One-dimensional 13C cross-polarization magic-angle spinning and two-dimensional heteronuclear correlation NMR spectra hint at differential mobilities of the proline and benzoate moieties for the two polymorphs. Five key resonances differ in 13C chemical shift by more than 1 ppm between the two polymorphs, clearly distinguishing between them. Gauge-including projector-augmented-wave density functional theory (GIPAW DFT) calculations of 13C and 1H magnetic shielding constants correlate strongly with the experimental chemical shifts for both polymorphs. R2 and root-mean-square deviation metrics are shown to be insufficient in the case of 13C, but sufficient in the case of 1H, for differentiating between the polymorphs. 7Li satellite-transition MAS NMR of both polymorphs are identical, as are the computed lithium magnetic shielding constants, demonstrating the insensitivity of 7Li NMR to polymorphism in these samples. This work highlights the utility of solid-state NMR spectroscopy for examining ionic salt cocrystals and also highlights some caveats in this regard.
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    NMR characterization of novel interactions between p97 AAA+ ATPase and the p47 adapter revealing insights into substrate delivery mechanism
    (Canadian Science Publishing, 2023-11-14) Kim, Peter; Black, Megan; Perez, Felipe; Huang, Rui
    p97/VCP is an essential AAA+ ATPase involved in diverse cellular activities by interacting with an array of protein adapters that recruit p97 for specific tasks. p47 is one of the adapters that targets p97 for membrane remodeling by forming a stable complex with p97 through multivalent interactions. Here we report a pair of previously unidentified interactions between the N-terminal part of p47 (residue 1-94) and the N-terminal domain (NTD) of p97. Using NMR spectroscopy, we identify two binding sites on p47, one located on the UBA domain and the other on the intrinsically disordered linker, that interact with the same basic patch on p97 NTD, driven by electrostatic forces. Reciprocal NMR titration experiments between p47 (residue 1-94) and p97 NTD reveal that these interactions are relatively weak in nature with dissociation constants on the order of hundreds of micromolar to millimolar in trans. Structural models of the two interactions are developed based on NMR chemical shift perturbations, which reveal details of the tentative binding interfaces. Our findings provide new insights into the mechanism by which ubiquitinated substrates are delivered from p47 to p97 for unfolding.
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    Multiple Verdazyl Radicals Appended to a Triarylamine Scaffold
    (Canadian Science Publishing, 2023-09-30) Reiber, Sydney; Templeman-Vivian, Bennett; Mills, Michelle; Tremblay, Chris; Leitch, David; Chernick, Erin
    We report the synthesis of three triphenylamine-based verdazyl radicals. These include a mono, bis, and tris(verdazyl) at the 4-position(s) of the N–Ar groups, containing one, two, and three unpaired electrons, respectively. Each of these compounds is air stable, and fully characterized using EPR spectroscopy, high-resolution mass spectrometry, infrared spectroscopy, UV/Vis spectroscopy, and cyclic voltammetry. From the UV/Vis absorbance data, the optical absorbance energy gaps were found to be ~2.35 eV for all three verdazyl-containing compounds. Cyclic voltammetry was used to estimate the energy levels of the singly occupied molecular orbitals (SOMOs), which are -4.91 eV, -5.12 eV, and -4.98 eV for mono, bis, and tris(verdazyl) compounds respectively. Spin-spin exchange interactions were observed in the EPR spectra of both the bis and tris(verdazyl)s, leading to additional hyperfine coupling patterns and assignment of the ground states as triplet and quartet, respectively.
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    Synthesis and Antimalarial Activity of Novel 3-Substituted Chloroquine Derivatives
    (Canadian Science Publishing, 2023-07-22) Kapuku, Benita; Baakdah, Fadi; Georges, Elias; Bohle, D. Scott
    The synthesis and characterization of a series of new 3-substituted chloroquine (CQ) derivatives is reported along with their anti-malarial activity against CQ sensitive, 3D7, and CQ resistant, Dd2, strains of Plasmodium falciparum. The new CQ derivatives stem from the aroylation of 3-aminochloroquine which in turn is prepared in four efficient steps from 4,7-dichloroquinoline. Variation of the aroylation substituents and ring substitution patterns reveal that 4-substitution with electron-withdrawing moieties results in the lowest IC50 values, both in the same order of magnitude as CQ itself for the 3D7 strain. Given its activity against the resistant Dd2 strain, the 4-chlorobenzamido-CQ derivative is chosen as the lead compound for potential use in combination therapy.
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    Arrayed and Entangled Silicon Nanowires Using Au Nanoparticle Catalysts Prepared by Pulsed Laser-induced Dewetting
    (Canadian Science Publishing, 2023-06-23) Fulton, Alison Joy; Shi, Yujun
    The use of pulsed laser-induced dewetting (PLiD) is reported as a novel approach in the fabrication of Au nanoparticle (NP) catalytic arrays for the growth of Si nanowires (NWs) by chemical vapor deposition using SiCl4in the presence of H2. On polished Si substrates, PLiD generates Au NP catalysts with long-range order and narrow size distributions. It has been shown that the monodispersed distribution of Au NPs provides consistent diameter control of the as-grown Si NWs. A systematic exploration of the Si NW synthesis time, temperature and gas flow rates illustrates a level of tunability in terms of morphology, be it arrayed or entangled Si NWs, with varying experimental parameters. An investigation of the effect of growth temperature also showed that Si NWs can be synthesized at temperatures as low as 700 ⁰C when using SiCl4 as the precursor. The use of porous Si substrates enabled direct observation of the diameter-dependent growth due to the simultaneous presence of three Au NP size distributions. Growth from the small- and medium-size Au NP catalysts occurred first, followed by that from the large-size Au NPs, which was only observed at extended times or high SiCl4 flow rates. The delayed onset of growth from the large-size Au NPs is due to the longer time to achieve Si super-saturation of larger catalyst NPs. The morphology and diameter control of the as-grown Si NWs reported in this work makes this approach potentially useful towards applications such as nanoelectronics, sensors, and LIB electrodes depending on the desired morphology.
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    Synthesis of 2-arylpyridines by the Suzuki-Miyaura cross coupling of PyFluor with hetero(aryl) boronic acids and esters
    (Canadian Science Publishing, 2023-04-25) Rueda-Espinosa, Juan; Ramanayake, Dewni; Ball, Nicholas; Love, Jennifer
    The Suzuki-Miyaura cross-coupling of pyridine-2-sulfonyl fluoride (PyFluor) with hetero(aryl) boronic acids and pinacol boronic esters is reported. The reactions can be performed using Pd(dppf)Cl2 as the catalyst, at temperatures between 65 – 100 °C and in the presence of water and oxygen. This transformation generates 2-arylpyridines in modest to good yields (5-89%).
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    Development of carbon materials for sulfur cathodes in inorganic-based solid-state lithium sulfur batteries
    (Canadian Science Publishing, 2023-04-28) Yang, Zhao; Yu, Qihang; Thinphang-nga, Anna; Li, Xia
    Inorganic-based solid-state lithium-sulfur batteries (SSLSBs) with high energy density and high safety have attracted wide attention as they are one of the most promising energy storage devices to meet future market requirements. However, the development of SSLSBs faces various challenges due to the unreasonable structural design in sulfur cathodes. Carbon is one of the indispensable components in sulfur cathodes. The rational design of carbon materials becomes an important strategy to address the challenges in sulfur cathodes. This review summarizes recent literature about the design and application of carbon materials for sulfur cathodes in inorganic-based SSLSBs. It starts with the introduction of different carbon materials from zero-dimensional (0D) to three-dimensional (3D) carbon materials. Particularly, this review paper highlights the structural design of carbon materials and the cathode fabrication methods, toward improving the conductivity of cathodes, buffering volume changes in cathodes, reducing interfacial resistance among cathode components, and increasing the mass loading of active materials. Finally, the existing challenges and promising solutions for carbon materials in the cathodes are discussed and proposed.
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    Urea-choline chloride deep eutectic solvent-assisted synthesis of luminescent nitrogen-doped carbon dots from chitin and their photocatalytic application in decolourizing malachite green
    (Canadian Science Publishing, 2023-04-20) Valencia, Hannah; Yeboah, Alfred; Turita, Steve; Muñoz, Kyle Joshua; Gaje, Arnold C.; Siva, Chenille Rose; Paige, Matthew F; Ponce, Concepcion Palangan
    Luminescent carbon dots (CDs) are emerging carbon nanomaterials whose tunable and exceptional optoelectronic properties have found applications as alternatives to traditional fluorophores and metal-based catalysts. Further, they can be easily prepared from biomass and using green solvents. Biomass sources of CDs, however, often result in the formation of thousands of products which are difficult to separate. In this study, CDs were synthesized using a urea-choline chloride deep eutectic solvent (DES) and shrimp shell-derived chitin as raw materials through a low temperature solvothermal treatment. This was followed by a facile liquid-liquid extraction with acetone to improve the optical properties and narrow the size distribution of the CDs. The acetone-extracted CDs (ACDs) showed good performance in photocatalytic degradation of the aquatic pollutant, malachite green. They also show good potential in monitoring various toxic water pollutants through the quenching effect of selected pesticides, antibiotics, heavy metals and anions on the fluorescence of ACDs.
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    A Comparative Study of Boron-Containing and Boron-Omitted Capsaicinoids
    (Canadian Science Publishing, 2023-04-30) Ngô, Giao N.; Park, SunMin; Stack, Hailey M.; Rourke, Jillian; Melanson, Jennifer; Westcott, Stephen A.
    This study reports the synthesis and characterization of a limited number of novel boron-containing and boron-omitted capsaicinoids, providing 12 unique substrates. We have previously reported boron-containing capsaicinoids that showed improved bioactivity compared to capsaicin itself but have yet to test a series of analogous boron-omitted substrates as a direct comparison. The boron-containing capsaicinoids bear a pinacolboronate ester (Bpin) group, which was incorporated using an iridium catalyzed hydroboration reaction. We report that although nearly all compounds display moderate cytotoxic activity that bests that of capsaicin against human colon HCT116 cancer cells, the activity of our boron-omitted capsaicinoids surpasses that of the boron-containing analogues.
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    Solar Cell of Sb2O3:CuO/Si Prepared Via Thermal Evaporation Technique: Structural, Morphological Properties, and Efficiency
    (Canadian Science Publishing, 2023-03-25) Attia, Ali; Shakir, Foaad; Abass, Khalid Haneen
    Antimonous oxide (Sb2O3) has intriguing physical and chemical features that make it useful in various device applications, including solar cells. Nanofilms of Sb2O3:0.02wt.% CuO were prepared onto glass and silicon substrates etched by laser using a thermal evaporation process in a vacuum, with different thicknesses of about (20, 30, and 40 nm). The deposited nanofilms have no distinguishing peaks in XRD analysis. The broadening of the peak shows due to the absence of long-range symmetry as a result, the nanocrystalline structure is disorganized. SEM analysis of the surface morphology of the formed nanofilms showed spread out uniformly and were devoid of islands and voids. The particles were all about the same size, and the new structures were created with a thickness of 40 nm. AFM scanning images showed the nanofilms' homogeneous surface morphology with granular shape. As nanofilm thickness increased, so was average roughness, root mean square value and grain diameter. Optical characteristics revealed a reduction in the transmittance spectrum with increasing thicknesses. Instead, the optical energy gap (E_g^opt) was decreased by quantum confinement from 3.56 to 3.48 eV. The electrical properties of the nanofilms were analyzed, and it was found that all were n-type and that mobility (µ) decreased with nanofilm thickness. As shown by the I-V characteristics, the solar cell's conversion efficiency increases to (6.373%) at power = 100 mW/cm2 with (0.138) filling factor, (4V) of open circuit voltage, and (2.6 mA) of short circuit.
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    The Corrosion Effect of Dynamic Liquid Metal Galinstan on Stainless Steel S31600/SS316 in the Presence of Selected Refrigerants at Temperatures up to 150 °C
    (Canadian Science Publishing, 2023-03-31) Wu, Lijun; Geddis, Philip; Liu, Kun; Hiscocks, Jessica; Courchesne, William
    A corrosion study examined stainless steel S31600/SS316 after exposure to the liquid metal galinstan and gases including nitrogen, n-pentane, isobutane and R245fa at 150 °C under dynamic conditions for 3.5, 9.5 and 20.5 days. Ampules partly filled with galinstan and the gas were continuously stirred to create regions of gas-only, gas-liquid, and liquid-only exposure. Post test examinations used a variety of qualitative and quantitative methods (visual observation, scanning electron microscopy with energy dispersive X-ray spectroscopy, surface profilometry and chemical analysis) to evaluate coupons and galinstan samples for evidence of corrosion. In the gas-exposed region, no corrosion was detected in any coupon. In the liquid region, galinstan constituents were found to be localized to grain boundaries for nitrogen and isobutane coupons but dispersed on n-pentane coupons; a gallium oxide layer was found on R245fa coupons. In the liquid-gas interface region, severe corrosion was found on the n-pentane 20.5-day and the isobutane 9.5 and 20.5-day coupons; fine scattered corrosion on the R245fa 9.5-day coupon but not on the 20.5-day coupon was observed. Profilometry results indicated the least roughness change for coupons in n-pentane, a higher change in nitrogen, then in isobutane, and the highest in R245fa. In the presence of refrigerants and under dynamic conditions, intergranular attack on stainless steel may be enhanced by chemical reactions combined with microsegregation of galinstan or gallium oxide elements on stainless steel grain boundaries. Further work is required to confidently identify and explain this corrosion mechanism.
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    Dodecyltrimethylammonium bromide-styrene microemulsion dielectric investigation in aqueous media
    (Canadian Science Publishing, 2023-01-17) Rohman, Nashiour; Mohiuddin, Tariq; Khan, Imran
    In this paper, we report the complex permittivity of aqueous microemulsions of N-dodecyltrimethylammonium bromide and styrene. The studies were carried out at 298.15 K while varying the styrene to surfactant concentration ratio, S_0 (0.16  So  0.71) and the surfactant concentration, c (0.1032 c (mol•dm-3 )  0.7806). The frequencies ranged from 100 MHz to 89 GHz. An analysis of a particular solution is conducted over the temperature range of 278.15 to 328.15K in order to calculate the energy of the activation parameters. At 298.15 K, the spectra are fitted to a total of five Debye processes for concentration dependency series and three Debye processes for temperature dependence series. Br- surface and bulk diffusion surrounding the micelles best describes the two low frequency dispersions, at 100 MHz and 0.8 GHz, respectively. These mechanisms were examined using Grosse theory. The Maxwell-Wagner relaxation process is equivalent to high frequency micelle dispersion at 0.8 GHz. The thickness of the conducting shell of the micelle is determined by using the electrical conductivity of the particles and parameters taken from the Grosse theory, and the results are comparable to those from an examination of the Pauly and Schwan model. The Grosse model and solvent dispersion analysis were used to calculate the volume fractions of micelles. Both approaches were in agreement. The surfactant head group non-rotationally hydrates almost 7±1 water molecules. Styrene addition allows for the non-rotationally bound accommodation of an additional 7±1 water molecules.
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    Active Learning for Optimum Experimental Design – Insight into Perovskite Oxides
    (Canadian Science Publishing, 2023-02-10) Lourenco, Maicon Pierre; Tchagang, Alain; Shankar, Karthik; Thangadurai, Venkataraman; Salahub, Dennis R.
    Finding the optimum material with improved properties for a given application is challenging because data acquisition in materials science and chemistry is time consuming and expensive. Therefore, dealing with small datasets is a reality in chemistry, whether the data is obtained from synthesis or computational experiments. In this work, we propose a new artificial intelligence method based on active learning (AL) to guide new experiments with as little data as possible, for optimum experimental design. The AL method is applied to ABO3 perovskites where a descriptor based on atomic properties was developed. Several regressor algorithms were employed: artificial neural network, Gaussian process and support vector regressor. The developed AL method was applied in the experimental design of two important materials: non-stoichiometric perovskites (Ba(1-x)AxTi(1-y)ByO3) due to substituting ionic sites with different concentrations and elements (A = Ca, Sr, Cd; B = Zr, Sn, Hf), aiming at the maximization of the energy storage density; stoichiometric ABO3 perovskites where different elements are changed in the A and B sites for the minimization of the formation energy. AL for experimental design is implemented in the machine learning agent for chemistry and design (MLChem4D) software; which has the potential to be applied in inorganic and organic synthesis (e.g.: search for the optimum concentrations, catalysts, reactants, temperatures and pH to improve the yield) and materials science (e.g.: search the periodic table for the proper elements and their concentrations to improve the materials properties). The latter marks the first MLChem4D application for the design of perovskites.
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    Dicarbon defect in hexagonal boron nitride monolayer - a theoretical study
    (Canadian Science Publishing, 2023-01-11) Korona, Tatiana; Jankowska, Joanna; Masoumifeshani, Emran
    A comprehensive theoretical study of the lowest electronic vertical excitations of the CBCN defect in the monolayer of hexagonal boron nitride has been performed. Both the periodic boundary conditions approach and the finite-cluster simulation of the defect have been utilized at the density-functional theory (DFT) level. Clusters of increasing sizes have been used in order to estimate artefacts resulting from edge effects. The stability of the results with respect to several density functionals and various basis sets has been also examined. High-level ab initio calculations with methods like EOM-CCSD, ADC(2), and TD-CC2, were performed for the smallest clusters. It turns out that TD-DFT with the CAM-B3LYP functional gives similar lowest excitation energies as EOM-CCSD, ADC(2), and TD-CC2. The lowest excitation energies resulting from the periodic-boundary calculation utilizing the Bethe-Salpeter equation are in agreement with the results for finite clusters. The analysis of important configurations and transition densities shows that for all studied methods, the lowest excited state is localized on two carbon atoms and their closest neighbours and has a large dipole transition moment. The optimized geometries for the lowest two excited states indicate that in both cases the carbon-carbon bond becomes a single bond, while for the second excited state additionally one from boron-nitrogen bonds looses its partially double character. The calculation of the excitation energies at the respective optimal geometry reveals that these two energies become about 0.5 eV lower than vertical excitations from the ground-state geometry.
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    Grid-based state space exploration for molecular binding
    (Canadian Science Publishing, 2023-01-27) Zupan, Hana; Heinz, Frederick; Keller, Bettina G.
    Binding processes are difficult to sample with molecular-dynamics (MD) simulations. In particular, the state space exploration is often incomplete. Evaluating the molecular interaction energy on a grid circumvents this problem but is heavily limited by state space dimensionality. Here, we make the first steps towards a low-dimensional grid-based model of molecular binding. We discretise the state space of relative positions and orientations of the two molecules under the rigid body assumption. The corresponding program is published as the Python package molgri. For the rotational component of the grids, we test algorithms based on Euler angles, polyhedra and quaternions, of which the polyhedra-based are the most uniform. The program outputs a sequence of molecular structures that can be easily processed by standard MD programs to calculate grid point energies. We demonstrate the grid-based approach on two molecular systems: a water dimer and a coiled-coil protein interacting with a chloride anion. For the second system we relax the rigid-body assumption and improve the accuracy of the grid point energies by an energy minimisation. In both cases, oriented bonding patterns and energies confirm expectations from chemical intuition and MD simulations. We also demonstrate how analysis of energy contributions on a grid can be performed and demonstrate that electrostatically-driven association is sufficiently resolved by point-energy calculations. Overall, grid-based models of molecular binding are potentially a powerful complement to molecular sampling approaches, and we see the potential to expand the method to quantum chemistry and flexible docking applications.
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    Synthesis of Novel 2- and 8-Substituted 4-Amino-7-chloroquinolines and their N-Alkylated Coupling Products
    (Canadian Science Publishing, 2023-03-08) Nemez, Dion B; Sidhu, Baldeep K; Carlin, Kevin; Friesen, Albert; Herbert, David E.
    The synthesis of a series of 2- and 8-substituted 4-amino-7-chloroquinolines is presented. The chloro in the 7-position can be effectively substituted using amino alcohols to yield novel analogues of the antimalarial (hydroxy)chloroquine. Both short chain (2-aminoethanol) and long chain (5-[N-ethyl-N-(2-hydroxyethyl)amino]-2-aminopentane) coupling partners can be used. While ketone and nitro functionalities were found to be incompatible with the coupling conditions, electron-donating amino and dimethylamino substituents were tolerated. In addition to characterization in solution using multinuclear NMR spectroscopy and high-resolution mass spectrometry, single-crystal X-ray structures are presented of two 4,7-dichloroquinolines as well as three of the N-alkylated products including a unique species in which a pyrrole heterocycle formed at the 2-position of the quinoline sub-unit and a rare example of a 4-aza-1,10-phenanthroline.
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    When is a Pyridine Not a Pyridine? Benzannulated N-Heterocyclic Ligands in Molecular Materials Chemistry
    (Canadian Science Publishing, 2023-01-27) Herbert, David E.
    The C=N bond is a critical structural piece of many N-donor ligand scaffolds and is central to the properties and reactivity of important coordination complexes. For example, C=N units play a key role in the ‘redox non-innocence’ of α-diimine complexes and in making charge-transfer excited-state character available to complexes of N-heterocyclic ligands such as bipyridine. In N-heterocycles like pyridine, benzannulation can be used to extend the conjugated C=N containing π-system to quinoline (2,3-benzopyridine) to acridine (2,3-benzoquinoline). This stabilizes the lowest unoccupied molecular orbital (LUMO) of the molecule and boosts its electron-accepting properties, but the position of the benzannulation matters. For example, phenanthridine (3,4-benzoquinoline), an asymmetric isomer of acridine, bears a similarly electronically accessible extended π-system but more chemically isolated, ‘imine-like’ C=N moiety. This Award Paper presents an overview of our work investigating the impact of such site-selective benzannulation on the chemistry and properties of phenanthridine as a molecule and ligand.
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    Gathering Validity Evidence in the Development of a New Version of the Attitude Toward the Subject of Chemistry Inventory (ASCI-UE)
    (Canadian Science Publishing, 2023-01-20) Rocabado, Guizella Amalia; Hernandez Montes, Lilian; Ferreira, Roberto A.; Rodríguez, Cristina; Lewis, Jennifer E
    Organic chemistry is one of the most feared and failed courses due to its complex and fast-paced nature. Investigating affective metrics that relate to achievement in these courses can be worthwhile, particularly when these metrics show predictive relationships to achievement. Attitude toward chemistry has been investigated utilizing a variety of instruments. We present herein an instrument related to the well-established ASCIv2. This new instrument was developed utilizing The Standards of Psychological and Educational Measurement which describe five aspects of validity evidence that should be gathered when using instruments in research. Content validity was gathered through consultation with experts. Response process validity was gathered through student interviews. Internal structure validity was collected through confirmatory factor analysis. Relations to other variables were investigated through correlation analysis and structural equation modeling. Consequential validity was studied through measurement invariance testing before comparing scores for subgroups (high- and low-achieving students). Additionally, reliability evidence was tested with Omega coefficients for each of the factors. We showed that all tests and analyses were done with high rigor, and that this new instrument, ASCI-UE, measuring Utility and Emotional Satisfaction, can provide interesting results and implications for research and practice.
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    Efficient simulation of multielectron dynamics in molecules under intense laser pulses: Implementation of the multiconfiguration time-dependent Hartree-Fock method based on the adaptive finite element method
    (Canadian Science Publishing, 2023-01-27) Orimo, Yuki; Sato, Takeshi; Ishikawa, Kenichi L.
    We present an implementation of the multiconfiguration time-dependent Hartree-Fock method based on the adaptive finite element method for molecules under intense laser pulses. For efficient simulations, orbital functions are propagated by a stable propagator using the short iterative Arnoldi scheme and our implementation is parallelized for distributed memory computing. This is demonstrated by simulating high-harmonic generation from a water molecule and achieves a simulation of multielectron dynamics with overwhelmingly less computational time, compared to our previous work. [R. Sawada, et al., Phys. Rev. A 93, 023434 (2016).].