Commenced in January 2007
Frequency: Monthly
Edition: International
Paper Count: 537

Search results for: alkyne-azide click chemistry (CuAAC)

537 Polymer-Nanographite Nanocomposites for Biosensor Applications

Authors: Payal Mazumdar, Sunita Rattan, Monalisa Mukherjee


Polymer nanocomposites are a special class of materials having unique properties and wide application in diverse areas such as EMI shielding, sensors, photovoltaic cells, membrane separation properties, drug delivery etc. Recently the nanocomposites are being investigated for their use in biomedical fields as biosensors. Though nanocomposites with carbon nanoparticles have received worldwide attention in the past few years, comparatively less work has been done on nanographite although it has in-plane electrical, thermal and mechanical properties comparable to that of carbon nanotubes. The main challenge in the fabrication of these nanocomposites lies in the establishment of homogeneous dispersion of nanographite in polymer matrix. In the present work, attempts have been made to synthesize the nanocomposites of polystyrene and nanographite using click chemistry. The polymer and the nanographite are functionalized prior to the formation of nanocomposites. The polymer, polystyrene, was functionalized with alkyne moeity and nanographite with azide moiety. The fabricating of the nanocomposites was accomplished through click chemistry using Cu (I)-catalyzed Huisgen dipolar cycloaddition. The functionalization of filler and polymer was confirmed by NMR and FTIR. The nanocomposites formed by the click chemistry exhibit better electrical properties and the sensors are evaluated for their application as biosensors.

Keywords: nanocomposites, click chemistry, nanographite, biosensor

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536 Reactions of 4-Aryl-1H-1,2,3-Triazoles with Cycloalkenones and Epoxides: Synthesis of 2,4- and 1,4-Disubstituted 1,2,3-Triazoles

Authors: Ujjawal Kumar Bhagat, Kamaluddin, Rama Krishna Peddinti


The Huisgen’s 1,3-dipolar [3+2] cycloaddition of organic azides and alkynes often give the mixtures of both the regioisomers 1,4- and 1,5- disubstituted 1,2,3-triazoles. Later, in presence of metal salts (click chemistry) such as copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) was used for the synthesis of 1,4-disubstituted 1,2,3-triazoles as a sole products regioselectively. Also, the ‘click reactions’ of Ruthenium-catalyzed azides-alkynes cycloaddition (RuAAC) is used for the synthesis of 1,5-disubstituted 1,2,3-triazoles as a single isomer. The synthesis of 1,4- and 1.5-disubstituted 1,2,3-triazoles has become the gold standard of ‘click chemistry’ due to its reliability, specificity, and biocompatibility. The 1,4- and 1,5-disubstituted 1,2,3-triazoles have emerged as one of the most powerful entities in the varieties of biological properties like antibacterial, antitubercular, antitumor, antifungal and antiprotozoal activities. Some of the 1,4,5-trisubstituted 1,2,3-triazoles exhibit Hsp90 inhibiting properties. The 1,4-disubstituted 1,2,3-triazoles also play a big role in the area of material sciences. The triazole-derived oligomeric, polymeric structures are the potential materials for the preparation of organic optoelectronics, silicon elastomers and unimolecular block copolymers. By the virtue of hydrogen bonding and dipole interactions, the 1,2,3-triazole moiety readily associates with the biological targets. Since, the 4-aryl-1H-1,2,3-triazoles are stable entities, they are chemically robust and very less reactive. In this regard, the addition of 4-aryl-1H-1,2,3-triazoles as nucleophiles to α,β-unsaturated carbonyls and nucleophilic substitution with the epoxides constitutes a powerful and challenging synthetic approach for the generation of disubstituted 1,2,3-triazoles. Herein, we have developed aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones in the presence of an organic base (DABCO) in acetonotrile solvent leading to the formation of disubstituted 1,2,3-triazoles. The reaction provides 1,4-disubstituted triazoles, 3-(4-aryl-1H-1,2,3-triazol-1-yl)cycloalkanones in major amount along with 1,5-disubstituted 1,2,3-triazoles, minor regioisomers with excellent combined chemical yields (upto99%). The nucleophilic behavior of 4-aryl-1H-1,2,3-triazoles was also tested in the ring opening of meso-epoxides in the presence of organic bases (DABCO/Et3N) in acetonotrile solvent furnishing the two regioisomers1,4- and 1,5-disubstituted 1,2,3-triazoles. Thus, the novelty of this methodology is synthesis of diversified disubstituted 1,2,3-triazoles under metal free condition.The results will be presented in detail.

Keywords: aza-Michael addition, cycloalkenones, epoxides, triazoles

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535 Synthesis of Star Compounds Bearing a Porphyrin Core and Cholic Acid Units by Using Click Chemistry: Study of the Optical Properties and Aggregation

Authors: Edgar Aguilar-Ortíz, Nicolas Lévaray, Mireille Vonlanthen, Eric G. Morales-Espinoza, Ernesto Rivera, Xiao Xia Zhu


Four new star compounds bearing a porphyrin core and cholic acid units, (TPPh(Zn) tetra-CA, TPPh(2H) tetra-CA, TPPh(Zn) octa-CA and TPPh(2H) octa-CA), have been synthesized using the Click Chemistry approach, which consist on azide-alkyne couplings. These novel functionalized porphyrins were characterized by 1H and 13C NMR spectroscopy and their structure was confirmed by MALDI-TOF. The optical properties of these compounds were studied by absorption and fluorescence spectroscopy. On the other hand, order to evaluate the amphiphilic properties of the cholic acid units combined with the optical response of the porphyrin core, we performed absorption and fluorescence studies in function of the polarity of the environment. It was found that as soon as we increase the polarity of the solvent, the Zn-metallated porphyrins, (TPPh(Zn) tetra-CA and TPPh(Zn) octa-CA), are able to form J aggregates, whereas the free-base porphyrins, TPPh(2H) tetra-CA and TPPh(2H) octa-CA, behaved differently.

Keywords: aggregates, amphiphilic, cholic acid, click-chemistry, porphyrin

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534 Using Neural Networks for Click Prediction of Sponsored Search

Authors: Afroze Ibrahim Baqapuri, Ilya Trofimov


Sponsored search is a multi-billion dollar industry and makes up a major source of revenue for search engines (SE). Click-through-rate (CTR) estimation plays a crucial role for ads selection, and greatly affects the SE revenue, advertiser traffic and user experience. We propose a novel architecture of solving CTR prediction problem by combining artificial neural networks (ANN) with decision trees. First, we compare ANN with respect to other popular machine learning models being used for this task. Then we go on to combine ANN with MatrixNet (proprietary implementation of boosted trees) and evaluate the performance of the system as a whole. The results show that our approach provides a significant improvement over existing models.

Keywords: neural networks, sponsored search, web advertisement, click prediction, click-through rate

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533 Preparation of Allyl BODIPY for the Click Reaction with Thioglycolic Acid

Authors: Chrislaura Carmo, Luca Deiana, Mafalda Laranjo, Abilio Sobral, Armando Cordova


Photodynamic therapy (PDT) is currently used for the treatment of malignancies and premalignant tumors. It is based on the capture of a photosensitizing molecule (PS) which, when excited by light at a certain wavelength, reacts with oxygen and generates oxidizing species (radicals, singlet oxygen, triplet species) in target tissues, leading to cell death. BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indaceno) derivatives are emerging as important candidates for photosensitizer in photodynamic therapy of cancer cells due to their high triplet quantum yield. Today these dyes are relevant molecules in photovoltaic materials and fluorescent sensors. In this study, it will be demonstrated the possibility that BODIPY can be covalently linked to thioglycolic acid through the click reaction. Thiol−ene click chemistry has become a powerful synthesis method in materials science and surface modification. The design of biobased allyl-terminated precursors with high renewable carbon content for the construction of the thiol-ene polymer networks is essential for sustainable development and green chemistry. The work aims to synthesize the BODIPY (10-(4-(allyloxy) phenyl)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-dipyrrolo[1,2-c:2',1'-f] [1,3,2] diazaborinin-4-ium-5-uide) and to click reaction with Thioglycolic acid. BODIPY was synthesized by the condensation reaction between aldehyde and pyrrole in dichloromethane, followed by in situ complexation with BF3·OEt2 in the presence of the base. Then it was functionalized with allyl bromide to achieve the double bond and thus be able to carry out the click reaction. The thiol−ene click was performed using DMPA (2,2-Dimethoxy-2-phenylacetophenone) as a photo-initiator in the presence of UV light (320–500 nm) in DMF at room temperature for 24 hours. Compounds were characterized by standard analytical techniques, including UV-Vis Spectroscopy, 1H, 13C, 19F NMR and mass spectroscopy. The results of this study will be important to link BODIPY to polymers through the thiol group offering a diversity of applications and functionalization. This new molecule can be tested as third-generation photosensitizers, in which the dye is targeted by antibodies or nanocarriers by cells, mainly in cancer cells, PDT and Photodynamic Antimicrobial Chemotherapy (PACT). According to our studies, it was possible to visualize a click reaction between allyl BODIPY and thioglycolic acid. Our team will also test the reaction with other thiol groups for comparison. Further, we will do the click reaction of BODIPY with a natural polymer linked with a thiol group. The results of the above compounds will be tested in PDT assays on various lung cancer cell lines.

Keywords: bodipy, click reaction, thioglycolic acid, allyl, thiol-ene click

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532 Synthesis of Fluorescent PET-Type “Turn-Off” Triazolyl Coumarin Based Chemosensors for the Sensitive and Selective Sensing of Fe⁺³ Ions in Aqueous Solutions

Authors: Aidan Battison, Neliswa Mama


Environmental pollution by ionic species has been identified as one of the biggest challenges to the sustainable development of communities. The widespread use of organic and inorganic chemical products and the release of toxic chemical species from industrial waste have resulted in a need for advanced monitoring technologies for environment protection, remediation and restoration. Some of the disadvantages of conventional sensing methods include expensive instrumentation, well-controlled experimental conditions, time-consuming procedures and sometimes complicated sample preparation. On the contrary, the development of fluorescent chemosensors for biological and environmental detection of metal ions has attracted a great deal of attention due to their simplicity, high selectivity, eidetic recognition, rapid response and real-life monitoring. Coumarin derivatives S1 and S2 (Scheme 1) containing 1,2,3-triazole moieties at position -3- have been designed and synthesized from azide and alkyne derivatives by CuAAC “click” reactions for the detection of metal ions. These compounds displayed a strong preference for Fe3+ ions with complexation resulting in fluorescent quenching through photo-induced electron transfer (PET) by the “sphere of action” static quenching model. The tested metal ions included Cd2+, Pb2+, Ag+, Na+, Ca2+, Cr3+, Fe3+, Al3+, Cd2+, Ba2+, Cu2+, Co2+, Hg2+, Zn2+ and Ni2+. The detection limits of S1 and S2 were determined to be 4.1 and 5.1 uM, respectively. Compound S1 displayed the greatest selectivity towards Fe3+ in the presence of competing for metal cations. S1 could also be used for the detection of Fe3+ in a mixture of CH3CN/H¬2¬O. Binding stoichiometry between S1 and Fe3+ was determined by using both Jobs-plot and Benesi-Hildebrand analysis. The binding was shown to occur in a 1:1 ratio between the sensor and a metal cation. Reversibility studies between S1 and Fe3+ were conducted by using EDTA. The binding site of Fe3+ to S1 was determined by using 13 C NMR and Molecular Modelling studies. Complexation was suggested to occur between the lone-pair of electrons from the coumarin-carbonyl and the triazole-carbon double bond.

Keywords: chemosensor, "click" chemistry, coumarin, fluorescence, static quenching, triazole

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531 Comparison of Interactive Performance of Clicking Tasks Using Cursor Control Devices under Different Feedback Modes

Authors: Jinshou Shi, Xiaozhou Zhou, Yingwei Zhou, Tuoyang Zhou, Ning Li, Chi Zhang, Zhanshuo Zhang, Ziang Chen


In order to select the optimal interaction method for common computer click tasks, the click experiment test adopts the ISO 9241-9 task paradigm, using four common operations: mouse, trackball, touch, and eye control under visual feedback, auditory feedback, and no feedback. Through data analysis of various parameters of movement time, throughput, and accuracy, it is found that the movement time of touch-control is the shortest, the operation accuracy and throughput are higher than others, and the overall operation performance is the best. In addition, the motion time of the click operation with auditory feedback is significantly lower than the other two feedback methods in each operation mode experiment. In terms of the size of the click target, it is found that when the target is too small (less than 14px), the click performance of all aspects is reduced, so it is proposed that the design of the interface button should not be less than 28px. In this article, we discussed in detail the advantages and disadvantages of the operation and feedback methods, and the results of the discussion of the click operation can be applied to the design of the buttons in the interactive interface.

Keywords: cursor control performance, feedback, human computer interaction, throughput

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530 Surface Sunctionalization Strategies for the Design of Thermoplastic Microfluidic Devices for New Analytical Diagnostics

Authors: Camille Perréard, Yoann Ladner, Fanny D'Orlyé, Stéphanie Descroix, Vélan Taniga, Anne Varenne, Cédric Guyon, Michael. Tatoulian, Frédéric Kanoufi, Cyrine Slim, Sophie Griveau, Fethi Bedioui


The development of micro total analysis systems is of major interest for contaminant and biomarker analysis. As a lab-on-chip integrates all steps of an analysis procedure in a single device, analysis can be performed in an automated format with reduced time and cost, while maintaining performances comparable to those of conventional chromatographic systems. Moreover, these miniaturized systems are either compatible with field work or glovebox manipulations. This work is aimed at developing an analytical microsystem for trace and ultra trace quantitation in complex matrices. The strategy consists in the integration of a sample pretreatment step within the lab-on-chip by a confinement zone where selective ligands are immobilized for target extraction and preconcentration. Aptamers were chosen as selective ligands, because of their high affinity for all types of targets (from small ions to viruses and cells) and their ease of synthesis and functionalization. This integrated target extraction and concentration step will be followed in the microdevice by an electrokinetic separation step and an on-line detection. Polymers consisting of cyclic olefin copolymer (COC) or fluoropolymer (Dyneon THV) were selected as they are easy to mold, transparent in UV-visible and have high resistance towards solvents and extreme pH conditions. However, because of their low chemical reactivity, surface treatments are necessary. For the design of this miniaturized diagnostics, we aimed at modifying the microfluidic system at two scales : (1) on the entire surface of the microsystem to control the surface hydrophobicity (so as to avoid any sample wall adsorption) and the fluid flows during electrokinetic separation, or (2) locally so as to immobilize selective ligands (aptamers) on restricted areas for target extraction and preconcentration. We developed different novel strategies for the surface functionalization of COC and Dyneon, based on plasma, chemical and /or electrochemical approaches. In a first approach, a plasma-induced immobilization of brominated derivatives was performed on the entire surface. Further substitution of the bromine by an azide functional group led to covalent immobilization of ligands through “click” chemistry reaction between azides and terminal alkynes. COC and Dyneon materials were characterized at each step of the surface functionalization procedure by various complementary techniques to evaluate the quality and homogeneity of the functionalization (contact angle, XPS, ATR). With the objective of local (micrometric scale) aptamer immobilization, we developed an original electrochemical strategy on engraved Dyneon THV microchannel. Through local electrochemical carbonization followed by adsorption of azide-bearing diazonium moieties and covalent linkage of alkyne-bearing aptamers through click chemistry reaction, typical dimensions of immobilization zones reached the 50 µm range. Other functionalization strategies, such as sol-gel encapsulation of aptamers, are currently investigated and may also be suitable for the development of the analytical microdevice. The development of these functionalization strategies is the first crucial step in the design of the entire microdevice. These strategies allow the grafting of a large number of molecules for the development of new analytical tools in various domains like environment or healthcare.

Keywords: alkyne-azide click chemistry (CuAAC), electrochemical modification, microsystem, plasma bromination, surface functionalization, thermoplastic polymers

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529 Synthesis and Pharmaco-Potential Evaluation of Quinoline Hybrids

Authors: Paul Awolade, Parvesh Singh


The global threat of pathogenic resistance to available therapeutic agents has become a menace to clinical practice, public health and man’s existence inconsequential. This has therefore led to an exigency in the development of new molecular scaffolds with profound activity profiles. In this vein, a versatile synthetic tool for accessing new molecules by incorporating two or more pharmacophores into a single entity with the unique ability to be recognized by multiple receptors hence leading to an improved bioactivity, known as molecular hybridization, has been explored with tremendous success. Accordingly, aware of the similarity in pharmacological activity spectrum of quinoline and 1,2,3-triazole pharmacophores such as; anti-Alzheimer, anticancer, anti-HIV, antimalarial and antimicrobial to mention but a few, the present study sets out to synthesize hybrids of quinoline and 1,2,3-triazole. The hybrids were accessed via click chemistry using copper catalysed azide-alkyne 1,3-dipolar cycloaddition reaction. All synthesized compounds were evaluated for their pharmaco-potential in an antimicrobial assay out of which the 3-OH derivative emerged as the most active with MIC value of 4 μg/mL against Cryptococcus neoformans; a value superior to standard Fluconazole and comparable to Amphotericin B. Structures of synthesized hybrids were elucidated using appropriate spectroscopic techniques (1H, 13C and 2D NMR, FT-IR and HRMS).

Keywords: bioisostere, click chemistry, molecular hybridization, quinoline, 1, 2, 3-triazole

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528 Tracing Digital Traces of Phatic Communion in #Mooc

Authors: Judith Enriquez-Gibson


This paper meddles with the notion of phatic communion introduced 90 years ago by Malinowski, who was a Polish-born British anthropologist. It explores the phatic in Twitter within the contents of tweets related to moocs (massive online open courses) as a topic or trend. It is not about moocs though. It is about practices that could easily be hidden or neglected if we let big or massive topics take the lead or if we simply follow the computational or secret codes behind Twitter itself and third party software analytics. It draws from media and cultural studies. Though at first it appears data-driven as I submitted data collection and analytics into the hands of a third party software, Twitonomy, the aim is to follow how phatic communion might be practised in a social media site, such as Twitter. Lurking becomes its research method to analyse mooc-related tweets. A total of 3,000 tweets were collected on 11 October 2013 (UK timezone). The emphasis of lurking is to engage with Twitter as a system of connectivity. One interesting finding is that a click is in fact a phatic practice. A click breaks the silence. A click in one of the mooc website is actually a tweet. A tweet was posted on behalf of a user who simply chose to click without formulating the text and perhaps without knowing that it contains #mooc. Surely, this mechanism is not about reciprocity. To break the silence, users did not use words. They just clicked the ‘tweet button’ on a mooc website. A click performs and maintains connectivity – and Twitter as the medium in attendance in our everyday, available when needed to be of service. In conclusion, the phatic culture of breaking silence in Twitter does not have to submit to the power of code and analytics. It is a matter of human code.

Keywords: click, Twitter, phatic communion, social media data, mooc

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527 Dipeptide Functionalized Nanoporous Anodic Aluminium Oxide Membrane for Capturing Small Molecules

Authors: Abdul Mutalib Md Jani, Abdul Hadi Mahmud, Mohd Tajuddin Mohd Ali


The rapid growth of interest in surface modification of nanostructures materials that exhibit improved structural and functional properties is attracting more researchers. The unique properties of highly ordered nanoporous anodic aluminium oxide (NAAO) membrane have been proposed as a platform for biosensing applications. They exhibit excellent physical and chemical properties with high porosity, high surface area, tunable pore sizes and excellent chemical resistance. In this study, NAAO was functionalized with 3-aminopropyltriethoxysilane (APTES) to prepared silane-modified NAAO. Amine functional groups are formed on the surface of NAAO during silanization and were characterized using Fourier Transform Infrared spectroscopy (FTIR). The synthesis of multi segment of peptide on NAAO surfaces can be realized by changing the surface chemistry of the NAAO membrane via click chemistry. By click reactions, utilizing alkyne terminated with amino group, various peptides tagged on NAAO can be envisioned from chiral natural or unnatural amino acids using standard coupling methods (HOBt, EDCI and HBTU). This strategy seemly versatile since coupling strategy of dipeptide with another amino acids, leading to tripeptide, tetrapeptide or pentapeptide, can be synthesized without purification. When an appropriate terminus is selected, multiple segments of amino acids can be successfully synthesized on the surfaces. The immobilized NAAO should be easily separated from the reaction medium by conventional filtration, thus avoiding complicated purification methods. Herein, we proposed to synthesize multi fragment peptide as a model for capturing and attaching various small biomolecules on NAAO surfaces and can be also applied as biosensing device, drug delivery systems and biocatalyst.

Keywords: nanoporous anodic aluminium oxide, silanization, peptide synthesise, click chemistry

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526 Evaluating the Location of Effective Product Advertising on Facebook Ads

Authors: Aulia F. Hadining, Atya Nur Aisha, Dimas Kurninatoro Aji


Utilization of social media as a marketing tool is growing rapidly, including for SMEs. Social media allows the user to give product evaluation and recommendations to the public. In addition, the social media facilitate word-of-mouth marketing communication. One of the social media that can be used is Facebook, with Facebook Ads. This study aimed to evaluate the location of Facebook Ads, to obtain an appropriate advertising design. There are three alternatives location consist of desktop, right-hand column and mobile. The effectiveness and efficiency of advertising will be measured based on advertising metrics such as reach, click, Cost per Click (CUC) and Unique Click-Through-Rate (UCTR). Facebook's Ads Manager was used for seven days, targeted by age (18-24), location (Bandung), language (Indonesia) and keywords. The result was 13,999 total reach, as well as 342 clicks. Based on the results of comparison using ANOVA, there was a significant difference for each placement location based on advertising metrics. Mobile location was chosen to be successful ads, because it produces the lowest CUC, amounting to Rp 691,- per click and 14% UCTR. Results of this study showed Facebook Ads was useful and cost-effective media to promote the product of SME, because it could be view by many people in the same time.

Keywords: marketing communication, social media, Facebook Ads, mobile location

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525 Fabrication of Highly Stable Low-Density Self-Assembled Monolayers by Thiolyne Click Reaction

Authors: Leila Safazadeh, Brad Berron


Self-assembled monolayers have tremendous impact in interfacial science, due to the unique opportunity they offer to tailor surface properties. Low-density self-assembled monolayers are an emerging class of monolayers where the environment-interfacing portion of the adsorbate has a greater level of conformational freedom when compared to traditional monolayer chemistries. This greater range of motion and increased spacing between surface-bound molecules offers new opportunities in tailoring adsorption phenomena in sensing systems. In particular, we expect low-density surfaces to offer a unique opportunity to intercalate surface bound ligands into the secondary structure of protiens and other macromolecules. Additionally, as many conventional sensing surfaces are built upon gold surfaces (SPR or QCM), these surfaces must be compatible with gold substrates. Here, we present the first stable method of generating low-density self assembled monolayer surfaces on gold for the analysis of their interactions with protein targets. Our approach is based on the 2:1 addition of thiol-yne chemistry to develop new classes of y-shaped adsorbates on gold, where the environment-interfacing group is spaced laterally from neighboring chemical groups. This technique involves an initial deposition of a crystalline monolayer of 1,10 decanedithiol on the gold substrate, followed by grafting of a low-packed monolayer on through a photoinitiated thiol-yne reaction in presence of light. Orthogonality of the thiol-yne chemistry (commonly referred to as a click chemistry) allows for preparation of low-density monolayers with variety of functional groups. To date, carboxyl, amine, alcohol, and alkyl terminated monolayers have been prepared using this core technology. Results from surface characterization techniques such as FTIR, contact angle goniometry and electrochemical impedance spectroscopy confirm the proposed low chain-chain interactions of the environment interfacing groups. Reductive desorption measurements suggest a higher stability for the click-LDMs compared to traditional SAMs, along with the equivalent packing density at the substrate interface, which confirms the proposed stability of the monolayer-gold interface. In addition, contact angle measurements change in the presence of an applied potential, supporting our description of a surface structure which allows the alkyl chains to freely orient themselves in response to different environments. We are studying the differences in protein adsorption phenomena between well packed and our loosely packed surfaces, and we expect this data will be ready to present at the GRC meeting. This work aims to contribute biotechnology science in the following manner: Molecularly imprinted polymers are a promising recognition mode with several advantages over natural antibodies in the recognition of small molecules. However, because of their bulk polymer structure, they are poorly suited for the rapid diffusion desired for recognition of proteins and other macromolecules. Molecularly imprinted monolayers are an emerging class of materials where the surface is imprinted, and there is not a bulk material to impede mass transfer. Further, the short distance between the binding site and the signal transduction material improves many modes of detection. My dissertation project is to develop a new chemistry for protein-imprinted self-assembled monolayers on gold, for incorporation into SPR sensors. Our unique contribution is the spatial imprinting of not only physical cues (seen in current imprinted monolayer techniques), but to also incorporate complementary chemical cues. This is accomplished through a photo-click grafting of preassembled ligands around a protein template. This conference is important for my development as a graduate student to broaden my appreciation of the sensor development beyond surface chemistry.

Keywords: low-density self-assembled monolayers, thiol-yne click reaction, molecular imprinting

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524 Estimating View-Through Ad Attribution from User Surveys Using Convex Optimization

Authors: Yuhan Lin, Rohan Kekatpure, Cassidy Yeung


In Digital Marketing, robust quantification of View-through attribution (VTA) is necessary for evaluating channel effectiveness. VTA occurs when a product purchase is aided by an Ad but without an explicit click (e.g. a TV ad). A lack of a tracking mechanism makes VTA estimation challenging. Most prevalent VTA estimation techniques rely on post-purchase in-product user surveys. User surveys enable the calculation of channel multipliers, which are the ratio of the view-attributed to the click-attributed purchases of each marketing channel. Channel multipliers thus provide a way to estimate the unknown VTA for a channel from its known click attribution. In this work, we use Convex Optimization to compute channel multipliers in a way that enables a mathematical encoding of the expected channel behavior. Large fluctuations in channel attributions often result from overfitting the calculations to user surveys. Casting channel attribution as a Convex Optimization problem allows an introduction of constraints that limit such fluctuations. The result of our study is a distribution of channel multipliers across the entire marketing funnel, with important implications for marketing spend optimization. Our technique can be broadly applied to estimate Ad effectiveness in a privacy-centric world that increasingly limits user tracking.

Keywords: digital marketing, survey analysis, operational research, convex optimization, channel attribution

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523 One-Step Synthesis and Characterization of Biodegradable ‘Click-Able’ Polyester Polymer for Biomedical Applications

Authors: Wadha Alqahtani


In recent times, polymers have seen a great surge in interest in the field of medicine, particularly chemotherapeutics. One recent innovation is the conversion of polymeric materials into “polymeric nanoparticles”. These nanoparticles can be designed and modified to encapsulate and transport drugs selectively to cancer cells, minimizing collateral damage to surrounding healthy tissues, and improve patient quality of life. In this study, we have synthesized pseudo-branched polyester polymers from bio-based small molecules, including sorbitol, glutaric acid and a propargylic acid derivative to further modify the polymer to make it “click-able" with an azide-modified target ligand. Melt polymerization technique was used for this polymerization reaction, using lipase enzyme catalyst NOVO 435. This reaction was conducted between 90- 95 °C for 72 hours. The polymer samples were collected in 24-hour increments for characterization and to monitor reaction progress. The resulting polymer was purified with the help of methanol dissolving and filtering with filter paper then characterized via NMR, GPC, FTIR, DSC, TGA and MALDI-TOF. Following characterization, these polymers were converted to a polymeric nanoparticle drug delivery system using solvent diffusion method, wherein DiI optical dye and chemotherapeutic drug Taxol can be encapsulated simultaneously. The efficacy of the nanoparticle’s apoptotic effects were analyzed in-vitro by incubation with prostate cancer (LNCaP) and healthy (CHO) cells. MTT assays and fluorescence microscopy were used to assess the cellular uptake and viability of the cells after 24 hours at 37 °C and 5% CO2 atmosphere. Results of the assays and fluorescence imaging confirmed that the nanoparticles were successful in both selectively targeting and inducing apoptosis in 80% of the LNCaP cells within 24 hours without affecting the viability of the CHO cells. These results show the potential of using biodegradable polymers as a vehicle for receptor-specific drug delivery and a potential alternative for traditional systemic chemotherapy. Detailed experimental results will be discussed in the e-poster.

Keywords: chemotherapeutic drug, click chemistry, nanoparticle, prostat cancer

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522 Clicking Based Graphical Password Scheme Resistant to Spyware

Authors: Bandar Alahmadi


The fact that people tend to remember pictures better than texts, motivates researchers to develop graphical passwords as an alternative to textual passwords. Graphical passwords as such were introduced as a possible alternative to traditional text passwords, in which users prove their identity by clicking on pictures rather than typing alphanumerical text. In this paper, we present a scheme for graphical passwords that are resistant to shoulder surfing attacks and spyware attacks. The proposed scheme introduces a clicking technique to chosen images. First, the users choose a set of images, the images are then included in a grid where users can click in the cells around each image, the location of the click and the number of clicks are saved. As a result, the proposed scheme can be safe from shoulder surface and spyware attacks.

Keywords: security, password, authentication, attack, applications

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521 Synthesis of 5-Substituted 1H-Tetrazoles in Deep Eutectic Solvent

Authors: Swapnil A. Padvi, Dipak S. Dalal


The chemistry of tetrazoles has been grown tremendously in the past few years because tetrazoles are important and useful class of heterocyclic compounds which have a widespread application such as anticancer, antimicrobial, analgesics, antibacterial, antifungal, antihypertensive, and anti-allergic drugs in medicinal chemistry. Furthermore, tetrazoles have application in material sciences as explosives, rocket propellants, and in information recording systems. In addition to this, they have a wide range of application in coordination chemistry as a ligand. Deep eutectic solvents (DES) have emerged over the current decade as a novel class of green reaction media and applied in various fields of sciences because of their unique physical and chemical properties similar to the ionic liquids such as low vapor pressure, non-volatility, high thermal stability and recyclability. In addition, the reactants of DES are cheaply available, low-toxic, and biodegradable, which makes them predominantly required for large-scale applications effectively in industrial production. Herein we report the [2+3] cycloaddition reaction of organic nitriles with sodium azide affords the corresponding 5-substituted 1H-tetrazoles in six different types of choline chloride based deep eutectic solvents under mild reaction condition. Choline chloride: ZnCl2 (1:2) showed the best results for the synthesis of 5-substituted 1 H-tetrazoles. This method reduces the disadvantages such as: the use of toxic metals and expensive reagents, drastic reaction conditions and the presence of dangerous hydrazoic acid. The approach provides environment-friendly, short reaction times, good to excellent yields; safe process and simple workup make this method an attractive and useful contribution to present green organic synthesis of 5-substituted-1H-tetrazoles. All synthesized compounds were characterized by IR, 1H NMR, 13C NMR and Mass spectroscopy. DES can be recovered and reused three times with very little loss in activity.

Keywords: click chemistry, choline chloride, green chemistry, deep eutectic solvent, tetrazoles

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520 Personalized Email Marketing Strategy: A Reinforcement Learning Approach

Authors: Lei Zhang, Tingting Xu, Jun He, Zhenyu Yan


Email marketing is one of the most important segments of online marketing. It has been proved to be the most effective way to acquire and retain customers. The email content is vital to customers. Different customers may have different familiarity with a product, so a successful marketing strategy must personalize email content based on individual customers’ product affinity. In this study, we build our personalized email marketing strategy with three types of emails: nurture, promotion, and conversion. Each type of email has a different influence on customers. We investigate this difference by analyzing customers’ open rates, click rates and opt-out rates. Feature importance from response models is also analyzed. The goal of the marketing strategy is to improve the click rate on conversion-type emails. To build the personalized strategy, we formulate the problem as a reinforcement learning problem and adopt a Q-learning algorithm with variations. The simulation results show that our model-based strategy outperforms the current marketer’s strategy.

Keywords: email marketing, email content, reinforcement learning, machine learning, Q-learning

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519 Synthesis and Catalytic Activity of N-Heterocyclic Carbene Copper Catalysts Supported on Magnetic Nanoparticles

Authors: Iwona Misztalewska-Turkowicz, Agnieszka Z. Wilczewska, Karolina H. Markiewicz


Carbenes - species which possess neutral carbon atom with two shared and two unshared valence electrons, are known for their high reactivity and instability. Nevertheless, it is also known, that some carbenes i.e. N-heterocyclic carbenes (NHCs), can form stable crystals. The usability of NHCs in organic synthesis was studied. Due to their exceptional properties (high nucleophilicity) NHCs are commonly used as organocatalysts and also as ligands in transition metal complexes. NHC ligands possess better electron-donating properties than phosphines. Moreover, they exhibit lower toxicity. Due to these features, phosphines are frequently replaced by NHC ligands. In this research is discussed the synthesis of five-membered NHCs which are mainly obtained by deprotonation of azolium salts, e.g., imidazolium or imidazolinium salts. Some of them are immobilized on a solid support what leads to formation of heterogeneous, recyclable catalysts. Magnetic nanoparticles (MNPs) are often used as a solid support for catalysts. MNPs can be easily separated from the reaction mixture using an external magnetic field. Due to their low size and high surface to volume ratio, they are a good choice for immobilization of catalysts. Herein is presented synthesis of N-heterocyclic carbene copper complexes directly on the surface of magnetic nanoparticles. Formation of four different catalysts is discussed. They vary in copper oxidation state (Cu(I) and Cu(II)) and structure of NHC ligand. Catalysts were tested in Huisgen reaction, a type of copper catalyzed azide-alkyne cycloaddition (CuAAC) reaction. Huisgen reaction represents one of the few universal and highly efficient reactions in which 1,2,3-triazoles can be obtained. The catalytic activity of all synthesized catalysts was compared with activity of commercially available ones. Different reaction conditions (solvent, temperature, the addition of reductant) and reusability of the obtained catalysts were investigated and are discussed. The project was financially supported by National Science Centre, Poland, grant no. 2016/21/N/ST5/01316. Analyses were performed in Centre of Synthesis and Analyses BioNanoTechno of University of Bialystok. The equipment in the Centre of Synthesis and Analysis BioNanoTechno of University of Bialystok was funded by EU, as a part of the Operational Program Development of Eastern Poland 2007-2013, project: POPW.01.03.00-20-034/09-00 and POPW.01.03.00-20-004/11.

Keywords: N-heterocyclic carbenes, click reaction, magnetic nanoparticles, copper catalysts

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518 Synthesis and Structural Characterization of 6-Nitroindazole Derivatives

Authors: Mohamed El Moctar Abeidi


The indazole derivatives exhibit a wide spectrum of biological activities. They are known for their anti-tumor, antiplatelet, anti-viral, anti-microbial, anti-inflammatory, anti-leishmania and even anti-spermatogen. As part of our research on the synthesis of a number of heterocycles capable of exhibiting a biological and pharmacological property, due to our ongoing interest in the development of a simple and low-cost procedure for obtaining heterocyclic compounds that may have an interest for medicinal purposes. We present in this work the synthesis of 6-nitro-indazoles derivatives, using two different methods. the first method is the alkylation of Nitroindazole by two different alkylating agents under the conditions of solid/liquid phase transfer catalysis in N, N-dimethylformamide (DMF) in the presence of potassium carbonate (K₂CO₃) as a base, and tetra-n-butylammonium bromide (BTBA) as a catalyst. While the other method is the 1,3-dipolar cycloaddition, in this case, we have undertaken the preparation of bi-heterocyclic containing the 6-nitroindazole associate with group of isoxazoline, isoxazole or 1,2,3-Triazole under normal conditions and, under the catalytic conditions of the click chemistry we were also able to determine the structures without any ambiguity by the ¹H and ¹³C NMR.

Keywords: indazole, 6-nitroindazole, isoxazole, 1, 2, 3-Triazole

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517 Virtual Chemistry Laboratory as Pre-Lab Experiences: Stimulating Student's Prediction Skill

Authors: Yenni Kurniawati


Students Prediction Skill in chemistry experiments is an important skill for pre-service chemistry students to stimulate students reflective thinking at each stage of many chemistry experiments, qualitatively and quantitatively. A Virtual Chemistry Laboratory was designed to give students opportunities and times to practicing many kinds of chemistry experiments repeatedly, everywhere and anytime, before they do a real experiment. The Virtual Chemistry Laboratory content was constructed using the Model of Educational Reconstruction and developed to enhance students ability to predicted the experiment results and analyzed the cause of error, calculating the accuracy and precision with carefully in using chemicals. This research showed students changing in making a decision and extremely beware with accuracy, but still had a low concern in precision. It enhancing students level of reflective thinking skill related to their prediction skill 1 until 2 stage in average. Most of them could predict the characteristics of the product in experiment, and even the result will going to be an error. In addition, they take experiments more seriously and curiously about the experiment results. This study recommends for a different subject matter to provide more opportunities for students to learn about other kinds of chemistry experiments design.

Keywords: virtual chemistry laboratory, chemistry experiments, prediction skill, pre-lab experiences

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516 Testing the Readiness of Chemistry Teachers for the Use of Information and Communication Technologies in Teaching Chemistry

Authors: Nikolina Ribarić


This paper compares the readiness of chemistry teachers to use information and communication technologies in chemistry in 2018. and 2021. A survey conducted in 2018. on a sample of teachers showed that most teachers occasionally use visualization and digitization tools in chemistry teaching (65%), but feel that they are not educated enough to use them (56%). Also, most teachers do not have adequate equipment in their schools and are not able to use ICT in teaching or digital tools for visualization and digitization of content (44%). None of the teachers find the use of digitization and visualization tools useless. Furthermore, a survey conducted in 2021. shows that most teachers occasionally use visualization and digitization tools in chemistry teaching (83%). Also, the research shows that some teachers still do not have adequate equipment in their schools and are not able to use ICT in chemistry teaching or digital tools for visualization and digitization of content (14%). Advances in the use of ICT in chemistry teaching are linked to pandemic conditions and the obligation to conduct online teaching. The share of 14% of teachers who still do not have adequate equipment to use digital tools in teaching is worrying.

Keywords: chemistry, digital content, e-learning, ICT, visualization

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515 Multi-Stream Graph Attention Network for Recommendation with Knowledge Graph

Authors: Zhifei Hu, Feng Xia


In recent years, Graph neural network has been widely used in knowledge graph recommendation. The existing recommendation methods based on graph neural network extract information from knowledge graph through entity and relation, which may not be efficient in the way of information extraction. In order to better propose useful entity information for the current recommendation task in the knowledge graph, we propose an end-to-end Neural network Model based on multi-stream graph attentional Mechanism (MSGAT), which can effectively integrate the knowledge graph into the recommendation system by evaluating the importance of entities from both users and items. Specifically, we use the attention mechanism from the user's perspective to distil the domain nodes information of the predicted item in the knowledge graph, to enhance the user's information on items, and generate the feature representation of the predicted item. Due to user history, click items can reflect the user's interest distribution, we propose a multi-stream attention mechanism, based on the user's preference for entities and relationships, and the similarity between items to be predicted and entities, aggregate user history click item's neighborhood entity information in the knowledge graph and generate the user's feature representation. We evaluate our model on three real recommendation datasets: Movielens-1M (ML-1M), LFM-1B 2015 (LFM-1B), and Amazon-Book (AZ-book). Experimental results show that compared with the most advanced models, our proposed model can better capture the entity information in the knowledge graph, which proves the validity and accuracy of the model.

Keywords: graph attention network, knowledge graph, recommendation, information propagation

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514 Evaluation of Commercial Herbicides for Weed Control and Yield under Direct Dry Seeded Rice Cultivation System in Pakistan

Authors: Sanaullah Jalil, Abid Majeed, Syed Haider Abbas


Direct dry seeded rice cultivation system is an emerging production technology in Pakistan. Weeds are a major constraint to the success of direct dry seeded rice (DDSR). Studies were carried out for two years during 2015 and 2016 to evaluate the performance of applications of pre-emergence herbicides (Top Max @ 2.25 lit/ha, Click @1.5 lit/ha and Pendimethaline @ 1.25 lit/ha) and post-emergence herbicides (Clover @ 200 g/ha, Pyranex Gold @ 250 g/ha, Basagran @ 2.50 lit/ha, Sunstar Gold @ 50 g/ha and Wardan @ 1.25 lit/ha) at rice research field area of National Agriculture Research Center (NARC), Islamabad. The experiments were laid out in Randomized Complete Block Design (RCBD) with three replications. All evaluated herbicides reduced weed density and biomass by a significant amount. The net plot size was 2.5 x 5 m with 10 rows. Basmati-385 was used as test variety of rice. Data indicated that Top Max and Click provided best weed control efficiency but suppressed the germination of rice seed which causes the lowest grain yield production (680.6 kg/ha and 314.5 kg/ha respectively). A weedy check plot contributed 524.7 kg/ha paddy yield with highest weed density. Pyranex Gold provided better weed control efficiency and contributed to significantly higher paddy yield 5116.6 kg/ha than that of all other herbicide applications followed by the Clover which give paddy yield 4241.7 kg/ha. The results of our study suggest that pre-emergence herbicides provided best weed control but not fit for direct dry seeded rice (DDSR) cultivation system, and therefore post-emergence herbicides (Pyranex Gold and Clover) can be suggested for weed control and higher yield.

Keywords: pyranex gold, clover, direct dry seeded rice (DDSR), yield

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513 Evaluating the Prominence of Chemical Phenomena in Chemistry Courses

Authors: Vanessa R. Ralph, Leah J. Scharlott, Megan Y. Deshaye, Ryan L. Stowe


Given the traditions of chemistry teaching, one may not question whether chemical phenomena play a prominent role. Yet, the role of chemical phenomena in an introductory chemistry course may define the extent to which the course is introductory, chemistry, and equitable. Picture, for example, the classic Ideal Gas Law problem. If one envisions a prompt wherein students are tasked with calculating a missing variable, then one envisions a prompt that relies on chemical phenomena as a context rather than as a model to understand the natural world. Consider a prompt wherein students are tasked with applying molecular models of gases to explain why the vapor pressure of a gaseous solution of water differs from that of carbon dioxide. Here, the chemical phenomenon is not only the context but also the subject of the prompt. Deliveries of general and organic chemistry were identified as ranging wildly in the integration of chemical phenomena. The more incorporated the phenomena, the more equitable the assessment task was for students of varying access to pre-college math and science preparation. How chemical phenomena are integrated may very well define whether courses are chemistry, are introductory, and are equitable. Educators of chemistry are invited colleagues to discuss the role of chemical phenomena in their courses and consider the long-lasting impacts of replicating tradition for tradition’s sake.

Keywords: equitable educational practices, chemistry curriculum, content organization, assessment design

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512 Comparison of Mcgrath, Pentax, and Macintosh Laryngoscope in Normal and Cervical Immobilized Manikin by Novices

Authors: Jong Yeop Kim, In Kyong Yi, Hyun Jeong Kwak, Sook Young Lee, Sung Yong Park


Background: Several video laryngoscopes (VLs) were used to facilitate tracheal intubation in the normal and potentially difficult airway, especially by novice personnel. The aim of this study was to compare tracheal intubation performance regarding the time to intubation, glottic view, difficulty, and dental click, by a novice using McGrath VL, Pentax Airway Scope (AWS) and Macintosh laryngoscope in normal and cervical immobilized manikin models. Methods: Thirty-five anesthesia nurses without previous intubation experience were recruited. The participants performed endotracheal intubation in a manikin model at two simulated neck positions (normal and fixed neck via cervical immobilization), using three different devices (McGrath VL, Pentax AWS, and Macintosh direct laryngoscope) at three times each. Performance parameters included intubation time, success rate of intubation, Cormack Lehane laryngoscope grading, dental click, and subjective difficulty score. Results: Intubation time and success rate at the first attempt were not significantly different between the 3 groups in normal airway manikin. In the cervical immobilized manikin, the intubation time was shorter (p = 0.012) and the success rate with the first attempt was significantly higher (p < 0.001) when using McGrath VL and Pentax AWS compared with Macintosh laryngoscope. Both VLs showed less difficulty score (p < 0.001) and more Cormack Lehane grade I (p < 0.001). The incidence of dental clicks was higher with McGrath VL than Macintosh laryngoscope in the normal and cervical immobilized airway (p = 0.005, p < 0.001, respectively). Conclusion: McGrath VL and Pentax AWS resulted in shorter intubation time, higher first attempt success rate, compared with Macintosh laryngoscope by a novice intubator in a cervical immobilized manikin model. McGrath VL could be reduced the risk of dental injury compared with Macintosh laryngoscope in this scenario.

Keywords: intubation, manikin, novice, videolaryngoscope

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511 Professional Ambitions of Students of Faculty of Chemistry, Adam Mickiewicz University in the Context of Teaching Profession

Authors: Malgorzata Bartoszewicz, Grzegorz Krzysko


Chemistry students plan a career path based on their interests, predispositions, and preferences. This study aims to determine what percentage of all chemistry students selected teaching as a career. There is a lack of science teachers (especially physics and chemistry) in Poland, and there is limited research on students' choices and professional preferences. At the Faculty of Chemistry of the Adam Mickiewicz University in the academic year 2019/2020, changes were introduced to the study program resulting from legal regulations and as part of the funds raised from the project "Teacher - competent practitioner, supervisor, expert", No. POWR.03.01.00-00-KN40/18. The aim of the study was to determine how many first-cycle and second-cycle studies students declare the teaching profession as a career. In the case of first-cycle studies students, 9.5% of respondents choose the teaching profession and 9.2% of second-cycle studies students. It was found that the number of students who chose the teacher preparation programme at Faculty of Chemistry of the Adam Mickiewicz University has decreased since 5 years.

Keywords: faculty of chemistry, Adam Mickiewicz University, professional ambitions, students, teacher

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510 Implementation of an Undergraduate Integrated Biology and Chemistry Course

Authors: Jayson G. Balansag


An integrated biology and chemistry (iBC) course for freshmen college students was developed in University of Delaware. This course will prepare students to (1) become interdisciplinary thinkers in the field of biology and (2) collaboratively work with others from multiple disciplines in the future. This paper documents and describes the implementation of the course. The information gathered from reading literature, classroom observations, and interviews were used to carry out the purpose of this paper. The major goal of the iBC course is to align the concepts between Biology and Chemistry, so that students can draw science concepts from both disciplines which they can apply in their interdisciplinary researches. This course is offered every fall and spring semesters of each school year. Students enrolled in Biology are also enrolled in Chemistry during the same semester. The iBC is composed of lectures, laboratories, studio sessions, and workshops and is taught by the faculty from the biology and chemistry departments. In addition, the preceptors, graduate teaching assistants, and studio fellows facilitate the laboratory and studio sessions. These roles are interdependent with each other. The iBC can be used as a model for higher education institutions who wish to implement an integrated biology course.

Keywords: integrated biology and chemistry, integration, interdisciplinary research, new biology, undergraduate science education

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509 Synthesis of 5'-Azidonucleosides as Building Blocks for the Preparation of Biologically Active Bioconjugates

Authors: Brigitta Bodnár, Lajos Kovács, Zoltán Kupihár


The cancer cells require higher amount of nucleoside building blocks for their proliferation, therefore they have significantly higher uptake of nucleosides by the different nucleoside transporters. Therefore, the conjugation with nucleosides may significantly increase the efficiency and selectivity of potential active pharmaceutical ingredients. On the other hand, the advantage of using a nucleoside could be either the higher activity on targeted enzymes overrepresented in cancer cells or an enhanced cellular uptake of the bioconjugates in these cells compared to the healthy ones. This fact can be used to make the nucleosides, as targeting moieties covalently bound to anti-cancer drug molecules which can selectively accumulate in cancer cells. However, in order to form the nucleoside-drug conjugates, such nucleoside building blocks are needed, which can selectively be coupled to the drug molecules containing even a high number of diverse functional groups. One of the most selective conjugation techniques is the copper-catalyzed azide-alkyne click reaction that requires the presence of an alkyl group on one of the conjugated molecules and an azide group on the other. In case of nucleosides, the development of azide group is simpler for which the replacement of the 5'-hydroxy group is the most suitable. This transformation generally involves many side reactions and result in very low yields. In addition, during our experiments, the transformation of the 2'-deoxyguanosine to the corresponding 5'-deoxy-5’-azido-2’-deoxyguanosine could not be performed with any of the methods described in the literature. Therefore, we have tried to overcome these difficulties with not only using the traditional process based on the 2 step exchange of tosyl to azide, but also using the Mitsunobu reaction which requires only one step. However, this path proved to be unsuccessful in spite of the optimizing the reaction conditions. Finally, a method has been developed whereby the azide groups were incorporated into the 5’-position resulting in significantly better yields compared to all other previous methods, and we were able to produce all the four nucleoside derivatives.

Keywords: 5'-azidonucleosides, bioconjugate, click reaction, proliferation

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508 Small-Group Case-Based Teaching: Effects on Student Achievement, Critical Thinking, and Attitude toward Chemistry

Authors: Reynante E. Autida, Maria Ana T. Quimbo


The chemistry education curriculum provides an excellent avenue where students learn the principles and concepts in chemistry and at the same time, as a central science, better understand related fields. However, the teaching approach used by teachers affects student learning. Cased-based teaching (CBT) is one of the various forms of inductive method. The teacher starts with specifics then proceeds to the general principles. The students’ role in inductive learning shifts from being passive in the traditional approach to being active in learning. In this paper, the effects of Small-Group Case-Based Teaching (SGCBT) on college chemistry students’ achievement, critical thinking, and attitude toward chemistry including the relationships between each of these variables were determined. A quasi-experimental counterbalanced design with pre-post control group was used to determine the effects of SGCBT on Engineering students of four intact classes (two treatment groups and two control groups) in one of the State Universities in Mindanao. The independent variables are the type of teaching approach (SGCBT versus pure lecture-discussion teaching or PLDT) while the dependent variables are chemistry achievement (exam scores) and scores in critical thinking and chemistry attitude. Both Analysis of Covariance (ANCOVA) and t-tests (within and between groups and gain scores) were used to compare the effects of SGCBT versus PLDT on students’ chemistry achievement, critical thinking, and attitude toward chemistry, while Pearson product-moment correlation coefficients were calculated to determine the relationships between each of the variables. Results show that the use of SGCBT fosters positive attitude toward chemistry and provides some indications as well on improved chemistry achievement of students compared with PLDT. Meanwhile, the effects of PLDT and SGCBT on critical thinking are comparable. Furthermore, correlational analysis and focus group interviews indicate that the use of SGCBT not only supports development of positive attitude towards chemistry but also improves chemistry achievement of students. Implications are provided in view of the recent findings on SGCBT and topics for further research are presented as well.

Keywords: case-based teaching, small-group learning, chemistry cases, chemistry achievement, critical thinking, chemistry attitude

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