Chemistry Commons^™

Cloud Point Extraction In Conjunction With Tangential Flow Filtration (Cpe-Tff) For The Enhanced Separation Of Silver Nanoparticles And Silver Ions From Aqueous Colloids And Biological Matrices, Md Ali Akbar

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The extensive use of silver nanoparticles (AgNPs) in consumer products and research is accompanied by their inevitable release into the environment. While the environmental fate of AgNPs is still under investigation, most in vitro and in vivo studies agree that the main toxicity of AgNPs is directly related to the release of Ag+ ions from AgNPs. In this study, cloud point extraction (CPE) was combined with tangential flow filtration (TFF) for the enhanced separation of AgNPs and Ag+ from aqueous colloids and biological matrices. The feasibility of the CPE-TFF method was demonstrated on four colloidal (borohydride-, PVP-, citrate-capped and uncapped …

Green Chemistry: Progress And Barriers, Sarah A. Green

Michigan Tech Publications, Part 1

Green chemistry can advance both the health of the environment and the primary objectives of the chemical enterprise: to understand the behavior of chemical substances and to use that knowledge to make useful substances. We expect chemical research and manufacturing to be done in a manner that preserves the health and safety of workers; green chemistry extends that expectation to encompass the health and safety of the planet. While green chemistry may currently be treated as an independent branch of research, it should, like safety, eventually become integral to all chemistry activities. While enormous progress has been made in shifting …

Bioavailability And Transformation Of Silver Nanoparticles In The Freshwater Environment, Seth W. Brittle

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The proliferation of silver nanoparticles (AgNPs) in consumer products and industrial applications has generated many environmental concerns since the chemistry of silver changes at the nanoscale and the very properties that make them desirable – their unique reactivity – may pose environmental risks. This dissertation addresses these concerns from three different angles. First, freshwater crayfish is demonstrated as a potential benthic indicator of Ag pollution since Ag accumulation depends on the form of Ag. The uptake and distribution of Ag (from AgNPs or Ag+) in tissue samples were measured by inductively coupled plasma optical emission spectroscopy (ICP-OES). The hepatopancreas (1.5-17.4 …

Synthesis, Characterization, And Polymerization Of Sulfonamide Based Bifunctional Monomers, Brady Hall

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A series of bifunctional monomers based on N,N-diallylbenzenesulfonamides with varying groups on the benzene moiety were investigated. The main goal of this project was to polymerize these monomers using radical and acyclic diene metathesis (ADMET) polymerization methods to polymerize through the allyl groups, and nucleophilic aromatic substitution (SNAr) to polymerize through the fluorine groups on the phenyl ring. Using phenyl substituted benzenesulfonyl chloride derivatives as a starting material, a series of N,N-diallylbenzenesulfonamide derivatives were prepared. The ADMET and radical cyclopolymerizations were monitored by 1H NMR spectroscopy, observing the disappearance of signals for the allyl groups in both, and the appearance …

Synthesis And Characterization Of Functionalized Poly(Arylene Ether Sulfone)S Using Click Chemistry, Kavitha Neithikunta

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Poly(arylene ether sulfone)s with pendent aryl iodide group was successfully synthesized via Nucleophilic aromatic polycondensation of 1-(3,5-difluorophenyl sulfonyl)-4-iodobenzene using 4,4’-difluorodiphenylsulfone (DFDPS) and Bisphenol A in the ratio 25:75:100. Iodo monomer was prepared by reacting 3,5-difluorodiphenyl sulfone with N-iodo succinimide (NIS). Using GC/MS and NMR spectroscopy, the quantitative analysis was done to this monomer. Modification was done to iodo copolymer using sodium azide and copper sulfate as catalyst to form azide copolymer. Further modification of the azide copolymer to triazole copolymers via Click Chemistry using different alkynes such as 1-octyne, phenyl acetylene, propargyl alcohol and acetylenedicarboxylic acid. Polymers characterization was done …

An Investigation Of The Adsorption Behavior Between Silver Nanoparticles (Agnps) And Corundum (Α-Al2O3) At Environmental Ph Values Using Inductively-Coupled Plasma Optical Emission Spectroscopy (Icp-Oes) And Raman Spectroscopy, Kevin Andrew O'Neil

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With the increased use of silver nanoparticles (AgNPs) in consumer products, the need to monitor their release into environmental soils has become critical. Although minerals make up a large component of soils, research on their interactions with AgNPs is still limited. Furthermore, the majority of the existing research focused on silica-based minerals rather than metal oxides, which is the second most abundant mineral type in the earth's crust. This study examined for the first time the aqueous interaction between the widely used, spherical Creighton AgNPs and a-corundum (a-Al2O3), a representative non-silica-based mineral, at environmentally relevant pH values (6-11). Samples were …

Theoretical Estimation Of PkA'S Of Pyrimidines And Related Heterocycles, Rachael Ann Wessner

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Pyrimidines and related heterocycles are an important class of compounds with a wide variety of applications. As a result, there is great interest in the chemical properties of these compounds, specifically their pKa's. Despite the importance of these compounds their reported pKa's are often only approximations or are completely absent from literature. Experimentally measuring pKa's can be challenging, especially if the pKa is below zero. Alternatively, pKa's can be estimated computationally using a Quantitative Structure-Activity Relationship (QSAR). However, most of the compounds included in this study exist as two or more forms that arise from tautomerism. Tautomerism complicates the estimation …

Design And Application Of Facile Routes To N-Heterocycle Functionalized Poly(Arylene Ether)S, Abraham K. Kemboi

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A series of 3,5-difluorinated systems, which are activated towards nucleophilic aromatic substitution (NAS) by the strongly electron withdrawing benzoxazole or benzothiazole groups, located meta to the fluorines were prepared and fully characterized. The monomers also carry various N-heterocyclic species on the non-fluorinated ring. The corresponding poly(arylene ether)s, some of which were copolymers with triphenylphosphine oxide-based monomers, were prepared via standard NAS polycondensation reactions. Incorporation of the monomers containing N-heterocycle units was determined by NMR spectroscopy. Characterization of the thermal properties was done using thermogravimetric analysis (TGA) and differential scanning (DSC). Most of the polymers displayed good film forming properties when …

Synthesis And Characterization Of Peek Analogues Utilizing 3,5- And 2,4-Difluorobenzophenone., Zachary Ewing

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Two routes to semi-crystalline, potentially functionalizable poly(ether ether ketone), PEEK, analogues were explored using varying percentages of 4,4’-difluorobenzophenone and either 3,5-difluorobenzophenone or 2,4-difluorobenzophenone as the electrophilic component in nucleophilic aromatic substitution polycondensation reactions with hydroquinone. PEEK analogues utilizing 3,5-difluorobenzophenone were carried out in a “one-pot” fashion and their properties were compared to the same materials prepared previously by a multi-step synthetic procedure. The use of 2,4-difluorobenzophenone led to completely new PEEK analogues. The polymers were characterized via NMR spectroscopy, Size Exclusion Chromatography, Thermogravimetic Analysis, and Differential Scanning Calorimetry. Molecular weight determinations showed the synthesized polymers to be of a variety …

Alkylenedioxy Containing Peek Polymers Containing Meta Linkages, James Uchenna Ohaeri

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The oxyalkylene containing, meta linked monomers 1,2-bis(3-(4-fluorobenzoyl)phenoxy)ethane, 1,3-bis(3-(4-fluorobenzoyl)phenoxy)propane, 1,4-bis(3-(4-fluorobenzoyl)phenoxy)butane, 1,5-bis(3-(4-fluorobenzoyl)phenoxy)pentane can be prepared by a three-step process starting with the dialdehydes (1,2-bis(3-formylphenoxy)ethane, 1,3-bis(3-formylphenoxy)propane, 1,4-bis(3-formylphenoxy)butane and 1,5-bis(3-formylphenoxy)pentane, respectively). Polymerization of the monomers with bisphenol-A gave soluble, thermally stable amorphous poly(ether ether ketone)s. The polymers exhibited molecular weights of (Mw/Mn) (21,841/ 8721) g/mol, (21,195/ 7569) g/mol, (9,107/ 2819) g/mol and (12,990/ 4723) g/mol, respectively. Thermal analyses of the polymers revealed Tgs of 112º, 106º, 92º and 91º, respectively and 5% weight losses under a nitrogen atmosphere of 389º, 410º, 411º and 414º, respectively.

Routes To 1,3,4 - Oxadiazol-2(3h)-Ones, Karunakar Reddy Madaram

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Various 1,3,4-oxadiazol-2(3H)-ones were synthesized by reaction of the bromocarbonylhydrazine salt(35) obtained from treatment of 4-bromo-3-phenylsydnone(34) with HCl with the corresponding acid chlorides in DME. The structures were confirmed by their physical, analytical and spectral data (IR, GC/MS, 1H and 13C NMR and CHN analysis). In general these compounds were synthesized in good to excellent yields and it is planned to continue exploration of their chemical behavior as a guide to their potential antimicrobial activity. As an initial approach to the synthesis of the desired 1,3,4-oxadiazol-2(3H)-ones, the starting material, 3-phenylsydnone, was prepared in 2 steps from commercially available N-phenylglycine in good …

Determination Of Atmospheric Particulate Matter Composition In The Dayton Metro Area, Saagar Mahendra Patel

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Quartz filters from high-volume air samplers of particulate matter of a size less than 10 micrometers in diameter (PM₁₀) located in Moraine and Yellow Springs, Ohio, were obtained from the Regional Air Pollution Control Agency and analyzed for levoglucosan, metals, and the EPA 16 priority polycyclic aromatic hydrocarbons (PAHs). Average concentration of levoglucosan increased as ambient temperature decreased. Winter concentrations of levoglucosan for Moraine and Yellow Springs were 39.41 ± 31.58 µg/g and 51.52 ± 27.44 µg/g, respectively, which is due to a greater amount of residential wood burning in the colder months. The concentration of biomass burning …

Poly(Arylene Ether Sulfone)S With Ammonium Groups Located On Pendent Phenyl Sulfonyl Moieties For Anionic Exchange Membranes, Trevor I. Schumacher

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A series of poly(aryl ether sulfone)s with varying percentages of ammonium groups, located on truly pendent positions, was prepared and characterized. The initial polymers were prepared by nucleophilic aromatic substitution (NAS) polycondensation reactions of varying ratios of 3,5-difluoro-4'-methyldiphenylsulfone and 4,4'-difluorodiphenylsulfone, with bisphenol-A as the nucleophilic reaction partner. The tolyl groups in the resulting polymers were subjected to radical bromination with N-bromosuccinimide, followed by amination with three different amines: trimethylamine, dimethylhexadecylamine, and N-methylimidazole. The polymers were characterized by 1H and 13C NMR spectroscopy, thermogravimetric analysis, and differential scanning calorimetry. With the exception of the 100% functionalized polymers, tough films were observed …

Vespucci: A Free, Cross-Platform Software Tool For Spectroscopic Data Analysis And Imaging, Daniel Patrick Foose

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Vespucci is a software application developed for imaging and analysis of hyperspectral datasets. Vespucci offers several advantages over other software packages, including a simple user interface, no cost, and less restrictive licensing. Vespucci incorporates several analysis techniques including univariate imaging, principal components analysis, partial-least-squares regression, vertex components analysis and k- means clustering. Additionally, Vespucci can perform a number of useful data-processing operations, including filtering, normalization, baseline correction, and background subtraction. Datasets that consist of spatial or temporal data with a corresponding digital signal, including spectroscopic images, mass spectrometric images, and X-ray diffraction data can be processed in this software. The …

Thermal Properties Of Poly(Arylene Ether)S Prepared From N,N-Dialkyl-2,4-Difluorobenzenesulfonamides, James Kanyoko Waweru

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A series of poly(arylene ether)s were synthesized by nucleophilic aromatic substitution reaction (NAS) polycondensation of N,N-dialkyl-2,4-difluorobenzenesulfonamides. The aim of the project was to determine the thermal properties of poly(arylene ether)s by varying pendent sulfonamide activating group. The sulfonamide-activated monomers were synthesized by reacting 2,4-difluorobenzenesulfonyl chloride with a series of n-alkyl, iso-alkyl and cycloalkyl amines, ranging from n-propyl to n-octyl. Their poly(arylene ether)s were prepared with bisphenol-A as the nucleophilic reaction partner. The 4’-bromo-2,4-difluorodiphenylsulfone monomer, was utilized to synthesized copolymer with 4,4’-difluorodiphenylsulfone and bisphenol-A. The polymers were characterized by 1H and 13C NMR spectroscopy, TGA, DSC and SEC. Sulfonamide based polymers, …

Data In Support Of Quantification Of Pyrophosphate As A Universal Approach To Determine Polymerase Activity And Assay Polymerase Inhibitors, S. Malvezzi, S. J. Sturla, Marina Tanasova

Michigan Tech Publications, Part 1

Characterization of synthetic oligonucleotides and quantification of primer extension mediated by a human translesion synthesis polymerase η (Pol η) over drug-induced DNA lesions in the presence on modified nucleotide analogs is described. Extent of primer extension for each reaction was monitored by denaturing gel electrophoresis. The data was obtained to assess the performance of the fluorescence-based primer extension (PE-PiPer) assay [1] with respect to the established and conventionally used denaturing gel electrophoresis. The obtained data reflects the specific inhibition of translesion synthesis over cisplatin containing DNA with 5-OH-CTP.

Extracellular Expression Of Alkaline Phytase In Pichia Pastoris: Influence Of Signal Peptides, Promoters And Growth Medium, Mimi Yang, Sasha Teymorian, Philip Olivares, Pushpalatha P.N. Murthy

Michigan Tech Publications, Part 1

Alkaline phytase isolated from pollen grains of Lilium longiflorum (LlALP) possesses unique catalytic and thermal stability properties that suggest it has the potential to be used as a feed supplement. However, substantial amounts of active enzymes are needed for animal feed studies and endogenous levels of LlALP in lily pollen are too low to provide the required amounts. Active rLlALP2 (coded by LlAlp2, one of two isoforms of alkaline phytase cDNA identified in lily pollen) has been successfully expressed in intracellular compartments of Pichia pastoris, however enzyme yields have been modest (25-30 mg/L) and purification of the enzyme has been …

Proxy-Pet Building Blocks As A Design Element For Library Synthesis, Lainey Jo Mallin

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In exploring radioligands for positron emission tomography (PET) imaging, it is not unusual to synthesize a library of compounds around some targeting scaffold, screen for optimal binding to a relevant diagnostic cellular target, remove some portion of optimized molecule so as to append the requisite reporter group, and then re-evaluate. To this end, the use of "click labeling" in radiochemistry is proving an increasingly attractive means of conjugating a 18F-reporter group, wherein the targeting scaffold bearing a terminal alkyne is allowed to react with a 2-[18F]-fluoroethylazide to forge a linkage as a 1,2,3-triazole substituent. Since the triazole linked prosthetic group …

Computational Estimation Of The Pka's Of Purines And Related Compounds, Kara L. Geremia

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The acid dissociation value pKa of a compound provides important information regarding the neutral and ionic forms of the compound present under different conditions. However, for many compounds experimental pKa values are not available, and for others the measured values are sometimes uncertain. Consequently, having a computational means for estimating pKa values can be of benefit for biochemical, pharmaceutical, polymer, and many other studies. Purines form a key group of bioactive compounds whose acid/base activities are of considerable interest. The purine class includes such diverse compounds as the nucleic acid bases adenine and guanine, the gout-related compound uric acid, the …

Investigation Of Solvent-Dependent Properties Of Donor And Acceptor Materials For Photovoltaic Applications, Anna L. Foote

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The choice of solvent and additive has been shown to affect efficiency of organic solar cell devices. To gain a basic understanding of the role of solvents in influencing overall device performance, we present a comparative study on the physical properties of donor: acceptor mixtures in different solvents. Investigations have been carried out for P3HT (poly(3-hexylthiophene-2,5-diyl)), PTB7 (poly[4,8-bis[(2-ethylhexyl)oxy]benzo[1,2-b:4,5-b']-dithiophene-2,6-diyl][3-fluro-2-[2-ethylhexyl)carbonyl[thieno[3,4-b]thiophenediyl]]), PC61BM ([6,6]-phenyl-C60-butyric acid methyl ester), and PC71BM ([6,6]-phenyl-C70-butyric acid methyl ester). The physical properties reported are based on UV-Vis absorption spectroscopy, resistance measurements, cyclic voltammetry measurements, and surface energy characterizations of the organic films. The solvents used to prepare the organic films …

Tuning The Physical Properties Of Poly(Arylene Ether)S Prepared From 3,5-Difluorobenzene Sulfonamides, Renata Mitton

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A series of functionalized poly(arylene ether)s, PAEs, based on 3,5-difluorobenzene sulfonamides with varying groups on the sulfonamide moiety were investigated. The main goal of the project was to tune the physical properties of the PAEs by altering the organic groups present on the sulfonamide nitrogen atom, including combinations of aryl iodide, alkyl, allyl, 4-ethoxycarboxylphenyl and benzyl moieties.

Using 3,5-difluorobenzenesulfonyl chloride as a starting material, N-R1-N-R2-3,5-difluorobenzenesulfonamides were prepared, followed by conversion to the corresponding PAEs by reaction of 3,5-difluorobenzene sulfonamides with Bisphenol-A, via a typical NAS polycondensation. Copolymers with varying contents of the functional monomer ranging from 10 to 25 %, …

Work Function Modification Of Metal Electrodes Via Printing Of Pedot:Pss And Carbon Nanotubes, Carly A. Jordan

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Work function tunability of metal electrodes provides a route to improving performance of organic electronic devices. Using an electrode with a different work function changes the potential barrier at the polymer/electrode interface, leading to altered device characteristics, such as turn-on voltage in light emitting diodes or series resistance photodiodes. In this work, we explore work function modification by employing solution-based conducting materials, poly(3,4-ethylenedioxythiophene) : poly(styrene sulfonate) (PEDOT:PSS) and carbon nanotubes (CNTs), printed as overcoatings on oxidized Ni. The capability of direct write technologies, namely inkjet and aerosol jet printing, to control thin film thickness is investigated. The correlation between film …

Polymerization Of Peek Ab Monomers With Oxyalkylene Linkages Via Nas And Friedel-Crafts Reactions, Shannon Theresa Hennelly

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The synthesis of the NAS monomer, 4-fluoro-4'-(2-(4-benzyloxyphenoxy)ethoxy) benzophenone, was envisioned as a two-step process. Thus, the synthesis of 4-fluoro- 4'-(2-(4-benzyloxyphenoxy)ethoxy)benzophenone was accomplished by the reaction of 4-fluoro-4'-hydroxybenzophenone and 1-(benzyloxy)-4-(2bromoethoxy) benzene. Hydrogenation of 4-fluoro-4'-(2-(4-benzyloxyphenoxy)ethoxy) benzophenone with 10% Pd/C was used to successfully remove the benzylic ether protective group, however, the reaction also reduced the benzophenone carbonyl. The synthesis of the EAS monomer, 4-(2-(4-phenoxyphenoxy)ethoxy)benzoic acid, was also a two-step process. The reaction of ethyl p-(2-hydroxyethoxy)benzoate and 4-phenoxyphenol gave ethyl 4-(2-(4-phenoxyphenoxy)ethoxy)benzoate in good yield. This ester could be easily hydrolyzed to 4-(2-(4-pheonxyphenoxy)ethoxybenzoic acid. The polymerization of the EAS monomer, 4-(2-(4-pheonxyphenoxy)ethoxybenzoic acid, was carried …

Potential Tau Directed Imaging Agents, Amanda Merrill Boyer

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Given the ambident reactivity of oxindoles in terms of N- versus C-alkylation, realization of the three points of diversity available to (presumably benzenoid substituted) benzylidene oxindoles is normally achieved via a sequence involving initial N-alkylation of the corresponding isatin precursor, reductive deoxygenation to the N-alkylated oxindole, and finally aldol condensation to the desired target. Since benzenoid substituted isatins are generally more readily available than the corresponding oxindoles, an alternate but much less examined manifold involves reduction of the isatin to an oxindole, aldolization at the C-3 position followed by N-alkylation of the resultant benzylidene oxindole. Since benzylidene oxindoles have potential …

Modification Of A Single-Molecule Afm Probe With Highly Defined Surface Functionality, Fei Long, Bin Cao, Ashok Khanal, Shiyue Fang, Reza Shahbazian-Yassar

Michigan Tech Publications

Single-molecule force spectroscopy with an atomic force microscope has been widely used to study inter- and intramolecular interactions. To obtain data consistent with single molecular events, a well-defined method is critical to limit the number of molecules at the apex of an AFM probe to one or to a few. In this paper, we demonstrate an easy method for single-molecule probe modification by using the Cu-catalyzed alkyne–azide cycloaddition reaction. Excess terminal alkynes were covalently attached to the probe, and a bi-functional molecule containing an azide at one end and a carboxylic acid at the other was dissolved in the reaction …

Atmospheric Peroxyacetyl Nitrate (Pan): A Global Budget And Source Attribution, E. V. Fischer, D. J. Jacob, R. M. Yantosca, M. P. Sulprizio, D. B. Millet, J. Mao, F. Paulot, H. B. Singh, A. Roiger, L. Ries, R. W. Talbot, K. Dzepina, S. Pandey Deolal

Michigan Tech Publications, Part 1

Peroxyacetyl nitrate (PAN) formed in the atmospheric oxidation of non-methane volatile organic compounds (NMVOCs) is the principal tropospheric reservoir for nitrogen oxide radicals (NOx =NO+NO2). PAN enables the transport and release of NOx to the remote troposphere with major implications for the global distributions of ozone and OH, the main tropospheric oxidants. Simulation of PAN is a challenge for global models because of the dependence of PAN on vertical transport as well as complex and uncertain NMVOC sources and chemistry. Here we use an improved representation of NMVOCs in a global 3-D chemical transport model (GEOS-Chem) and show that it …

A Semi-Lagrangian View Of Ozone Production Tendency In North American Outflow In The Summers Of 2009 And 2010, B. Zhang, R. C. Owen, J A Perlinger, A. Kumar, S. Wu, M. Val Martin, L. Kramer, D. Helmig, R. E. Honrath

Michigan Tech Publications, Part 1

The Pico Mountain Observatory, located at 2225 m a.s.l. in the Azores Islands, was established in 2001 to observe long-range transport from North America to the central North Atlantic. In previous research conducted at the observatory, ozone enhancement (> 55 ppbv) in North American outflows was observed, and efficient ozone production in these outflows was postulated. This study is focused on determining the causes for high d[O3] / d[CO] values (~1 ppbv ppbv−1) observed in the summers of 2009 and 2010. The folded retroplume technique, developed by Owen and Honrath (2009), was applied to combine upwind FLEXPART transport …

Synthesis And Biological Activity Of Indolinones, Kaleb Woodrow Cox

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Indolinones of the type known as Arylidene oxindoles have been demonstrated to possess a broad range of activity ranging from proten kinase inhibtors, cell-death inhibitors and tau protein binding agents. Small libraries of such molecules were designed and synthesized herein in modifications involving variously substituted halogen derivatives, N-alkylation of the indolinone nitrogen, and finally a new class of molecules, namely arylidene oxindoles possessing extended conjugation. The biological activities of such molecules were examined and the results disclosed herein.

The Synthesis Of Benzyloxy Substituted Dp-Ppv And Examination Of The Horner-Wadsworth-Emmons Reaction In The Synthesis Of Dp-Ppv, Jeremy M. Lear

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In the interest of the synthesis of polymers that have the potential to possess inherent light-emitting properties (LEDs) the synthesis of a novel 1,4-bis(chloromethyl)-benzene monomer, 5-benzyloxy-1,4-dichloromethyl-2,3-diphenyl benzene 78 was carried out. Monomer 78 was polymerized via the Gilch polymerization method to yield, poly(5-benzyloxy-2,3-diphenyl phenylene vinylene) 80. Polymer 80 was characterized by TGA (5% weight loss at 267°, GPC (weight average molecular weight of 7136 Da, number average molecular weight of 6603 Da) , UV-Vis and fluorescence studies (absorbance maximum at 406 nm, emission maximum at 510 nm).

The Horner-Wadsworth-Emmons variant of the Wittig was applied in the synthesis of poly(2,3-diphenyl-1,4-phenylenevinylene) …

Functionalized Sulfone And Sulfonamide Based Poly(Arylene Ether)S, Marina Andrejevic

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A series of fluorinated poly(arylene ether)s, PAE, bearing sulfonated pendent sulfonyl groups, was prepared. A range of Ion Exchange Capacity (IEC) values were achieved by varying the ratios of sulfonated and non sulfonated monomers. Incorporation of both of the monomers was confirmed by NMR spectroscopy and characterization of the thermal properties was done using thermogravimetric analysis (TGA) and differential scanning (DSC). Polymers with these IEC values were synthesized in order to explore their use as a potential alternatives to the widely studied proton exchange membrane, Nafion, with an IEC of 0.91 meq/g.

Using N-phenyl-3,5-difluorobenzene sulfonamide as the starting material a …