9:00 - 9:20 am
Brandon Tessier
Institution: Elizabethtown College
Faculty Mentor: James MacKay
The Aromatic Claisen rearrangement is a widely applicable organic reaction that involves the thermal rearrangement of an allyl phenol to produce ortho-allylated phenols. The goal of this project is to develop a microwave assisted one-pot reaction capable of performing allylation and the Claisen rearrangement in an efficient one-pot synthesis. Microwave assisted organic synthesis employs microwave irradiation to increase reaction rates, which becomes advantageous when performing the thermal Claisen rearrangement. Acetaminophen was chosen as a model phenol to test this chemistry. The optimization of the reaction includes conditions such as time, temperature, solvent, reagents, stoichiometry, the use of other reagents, and the development of an efficient LCMS method for accelerated determination of reaction mixtures. We have developed reaction conditions to obtain greater than 70% yield of isolated rearranged product from acetaminophen, with the goal of exploring alternative phenols.
9:20 - 9:40 am
Mary Lazar
Institution: East Stroudsburg University
Faculty Mentor: Steven Boyer
Supercapacitors have been gaining interest as a method of energy storage due to their ability to quickly charge and discharge compared to batteries. Traditionally, metal oxides would be used as the active material of the electrodes, but they are heavy, expensive to fabricate, and it is hard to alter their specific capacitance without harsh conditions. Conductive polymers are much more flexible, lightweight, cost effective to manufacture, and their specific capacitance can be altered by polymerization conditions. The conductive polymer, poly(3,4-ethylenedioxythiophene)(PEDOT), has high conductivity, good chemical stability, and a lower density compared to other conductive polymers. Our focus is studying the relationship between specific capacitance and thickness of cellulose in a cellulose/PEDOT supercapacitor. The cellulose is produced by K. Xylinus as a byproduct of fermentation. The cellulose produced is flexible, strong, lightweight, and is cost effectively synthesized. Vapor phase polymerization (VPP) is used to create the cellulose/PEDOT electrodes.
9:40 - 10:00 am
Ethan Fessler
Institution: United States Naval Academy
Faculty Mentor: David Durkin
Polyionic biocomposites were prepared through Natural Fiber Welding using the ionic liquid 1-methyl-3-vinylimidazolium methylphosphonate (MVIMPhos) and cotton yarn, with and without microcrystalline cellulose (MCC) binder. The fiber-welded biocomposites were then subjected to anion exchange to alter their water sorption properties. Biocomposite morphology was studied using scanning electron microscopy (SEM) and energy dispersive X-ray spectroscopy (EDS) mapping showed the distribution of anion throughout the matrix. A relative humidity chamber was used to evaluate how each system absorbed water in constant humidity environment.
10:00 - 10:20 am
Kyle D. Shaffer
Institution: West Chester University of Pennsylvania
Faculty Mentor: James Pruitt
Macrophage Migration Inhibitory Factor (MIF) is a cytokine signaling molecule responsible for directing immune cells to a pathogen. Interestingly, the MIF active site is also known to carry out tautomerizations on certain non-natural materials, despite no natural substrate being identified. Several manufactured pharmaceuticals, with the aim of inhibition of MIF, have proven effective in suppression of autoimmune and hyperinflammatory effects caused by the cytokine by binding to this active site. Two such inhibitors, ISO-1 and CPSI-1306, have shown promise in treatment of severe sepsis and carcinoma. A common functionality of both inhibitors is a five-membered isoxazoline ring, but it was hypothesized that efficacy and binding may be further increased with replacement of the isoxazoline ring with a 2-pyrazoline ring. For this reason, an MIF inhibitor homolog was synthesized with the goal of augmenting inhibitory efficacy and was designed to be both functional and customizable at various positions within the structure.
10:20 - 10:40 am
Michael Schnabel
Amal Suleiman Adamu
Institution: University of Maryland Eastern Shore
Faculty Mentor: Victoria Volkis
Pesticide are chemicals that are used in agriculture to prevent and/or control pests. Most of pesticide are toxic, and some may even harm the plant. Due to restriction on pesticide use, organic farms are not allowed to apply synthetic pesticides. As a result, several total harvest losses have happened locally and US wide. Holy basil (Ocimum teniflorum), Aronia (Aronia mitchurinii) and various other herbs and plants are known for their cosmetic and medical use. The effect of Holy basil as an anti-mosquito agent has been also proven. Yet, use of it as potential wide spectrum pesticide has never been studied. We hypothesize, the Holy basil along with other medicinal plants, which may have either a deterrent, attractive or repellent effect on insects. Here we present the extractions from these plants, characterization of the phytochemical content, and use of a bioassay system-controlled pest interference to evaluate pest repellent abilities of extracts.
11:00 - 11:20 am
Jillian Jone
Institution: University of the Sciences
Faculty Mentor: Jeffrey Campbell
A pure tetrahydro-β-carboline phenol intermediate is required for the synthesis of an anticancer clinical candidate. The formation of this intermediate involves a Pictet-Spengler reaction which consists of the reaction between a substituted tryptamine and a 4-O-protected benzaldehyde, a kinetic resolution step, and the removal of an O-aryl protecting group. A promising method uses Pd(0)/Pd(II) and NaBH4 as the reducing scavenger to produce the phenol. However, 25% of the yield comes from a side reaction producing an O-propyl product due to NaBH4 producing hydrogen on Pd(0) causing an olefin reduction. Replacing NaBH4 with NaBH(OAc)3 eliminates the olefin reduction giving a high yield of the desired phenol product. The scope of the reaction was determined through the deprotection of allyl ethers and esters in the presence of different functional groups. These conditions allow the removal of the O-allyl aryl moiety of tetrahydro-β-carboline giving the phenol intermediate in high yield.
11:20 - 11:40 am
Zhiqiao (Kate) Jiang
Institution: University of Pennsylvania
Faculty Mentor: Christopher B Murray
Colloidal semiconductor nanoplatelets (NPLs) are rectangular-shaped, quasi-two-dimensional nanoparticles with bandgaps discretely tunable by the number of atomic layers. Anisotropic NPLs have much narrower photoluminescence peaks compared with more conventional spherical quantum dots (QDs), generating intense interest, but the NPL growth kinetics has not yet been fully explained. This presentation focuses on understanding the growth mechanism of zincblende CdSe NPLs using aliquots isolated periodically from the growth solutions. Optical spectroscopy and electron microscopy are used to characterize the samples. At an early stage of the reaction, QD-like nucleates of different sizes are observed to grow into anisotropic NPLs with uniform thickness through island-nucleation. At a later growth stage, Ostwald ripening is observed when smaller NPLs laterally dissolved to form larger NPLs. The growth mechanism study enables the synthesis of more monodisperse NPLs for better superstructure assembly, which will serve as pure, efficient emitters with properties tunable to individual solid-state devices’ needs.
11:40 - 12:00 pm
Anders Gulbrandson
Institution: United States Naval Academy
Faculty Mentor: David Durkin
In this study, 3-D composites containing methyl methacrylate (MMA) and various mass% of the ionic liquid 1-methyl-3-vinylimidazolium methylphosphonate (MVIMPhos) were printed via sterelithographic (SL) methods. The resultant materials were studied by: (1) scanning electron microscopy (SEM) to evaluate structure/morphology, (2) thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) to study thermal properties/stability, (3) energy dispersive X-ray spectroscopy (EDS) to interrogate distribution of the ionic liquid in the composite matrix. In addition, the materials were exposed to constant humidity (in a relative humidity chamber) to study how ionic liquid content impacted each system’s ability to absorb water.
12:00 - 12:20 pm
Ezra Cable
Institution: University of Maryland Eastern Shore
Faculty Mentor: Victoria Volkis
Aronia mitschurinii is a super-fruit with highest known content of anthocyanin antioxidants. Earlier we have shown that over the period of aronia ripening, the peak of sugars typically comes later than the peak of anthocyanin. However, the color of the berries is the same at both peaks, making it hard to visually determine the optimal time for harvesting for food (highest sugar content), and for medical (highest level of anthocyanins) applications. Our project aims to develop a portable, affordable, easy to use for farmers gauge that can identify anthocyanins and sugar content in berries like aronia. Using a commercial glucometer as a prototype, we have shown that the aronia juice at different visual stages of ripening and the anthocyanin standard can be detected at the natural pH of the juice, whereas sugars in juice can only be detected in neutral buffered solutions. This offers the potential for a glucometer-based gauge.