Chemistry Commons^™

Tandem Mass Spectrometric Analysis Of Ammonium And Sodium Oligoperoxide Adducts With The Application Of Two-Dimensional Correlation Spectroscopy And Computational Chemistry, Jessica Lynne Frisch

Electronic Theses and Dissertations

Oligoperoxides, H[OO(CH3)2C]nOOH, are formed as side products in the synthesis of the primary high explosive triacetone triperoxide (TATP). Previous tandem mass spectrometry (MSn ) experiments using a quadrupole ion trap reported that the openchained oligoperoxide adducts of ammonium or sodium resulted in different product ions in the mass spectra. Dissociation mechanisms were previously proposed based on MSn experiments, where n > 2; however, a dissociation pathway achieved by an MSn experiment, where n > 2, may not necessarily be the same pathway achieved in an MS2 experiment. For this dissertation research, the collision induced dissociation pathways were investigated for the open-chained oligoperoxides …

The Behavior Of Cerium Oxide Nanoparticles In Polymer Electrolyte Membranes In Ex-Situ And In-Situ Fuel Cell Durability Tests, Benjamin Pearman

Electronic Theses and Dissertations

Fuel cells are known for their high efficiency and have the potential to become a major technology for producing clean energy, especially when the fuel, e.g. hydrogen, is produced from renewable energy sources such as wind or solar. Currently, the two main obstacles to wide-spread commercialization are their high cost and the short operational lifetime of certain components. Polymer electrolyte membrane (PEM) fuel cells have been a focus of attention in recent years, due to their use of hydrogen as a fuel, their comparatively low operating temperature and flexibility for use in both stationary and portable (automotive) applications. Perfluorosulfonic acid …

Oxidative Stress And Down Syndrome: A Route Toward Alzheimer-Like Dementia, Marzia Perluigi, D. Allan Butterfield

Chemistry Faculty Publications

Down syndrome (DS) is one of the most frequent genetic abnormalities characterized by multiple pathological phenotypes. Indeed, currently life expectancy and quality of life for DS patients have improved, although with increasing age pathological dysfunctions are exacerbated and intellectual disability may lead to the development of Alzheimer's type dementia (AD). The neuropathology of DS is complex and includes the development of AD by middle age, altered free radical metabolism, and impaired mitochondrial function, both of which contribute to neuronal degeneration. Understanding the molecular basis that drives the development of AD is an intense field of research. Our laboratories are interested …

A New Method To Derive Electronegativity From Resonant Inelastic X-Ray Scattering, Stephane Carniato, Loic Journel, Renaud Guillemin, Maria Novella Piancastelli, Wayne C. Stolte, Dennis W. Lindle, Marc Simon

Chemistry and Biochemistry Faculty Research

Electronegativity is a well-known property of atoms and substituent groups. Because there is no direct way to measure it, establishing a useful scale for electronegativity often entails correlating it to another chemical parameter; a wide variety of methods have been proposed over the past 80 years to do just that. This work reports a new approach that connects electronegativity to a spectroscopic parameter derived from resonant inelastic x-ray scattering. The new method is demonstrated using a series of chlorine-containing compounds, focusing on the Cl 2p−1LUMO1 electronic states reached after Cl 1s→LUMO core excitation and subsequent KL radiative decay. Based on …

Hrc Enews — 2012 Winter, Megan M. Iudice

Publications (HRC)

This issue contains staff accomplishments and announcements, event listings, and a "new faces" listing for new staff, affiliates, and researchers.

Functionalized Ruthenatricarbadecaborane Via Selective Cage Iodination And Sonogashira Coupling Reactions, Ariane Perez-Gavilan, Larry Sneddon, Patrick J. Carroll

Articles

Selective iodination of the cyclopentadienylruthenium tricarbadecaboranyl complexes 1-(η5-C5H5)–2-Ph–closo-1,2,3,4-RuC3B7H9 (1) and 1-(η5-C5(CH3)5)–2-Ph–closo-1,2,3,4-RuC3B7H8 (2) to form their mono-iodo derivatives, 1-(η5-C5H5)–2-Ph–6-I–closo-1,2,3,4-RuC3B7H9 (3) and 1-(η5-C5(CH3)5)–2-Ph–6-I–closo-1,2,3,4-RuC3B7H8(4), was achieved in 90% yields by their reactions with ICl in CH2Cl2 solutions. Also isolated in trace amounts from the reaction with 2 was the di-iodo 1-(η5-C5(CH3)5)–2-Ph–6,11-I2–closo-1,2,3,4-RuC3B7H7, (5) complex. The sonication-promoted Sonogashira coupling reaction of 3 with terminal acetylenes catalyzed by Pd(dppf)Cl2/CuI yielded the functionalized ruthenatricarbadecaboranyl complexes 1-(η5-C5H5)–2-Ph–6-(Ph-C≡C)–closo-1,2,3,4-RuC3B7H8 (6), 1-(η5-C5H5)–2-Ph–6-[CH3CH2C(O)OCH2-C≡C]–closo-1,2,3,4-RuC3B7H8 (7), …

Volume 04, Matt Szemborski, Phillip Van Ness, Sarah Croughwell, Sarah Mayfield, Alyssa Strackbein, Marley Kimmel, Stephanie Skipp, Jamie Yurasits, Katherine Taggart, Alex Leonhart, Kristen Rawls, Andrew Armes, Amanda Haymens, Allison Paqlowski, Erica May, Stephanie Lane, Luke Acree, Cassandra L. Wilson, Stephanie Pishock, Erica Hopson, K. Juston Osborne, Katheryn Grayson, Kyle Fowlkes, Jessica Cox, Kaity Byrum, John-Harwood Scott, Ashley Johnson, Samantha Hockman, Emily Staskiel, Nancy Macdonald, R. Kruger Bressin, Benjamin P. Bilodeau, Andrea Irby, Kristin Macquarrie, Sarah Bietsch, Elizabeth Bednar

Incite: The Journal of Undergraduate Scholarship

Please note that part of pages 92-95 are redacted, in the digital copy, due to a misprint of the original printed article.

Introduction from Dean Dr. Charles Ross

The Internal Other: Transculturation and Postcolonial Magical Realism in Rushdie’s Midnight’s Children by Matt Szemborski

Photography by Phillip Van Ness

Photography “Waterfall” by Sarah Croughwell

Romancing the Bite: Statistical Analysis of Young Adult Vampire Novels by Sarah Mayfield

Photography by Alyssa Strackbein

Photography by Marley Kimmel

Wine and Society in the Viceroyalty of Peru by Stephanie Skipp

Analysis of Claud Monet’s Impression, Sunrise by Jamie Yurasits

Exploring Meaning: The Lindisfarne Gospels by …

Ruthenium Polypyridyl Complexes That Utilize Azo-Dyes To Enhance Absorption Of Visible Photons, Akram Hazeen

Masters Theses

Research in the field of dye sensitized solar cells has been growing rapidly. The challenge in this field is to prepare molecules that absorb in the visible region. An azo dye ligand based on l,0-phenanthroline, "phen-azo-phenol", was prepared and found to absorb at 380 nm in MeOH. UV-Vis spectra of this ligand were recorded in different solvents and in the presence of added acid or base and it appeared that the spectra were shifted to longer wavelength (around 500 nm) in the presence of base and/or basic solvents. This was attributed to deprotonation of the phenol portion of the ligand. …

Utilization Of Phosphorus Ylides Towards The Synthesis Of Extended Cinnamaldehydes And Stellettins, John M. Saathoff

Masters Theses

Phosphorus ylides have been utilized in three synthetic approaches; two involving the synthesis of photochromic cinnamaldehyde semicarbazones and a final scheme towards the synthesis of the isomalabaricane natural products. The targeted cinnamaldehyde semicarbazones varied both in the length of the conjugated system as well as the position and type of phenyl ring substituents, because these variations could impact their degree of photochromicity. The three step synthesis of the extended cinnamaldehyde semicarbazones involved a Wittig condensation, hydrolysis of acetal protecting group, and formation of imine and was completed in respectable cumulative yields; 42.4% yield for semicarbazones with n = 1 double …

Electrochemical Characterization Of Thin-Film Perovskite-Type La1-Xsrxmno3 Electrodes Obtained By Pulsed Laser Deposition (Pld), Keerthi Chandra

Masters Theses

The implementation of fuel cells into commercial usage is prenominally dependent on the activity of cathode at which oxygen reduction reaction (ORR) takes place. Fuel cells currently use noble metals like platinum, palladium etc as cathode for the reduction reaction. These metals showed poor performance during changes in red ox environment. Perovskite oxides which were proven to be efficient as cathodes in solid oxide fuel cells operating at high temperature was studied to understand its ability to carry out ORR in alkaline fuel cells operating at room temperature.

La_1-XSr_xMnO₃ (LSMO), thin film perovskite oxide, a …

Simultaneous Electrochemical Determination Of Tryptamine And Barbituric Acid, Luxshani Thangarajah

Masters Theses

The ability to analyze mixtures of two or more red-ox active components "on-the-spot" without the need to carry the sample into a laboratory is typically limited by the fact that various components need to be separated before they can be quantified. Reducing the two-step protocol (separation and detection) to a single one (detection) would markedly shorten the analysis time and simplify the analysis.

Exploring Phenyl Embrace Interactions In Trityloxy And Tritylamino Aromatic Compounds, Premnath Basa

Masters Theses

The area of supramolecular chemistry seeks to understand the organization of molecular structures and the interactions that hold such assemblies together by non-covalent interactions such as electrostatic, hydrogen bonding, π-π stacking interactions, and hydrophobic or solvatophobic effects. One such example that comes under supramolecular chemistry is the phenyl embrace interaction. These interactions occur due to the cooperative participation of at least three or more neighboring phenyl groups arranged as an interlocking propeller configuration to give complementary edge-to-face or offset face-to-face interactions. In order to understand the effect of functional groups on the tendencies of organic compounds to form phenyl embrace …

Photochemistry And Applications Of Diels-Alder Adducts And Photoacids In Materials Science, Valentine Johns

Electronic Theses and Dissertations

In chapter I Photo-retro-Diels-Alder (PrDA) reactions of a variety of Diels Alder (DA) adducts were studied. Experimental results showed that the photoreactivity (quantum yield) depends on the electron-donating ability of the diene component and the electronwithdrawing ability of the dienophile component. The mechanism was studied by trapping the reaction intermediate, O2 quenching and femtosecond time-resolved absorption spectroscopy. All the results support a mechanism that involves a charge-separated intermediate generated from a singlet excited state. The PrDA reaction may find applications in photoresponsive materials, photolithography, drug delivery and mechanistic research. Chapter II shows two applications of the PrDA reaction. The first, …

Parallel Text Immersion, Daniel P. Becker Ph.D.

Chemistry: Faculty Publications and Other Works

A new method of teaching foreign languages to beginning, intermediate, and advancing foreign language students is proposed involving reading out loud passages, chapters, and entire works of literature that are familiar to the student through required pre-reading in the students’ mother tongue. Testing is proposed to evaluate the success of the method.

Conformational And Thermodynamic Properties Modulate The Nulceotide Excision Repair Of 2-Aminofluorene And 2-Acetylaminofluorene Dg Adducts In The Nari Sequence, Vipin Jain, Benjamin Hilton, Satyakam Patnaik, Yue Zou, M. Paul Chiarelli, Bongsup P. Cho

Chemistry: Faculty Publications and Other Works

Nucleotide excision repair (NER) is a major repair pathway that recognizes and corrects various lesions in cellular DNA. We hypothesize that damage recognition is an initial step in NER that senses conformational anomalies in the DNA caused by lesions. We prepared three DNA duplexes containing the carcinogen adduct N-(2'-deoxyguanosin-8-yl)-7-fluoro-2-acetylaminofluorene (FAAF) at G(1), G(2) or G(3) of NarI sequence (5'-CCG(1)G(2)CG(3)CC-3'). Our (19)F-NMR/ICD results showed that FAAF at G(1) and G(3) prefer syn S- and W-conformers, whereas anti B-conformer was predominant for G(2). We found that the repair of FAAF occurs in a conformation-specific manner, i.e. the highly S/W-conformeric G(3) and -G(1) …

A Seminaphthofluorescein-Based Fluorescent Chemodosimeter For The Highly Selective Detection Of Cysteine, Xiaofeng Yang, Yixing Guo, Robert M. Strongin

Chemistry Faculty Publications and Presentations

A fluorescent chemodosimeter for cysteine detection was developed based on a tandem conjugate addition and intramolecular cyclization reaction. The method exhibited an excellent selectivity for cysteine over other biothiols such as homocysteine and glutathione.

Overview Of The 2010 Carbonaceous Aerosols And Radiative Effects Study (Cares), Rahul A. Zaveri, William J. Shaw, Daniel J. Cziczo, Beat Schmid, Richard Ferrare, M. Lizabeth Alexander, Raul Alvarez, W. Patrick Arnott, Dean B. Atkinson, Sunil Baidar, Robert M. Banta, James Barnard, Josef Beranek, Larry K. Berg, Fred Brechtel, W. Alan Brewer, John F. Cahill, Brian Cairns, Christopher D. Cappa, D. Chand, S. China, Jennifer M. Comstock, Manvendra K. Dubey, Robert C. Easter, M. H. Erickson, Jerome Fast, Cody Floerchinger, B. Flowers, Edward C. Fortner, Jeffrey S. Gaffney, Mary K. Gilles, Kyle Gorkowski, William Gustafson, Madhu Gyawali, J. Hair, R. M. Hardesty, Joseph Harworth, Scott C. Herndon, Naruki Hiranuma, Chris Hostetler, John M. Hubbe, John T. Jayne, H. Jeong, B. Tom Jobson, Evgueni Kassianov, Lawrence I. Kleinman, C. Kluzek, W. Berk Knighton, Katheryn R. Kolesar, Chongai Kuang, Alena Kubátová, Andrew O. Langford, Alexander Laskin, N. Laulainen, Richard D. Marchbanks, Claudio Mazzoleni, Fan Mei, Ryan C. Moffet, Dan Nelson, Michael Obland, Hilke Oetjen, Timothy B. Onasch, I. Ortega, Matteo Ottaviani, Mikhail Pekour, Kimberly A. Prather, James Gregory Radney, Raymond R. Rogers, Scott P. Sandberg, Arthur J. Sedlacek, Christoph J. Senff, Gunnar I. Senum, Ari Setyan, John E. Shilling, Manishkumar Shrivastava, C. Song, Stephen R. Springston, R. Subramanian, Kaitlyn Suski, Jason Tomlinson, Rainer M. Volkamer, H. W. Wallace, Jian Wang, A. M. Weickmann, Douglas R. Worsnop, Xiao-Ying Yu, Alla Zelenyuk, Qi Zhang

Chemistry Faculty Publications and Presentations

Substantial uncertainties still exist in the scientific understanding of the possible interactions between urban and natural (biogenic) emissions in the production and transformation of atmospheric aerosol and the resulting impact on climate change. The US Department of Energy (DOE) Atmospheric Radiation Measurement (ARM) program’s Carbonaceous Aerosol and Radiative Effects Study (CARES) carried out in June 2010 in Central Valley, California, was a comprehensive effort designed to improve this understanding. The primary objective of the field study was to investigate the evolution of secondary organic and black carbon aerosols and their climate-related properties in the Sacramento urban plume as it was …

Selective Multivariate Applications In Forensic Science, Caitlin Rinke

Electronic Theses and Dissertations

A 2009 report published by the National Research Council addressed the need for improvements in the field of forensic science. In the report emphasis was placed on the need for more rigorous scientific analysis within many forensic science disciplines and for established limitations and determination of error rates from statistical analysis. This research focused on multivariate statistical techniques for the analysis of spectral data obtained for multiple forensic applications which include samples from: automobile float glasses and paints, bones, metal transfers, ignitable liquids and fire debris, and organic compounds including explosives. The statistical techniques were used for two types of …

A Study Of The Degradative Capabilities Of The Bimetallic System: Mg(Pd/C) As Applied In The Destruction Of Decafluoropentane, An Environmental Contaminant, Douglas Tomlin

Electronic Theses and Dissertations

Pollution from hydrofluorocarbons (HFC) poses a serious challenge to the environmental community. Released from industrial operations, they have contaminated both the atmosphere and groundwater and are considered persistent in both media.1 For over the past 20 years, the practice of synthesizing hydrofluorocarbons as alternatives to chlorofluorocarbons (CFC) has been conducted in an effort to reverse the effects of stratospheric ozone layer depletion. 2,3 However, in doing so these new fluorinated compounds exhibited an unexpected property as a potent global warming greenhouse gas (GHG) with radiative forcing potentials in the range of 100 to 10,000 equivalents greater than carbon dioxide.4 Conversely, …

Assessment Of Molecular Interactions Via Magnetic Relaxation: A Quest For Inhibitors Of The Anthrax Toxin, Oscar Santiesteban

Electronic Theses and Dissertations

Anthrax is severe disease caused by the gram-positive Bacillus anthracis that can affect humans with deadly consequences. The disease propagates via the release of bacterial spores that can be naturally found in animals or can be weaponized and intentionally released into the atmosphere in a terrorist attack. Once inhaled, the spores become activated and the anthrax bacterium starts to reproduce and damage healthy macrophages by the release of the anthrax toxin. The anthrax toxin is composed of three virulent factors: (i) anthrax protective antigen (APA), (ii) anthrax lethal factor (ALF), and (iii) anthrax edema factor (AEF) that work in harmony …

Performance Evaluation And Characterization Of Symmetric Capacitors With Carbon Black, And Asymmetric Capacitors Using A Carbon Foam Supported Nickel Electrode, Jinjin Wang

Dissertations, Master's Theses and Master's Reports - Open

This thesis evaluates a novel asymmetric capacitor incorporating a carbon foam supported nickel hydroxide positive electrode and a carbon black negative electrode. A series of symmetric capacitors were prepared to characterize the carbon black (CB) negative electrode. The influence of the binder, PTFE, content on the cell properties was evaluated. X-ray diffraction characterization of the nickel electrode during cycling is also presented.

The 3 wt% and 5 wt% PTFE/CB symmetric cells were examined using cyclic voltammetry (CV) and constant current charge/discharge measurements. As compared with symmetric cells containing more PTFE, the 3 wt% cell has the highest average specific capacitance, …

Coordination Chemistry Of Bis(Benzyl)Phosphinate, John S. Maass

Dissertations, Master's Theses and Master's Reports - Open

The work presented in this dissertation deals with the coordination chemistry of the bis(benzyl)phosphinate ligand with vanadium, tungsten and cobalt. The long term goal of this project was to produce and physically characterize high oxidation state transition metal oxide phosphinate compounds with potential catalytic applications.

The reaction of bis(benzyl)phosphinic acid with VO(acac)₂ in the presence of water or pyridine leads to the synthesis of trimeric vanadium(IV) clusters (V₃(µ₃-O)O₂)(µ₂-O₂P(CH₂C6H5)₂)₆(H2O) and (V₃(µ₃-O)O₂)(µ₂-O₂P(CH₂C_{6 …}

Organometallic Heterocycles And Acene-Quinone Complexes Of Ruthenium, Iron And Manganese, Uttam Raj Pokharel

Theses and Dissertations--Chemistry

A variety of organometallic-fused heterocycles and acene quinones were prepared and characterized. This work was divided into three parts: first, the synthesis of 5,5-fused heterocyclic complexes of tricarbonylmanganese and (1’,2’,3’,4’,5’-pentamethylcyclopentadienyl)ruthenium; second, the synthesis of 1,2-diacylcyclopentadienyl p-cymene complexes of ruthenium(II); and third, synthesis of cyclopentadienyl-fused polyacenequinone complexes of ruthenium, iron and manganese.

The first examples of the convenient, versatile and symmetric cyclopentadienyl-fused heterocycle complexes of (1’,2’,3’,4’,5’-pentamethylcyclopentadienyl)ruthenium(II) and tricarbonylmanganese(I) were synthesized starting from (1,2-dicarbophenoxycyclopentadienyl)sodium. The sodium salt was transmetalated using [MnBr(CO)₅] and 1/4 [Ru(μ3-Cl)(Cp*)]₄ to give [Mn(CO)₃{η⁵-C₅H₃(CO₂Ph)₂-1,2}] …

How A Silent Mutation Suppresses The Activity And Iron Incorporation In Superoxide Dismutase, Xiaonan Mei

Theses and Dissertations--Chemistry

A mutation (CTG to TTG) of FeSOD gene was found in Escherichia coli. Since they both encode leucine, it is a silent mutation. Site-­‐directed mutagenesis was applied to correct the mutation, and the mutant FeSOD (before gene correction) and wild type FeSOD (after gene correction) were purified. The FeSODs from the two genes were Characterized using different assays and spectroscopic methods including EPR and CD. The requirement for the rare codon TTG may result in slowed translation and heavy demand on a scarce tRNA. Cultures expressing wild type FeSOD are better able to grow for long times after addition of …

Investigations Into Modulation Of Brain Oxidative Stress By Various Interventions, Jessica Lynn Harris

Theses and Dissertations--Chemistry

In this thesis study we examined glycogen synthase kinase-3β (GSK-3β) and its effects over Nrf2 and Pin 1 as it relates to Alzheimer’s disease (AD). AD is a neurodegenerative disease characterized by a prolonged high oxidative environment. Transcription factor Nrf2 is vital in the brain’s defense against oxidative insults through its up-regulation of over 100 antioxidants. Depletion of the brain’s antioxidant defense system results in intolerance to an oxidative environment, contributing to the progression of AD. The regulatory Pin 1 protein promotes cellular homeostasis, and when down-regulated results in increased deposits of neurofibrillary tangles (NFTs) and amyloid-β (Aβ) plaques, the …

Bifunctional Bisphosphonates For Delivering Biomolecules To Bone, Jivan N. Yewle

Theses and Dissertations--Chemistry

Active targeting with controlled delivery of therapeutic agents to bone is an ideal approach for treatment of several bone diseases. Since bisphosphonates (BPs) are known to have high affinity to bone mineral and are being widely used in treatment of osteoporosis, they are well-suited for drug targeting to bone. For this purpose, bifunctional hydrazine-bisphosphonates (HBPs) with spacers of various lengths and lipophilicity were synthesized and studied. Crystal growth inhibition assays demonstrated that the HBPs with shorter spacers bound more strongly to bone mineral, hydroxyapatite (HA), than did alendronate. HBPs were also demonstrated to be non-toxic to MC3T3-E1 pre-osteoblasts. The targeted …

Investigations Of Oxidative Stress Effects And Their Mechanisms In Rat Brain After Systemic Administration Of Ceria Engineered Nanomaterials, Sarita S. Hardas

Theses and Dissertations--Chemistry

Advancing applications of engineered nanomaterials (ENM) in various fields create the opportunity for intended (e.g. drug and gene delivery) or unintended (e.g. occupational and environmental) exposure to ENM. However, the knowledge of ENM-toxicity is lagging behind their application development. Understanding the ENM hazard can help us to avoid potential human health problems associated with ENM applications as well as to increase their public acceptance. Ceria (cerium [Ce] oxide) ENM have many current and potential commercial applications. Beyond the traditional use of ceria as an abrasive, the scope of ceria ENM applications now extends into fuel cell manufacturing, diesel fuel additives …

Removal Of Arsenic(Iii) From Water With A New Solid-Supported Thiol, Partha Jana

Theses and Dissertations--Chemistry

Arsenic is a highly toxic, easily transportable and widespread contaminant in groundwater throughout the world. Arsenic causes acute toxicity by disrupting biological functions. In groundwater arsenic concentrations can reach up to a few milligrams per liter. Current regulations on arsenic content in drinking water are becoming more stringent and require the standard to be reduced to a few parts per billion. Arsenic exists as oxyanions in aqueous solution in either trivalent or pentavalent oxidation states depending on the oxidation-reduction potential and pH of the medium. Several treatment methods are available for removing arsenic from water. However, cost, operational complexity of …

Biosensing Systems For The Detection Of Bacterial Quorum Sensing Molecules: A Tool For Investigating Bacteria-Related Disorders And Food Spoilage Prevention, Nilesh G. Raut

Theses and Dissertations--Chemistry

Quorum sensing enables bacteria to communicate with bacteria of the same or different species, and to modulate their behavior in a cell-density dependent manner. Communication occurs by means of small quorum sensing signaling molecules (QSMs) whose concentration is proportional to the population size. When a QSM threshold concentration is reached, certain genes are expressed, thus allowing control of several processes, such as, virulence factor production, antibiotic production, and biofilm formation. Not only many pathogenic bacteria are known to produce QSMs, but also QSMs have been identified in some bacteria-related disorders. Therefore, quantitative detection of QSMs present in clinical samples may …

Synthesis And Characterization Of Functionalized Naphthalenes And Anthracenes, Guang Zhang

Theses and Dissertations--Chemistry

Organic electronics have received significant development in the last few decades. p- Type materials are much more in availability than n-type now. There are only a few examples of air-stable n-type materials. The design and synthesis of novel air-stable ntype materials is still a focus of research. Herein is described a study to evaluate the effectiveness of a novel electron-withdrawing group, composed of three electronwithdrawing groups connected in series, to impart material properties known to be favorable for obtaining air-stable n-types. The smaller acenes, naphthalene and anthracene, carrying these electron-withdrawing groups were prepared and studied by UV-Vis absorption spectroscopy and …