Organic Chemistry Commons^™

Towards The Synthesis Of Soluble Benzophosphole Oxides Via Addition Of Amine Groups*, Nema Ogal

Campus Research Month

Benzophospholes possess unique properties that make them useful across a wide range of chemical applications, particularly in materials chemistry. Solubilizing benzophosphole oxides would be especially useful in advances in medicinal chemistry. This research is designed to improve the solubility of benzophosphole oxides by adding amino groups which could be protonated and turned to salt. Their synthesis is an ongoing process with many intricate steps, but ultimately very practical outcomes in the filed of organochemistry.

The Stability Study Of Dna-Polymer Hybrids For Nanotechnology Applications, Ethan Kuehn, Milan Jebaraj

Miners Solving for Tomorrow Research Conference

DNA nanostructures have garnered increasing interest in their application as drug delivery vehicles. However, DNA is susceptible to degradation under physiological conditions. To remedy this, we have devised a novel method to coat DNA nanostructures with the polysaccharide chitosan (a natural derivative of chitin). Chitosan binds to DNA electrostatically and inhibits nuclease activity that would normally degrade DNA in a physiological environment. We used both agarose gel electrophoresis (AGE) and atomic force microscopy (AFM) to determine the stability of DNA before and after immersion in a simulated biological environment. Physiological conditions were mimicked by incubating the DNA in cell culture …

Synthesis And Characterization Of Metal Complexes Of Oxindole-Based Β-Lactams, Kenya Rosas, Erick Morales Orrante, Carlos Sifuentes, Alexsei Nazarov

Posters - 2026

• β-lactams are essential structural components of many antibiotics and widely studied due to their biological importance and synthetic versatility.
• The Ugi reaction is a multicomponent reaction, involving a primary amine, carboxylic acid, isocyanide, and an aldehyde or a ketone, that rapidly generates α-acetamido carboxamide derivatives (Ugi adducts).
• The synthesis and characterization of four oxindole-based β-lactam derivatives:
  • 1-Benzyl-N-(tert-butyl)-2-oxo-3-(2-oxoazetidin-1-yl)indoline-3-carboxamide (4a).
  • N-(tert-butyl)-2-oxo-3-(2-oxoazetidin-1-yl)-1-phenylindol-3-carboxamide (4ab).
  • N-(tert-Butyl)-2-oxo-3-(2-oxoazetidin-1-yl)indoline-3-carboxamide (4d).
  • N-(tert-butyl)-1-methyl-2-oxo-3-(2-oxoazetidin-1-yl)indol-3-carboxamide (4e).
• The coordination of the four Ugi adducts with Cu (II) and Ni (II) at different pH points to enhance their stability and improve biological activity.

Co-Ordination Driven Heteroleptic Self-Assembly Of Naphthalene Diimide And Aromatic Dicarboxylate, Rosanna Jees, Kennedy Kuchta, Joshua Do, Erendra Manandhar

Posters - 2026

Co-ordination driven self-assembly is a powerful tool to construct supramolecular co-ordination complexes (SCCs) with predictable and well-defined molecular structures. Fujita, Stang, Newkome, & others have developed novel methodology to synthesize 2D & 3D Metallo-supramolecular structures, such as triangles, cubes, and octahedrons. These have potential applications for optical materials, sensing, catalysis, light harvesting & emissions due to the structures’ well-defined cavity and easy functionalization at the periphery position of ligands.1–4 SCCs with various functional groups, fluorophores, and chromophores, like crown ethers, carbazoles, fullerenes, and dendrimers, have been reported through self-assembly, yet naphthalene-diimide (NDI)-based macrocycles and cages are limited. This project focuses …

Steric And Electronic Considerations Of Ester Hydrolysis: Updating A Longstanding Physical Organic Kinetics Experiment, Mara J. Aucoin

Chemistry Theses

A current, longstanding undergraduate physical chemistry kinetics experiment uses UV-Vis spectrophotometry to follow the hydrolysis of para-nitrophenyl acetate (NPA) with an imidazole (Im) catalyst. The catalyzed and uncatalyzed reaction paths can be studied simultaneously under pseudo first order conditions ([Im]>>>[NPA]). To obtain the rate constants for the catalyzed and uncatalyzed reactions, the concentration of imidazole is varied between reactions and then plotted against the observed rate constant (k_obs).This produces a linear line where the slope is equal to the rate constant of the catalyzed reaction (k_cat) and the intercept is equal to …

Crystallization And Utility Of Brominated Phenylethynylene Bis-Urea Macrocycles, Paras Srivastava

Senior Theses

Macrocycles are large, cyclic molecules with central cavities that can encapsulate other molecules and that have uses in supramolecular chemistry. The Shimizu group has previously synthesized Macrocycle 1, a phenylethynylene bis-urea macrocycle that crystallizes in a columnar form, enabling its utility as a host in host-guest systems. Reactions within these systems can be used to modify stereospecificity, kinetics, and other physical properties. Previously, photodimerization reactions between coumarins and chromones have been studied in systems of Macrocycle 1, resulting in the improved specificity of photodimerization products. Herein, we apply a dynamic covalent chemistry (DCC) strategy to synthesize Macrocycle 1 and its …

Increased Backbone Rigidity Of Artificial Transcription Factors, Jasmine Glover, Emma Otey, Joanna K. Kwao, Nicholas Truex

Senior Theses

Programming DNA-binding proteins is an effective strategy for developing therapeutics that regulate gene expression. These proteins can directly bind to DNA to activate or repress transcription of specific genes. Zinc finger proteins are a class of DNA-binding proteins commonly found in eukaryotic organisms. Their DNA-binding function is derived from unique amino acid sequences within each domain that recognizes specific nucleotides, allowing each finger to selectively recognize three DNA base pairs. Adjoining of multiple domains in tandem allows recognition of a specific DNA sequence. Artificial transcription factors can be made of multiple zinc finger domains arranged in tandem and engineered to …

Synthesis Of Piperidine Heterocycles With Specific Functional Groups Via Sn2 Reactions, Teyanna Monroe

Honors Theses

Piperidine is a heavily utilized nitrogen containing heterocycle found in numerous pharmaceutical agents, solidifying its importance as a building block in drug development. The focus of this research is to investigate different mechanisms of action for adding and replacing various functional groups utilizing readily available lab materials. These findings would lead to determining the overall influence of substitution patterns and functional groups have on stereochemistry, reactivity, and overall conformation of the piperidine ring. The synthetic approach involves the formation of 3-bromo-5-methoxy-tosylpiperidine intermediate through acid promoted cyclization, followed by nucleophilic substitution reactions to introduce various functional groups. Reaction progress and product …

Design And In Silico Modeling Of Heterocyclic-Based Xanthone Derivatives As Potential Anticancer Agents Through Tyrosine Kinase Inhibition, Yehezkiel Steven Kurniawan, Ervan Yudha, Nela Fatmasari, Radite Yogaswara, Harno Dwi Pranowo, Eti Nurwening Sholikhah, Jumina Jumina

Makara Journal of Science

Cancer is one of the deadliest diseases nowadays, and tyrosine kinase receptors play crucial roles in cancer cell survival, differentiation, proliferation, and migration. This study designed and developed a new inhibitor from heterocyclic-based xanthone derivatives to target two tyrosine kinase receptors, epidermal growth factor receptor (EGFR) and platelet-derived growth factor receptor (PDGFR), through in silico screening. Eighteen heterocyclic-based xanthones were evaluated through molecular docking for both receptors. All heterocyclic-based xanthones gave the root mean square deviation (RMSD) value lower than 2.00 Å. Xanthone with isobenzothiazole substituent (iBzThio) was found as the most potent inhibitor with binding energies of -10.60 and …

Top-View Method As A Robust Alternative For Contact Angle Measurement, Bi-Min Zhang Newby, Emmanuel Agyei

University Research

This study validates the top-view method for contact angle measurement, based on the spherical cap assumption, as a practical alternative to conventional side-view techniques. It is particularly useful when side-view imaging is challenging, such as on rough, deformable, irregular, or confined areas where baseline visibility, meridian clarity, or drop symmetry is compromised. To address these challenges, this study details the simultaneous acquisition of top and side-view images of sessile drops along with precise drop volume via drop mass measurements. The contact angles were then deduced from drop volume and contact area based on the spherical cap assumption. Contact angles of …

Physical And Chemical Study Of Interaction In The Urea–Valine System For The Creation Of Modified Liquid Nitrogen Fertilizers, Suvonkul Erkhanovich Nurmonov, Saydullo Khamidovich Azimov

Chemical Technology, Control and Management

This study reports the results of a comprehensive physicochemical investigation of the urea–L-valine binary system, conducted to validate its potential as a modified base for liquid nitrogen fertilizers.

By utilizing the methods of isomolar series, visual-polythermal analysis, X-ray phase (XRD) and single-crystal X-ray diffraction (SC-XRD), synchronous thermal analysis (TGA/DTA), and FT-IR spectroscopy, it was determined that the interaction between components in both aqueous solutions and the solid phase results in the formation of molecular associates stabilized by hydrogen bonds, without the formation of new stoichiometric compounds.

The concentration and temperature limits of the system's stability were defined, revealing a reduction …

An Undergraduate Chemistry Experiment Integrating Theoretical And Practical Aspects Of Hypervalent Iodine(I) Compounds, Vladimir L. Kolesnichenko, Galina Z. Goloverda

Faculty and Staff Publications

A simple reaction sequence has been developed to produce iodine chloride-pyridine (PyICl) and pyridinium dichloroiodate (PyHICl2), convenient iodinating agents, in a high yield. Our approach is safe and simple to handle, avoiding the use of elemental chlorine or hazardous manipulations. Designed for an upper-level undergraduate hybrid lecture/lab chemistry course, the experiment integrates key concepts from both inorganic and organic chemistry. The pre-experiment lecture explains the connections between molecular structure, reactivity trends, and reaction types. Over three 4 h lab sessions, students carry out a sequence of quantitative transformations and characterize each intermediate and the final product using ESI mass spectrometry, …

Monosaccharide Binding To Synthetic Carbohydrate Receptor Microarrays, Milan A. Shlain

Dissertations, Theses, and Capstone Projects

Chapter 1: A glycan detection platform comprised of synthetic carbohydrate receptors (SCRs) immobilized onto polymer brushes was prepared. SCR043, an alkene-containing SCR, was incorporated into grafted-from polymer brushes using hypersurface photolithography, resulting in microarrays of SCR043-functionalized polymer brushes, where brush height (h) and SCR grafting density (Γ) is controlled precisely at each feature in the array. The influence of h and Γ on the binding to five fluorescently labelled monosaccharides – α-glucose (α-Gluc-FL), α-galactose (α-Gal-FL), α-mannose (α-Man-FL), β-glucose (β-Gluc-FL), and β-galactose (β-Gal-FL) – in aqueous buffer …

Development Of Novel Anti-Cancer Colchicine Analogs: Synthesis And Configurational Studies, Orugbani S. Eli

Dissertations, Theses, and Capstone Projects

Colchicine, a naturally occurring alkaloid, has long been known as a potent therapeutic agent. Despite its efficacy treating gout and other inflammatory disorders, its severe toxicity, limited selectivity, and poor pharmacological profile have restricted its broader clinical application. Reported advantages of colchicine-site ligands as vascular-disrupting agents, including reduced susceptibility to multidrug resistance, have revived interest in the colchicine site on tubulin as a validated therapeutic target for cancer. This dissertation focuses on the development of new colchicine analogs, detailing the synthetic method to functionalized AC-ring derivatives, as well as the evaluation of their configurational stability and biological activity.

In Chapter …

Interview With Orca Award Winner Reuben Rieke, Unl Chemistry; Discoverer Of Rieke Metals, Mark Griep, Reuben Rieke

UNL ORCA Interview Series

Emeritus Prof. Reuben Rieke was awarded the ORCA in 1995. Reuben was born in Fairfax, Minnesota. Something in his youth must have sparked an interest in science because he traveled 100 miles east to The University of Minnesota where he earned a bachelor’s in chemistry. Next, he earned a doctorate from the University of Wisconsin, and did postdoctoral work at the University of California Los Angeles. In 1977, after about 11 years as a faculty member in the chemistry department at the University of North Carolina, he joined UNL as a full professor of chemistry. I’ll share two remarkable facts …

Monomeric And Dimeric Metal Complexes Of A New Tridentate Azole-Isoindoline-Urea Ligand, Ben Hudak

Williams Honors College, Honors Research Projects

1,3-Diiminoisoindoline (DII) compounds have been found to be novel materials for both metal binding and chromophore applications. In this work, I am investigating the next synthetic step in developing pyrazole- and indazole-DII compounds. These compounds stem from the reaction of the unsubstituted imine of the pyrazole- or indazole-DII adduct with an isocyanate. These DII compounds, DII-pyrazolePhNCO, DII-pyrazolenapthylNCO, DII-indazolePhNCO, DII-indazolenapthylNCO, DII-pyrazoleptolylNCO, and DII-indazoleptolylNCO were prepared using ethanol as the solvent and heat. Metal acetates were then reacted with the ligands using DMF and heat. The acetate salts included copper (II) and nickel(II). Some distinctive hydrogen bonding interactions were observed in the …

Design, Synthesis, And Characterization Of Phosphonate-Functionalized Diimide Ligands For Metal-Organic Framework Construction, Kenya Rosas, Jonathan Uribe

Posters - 2026

• Metal–organic frameworks (MOFs) are solid, porous materials composed of metalions reacted with organic linkers

• MOFs are customizable through variations in their metal ions, organic linkers, and the functional groups of the organic linker all yielding a structure with different properties

• MOFs have a variety of applications, ranging from storage and catalysis to drug delivery

• The synthesis and characterization of four phosphonate-based diimide ligands:
  • N,N´-bis(phosphonomethyl)-pyromellitimide (PPMI).
  • N,N´-bis(phosphonobenzyl)-pyromellitimide (PPMI-Ph).
  • N,N´-bis(phosphonomethyl)-3,3′,4,4′-biphenylenediimide (PBDI).
  • N,N´-bis(phosphonobenzyl)-3,3′,4,4′-biphenylenediimide (PBDI-Ph).

• These ligands were then coordinated with zinc or copper metal ions to make MOFs.

Superelectrophile Promoted Synthesis Of Heterospirocycles, Mariam A. Adegbenro

Graduate Research Theses & Dissertations

Spirocycles are important scaffolds with a wide range of applications in material science as well as in medicine. The introduction of a heteroatom into the spirocyclic framework can improve its electronic, photophysical, and structural properties. Various reports have been published on the incorporation of atoms other than carbon into the spirocycle. The work outlined in this dissertation involves the development of synthetic methodologies for the synthesis of hetero-spirocycles via superacid-promoted cyclization reactions. These concepts are summarized in Chapter 1.

Chapter 2: Aromatic imines were prepared from 9-fluorenone and azafluorenones, and these substrates were reacted in the Brønsted superacid, triflic acid, …

Using Nmr Spectroscopy And Linear Discriminant Analysis To Molecular Profile Varietal Honey, Taylor Mac

Master's Theses and Doctoral Dissertations

In recent years, varietal honey has been a massive target of adulteration through mislabeling and the addition of other sugars. Unethical companies do this to cut production costs while still charging the consumer full price. Previous studies have used nuclear magnetic resonance (NMR) to unravel possible adulteration in honey, but currently, there are no standard rapid methods to authenticate varietal honey. In our research, we collected NMR signatures (“fingerprints”) and combined them with linear discriminant analysis (LDA) to predict the varietal, country, and region of varietal honey. As a part of the project, we investigated whether an adjustment to the …

Investigating The Role Of Humic Acid In The Adsorption Mechanics Of Acetaminophen On Potassium Persulfate-Aged Polyethylene Terephthalate (Pet), Andrew Littleton, Maria Danielle Garrett, Phd

SPARK Symposium Presentations

Pharmaceutical contaminants such as acetaminophen (APAP) are showing a rising presence in aquatic environments, where their interactions with microplastics (MPs) can potentially modulate natural degradation mechanisms. Concurrent presence of the two substances has been shown to potentiate increase their individual harmful effects. This study investigates whether oxidative aging and humic-acid surface modification of PET microplastics influence APAP adsorption.

In this study, UV-aging was reproduced using an iron (II)-activated potassium persulfate (Fe(II)-KPS) oxidation system. Aqueous dissolved organic matter (DOM) is simulated using multi-hour exposure to humic acid. The MPs are then removed from the solution to examine adsorption mechanisms. While most …