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Tailoring Selected Aerogels To Targeted Applications, Stephen Yaw Owusu

Doctoral Dissertations

Aerogels are ultra-lightweight, porous solid materials characterized by a three-dimensional nanostructured network. Owing to their exceptional physical and chemical properties, aerogels have garnered considerable attention within the materials science community and were recognized by IUPAC in 2022 as one of the top ten emerging technologies in chemistry. Although numerous aerogels have been synthesized, only a few have been effectively tailored for specific applications. Optimizing the properties of known aerogels for targeted uses remains challenging. This dissertation investigates strategies for tailoring aerogels derived from isocyanate-benzoxazine, benzodiazine, and phenolic resins to meet the requirements of various advanced applications. The approaches employed include …

Lead-Free Alternatives And Toxicity Mitigation Strategies For Sustainable Perovskite Solar Cells: A Critical Review, Md Helal Miah, Mayeen Uddin Khandaker, Md Jakir Hossen, None Noor-E-Ashrafi, Ismat Jahan, Md Shahinuzzaman, Mohammad Nur-E-Alam, Mohamed Y. Hanfi, Md Habib Ullah, Mohammad Aminul Islam

Research outputs 2022 to 2026

The growing global energy demand has prompted an increase in research into renewable energy conversion technologies. Although lead-based perovskite solar cells (PSCs) offer high efficiency as well as low manufacturing costs, the toxicity of the material is still a serious hurdle to their commercialization and widespread adoption. Amid ongoing efforts to develop lead-free perovskites, over the last few years, growing attention on mitigating the toxicity of lead by inhibiting the leakage of lead from PSCs has been observed. This review discusses the potential replacement of lead from PSCs and explores various approaches to mitigate lead leakage from PSCs. In addition, …

Re-Crosslinkable Particle For Conformance Control And Temporary Plugging, Yifu Long, Bowen Yu, Baojun Bai, Thomas P. Schuman

Patents

The present invention generally relates to the composition of particle gels for conformance control, well drilling and well treatments. More particularly, this invention relates to swellable polymer particle gels that can re-crosslink, i.e., reassociate and self-heal, at subterranean conditions. These particle gels can be deployed to improve the conformance of water flooding of especially matrix bypass events (MBEs), that are also known as void space conduits. Moreover, these particle gels can be deployed for controlling the water production and increasing of petroleum recovery. The inventive particles can also be deployed as diverter for well stimulation.

Disaggregation Of Nanodiamond Particles, Vadym Mochalin, Atsushi Kume, Yoshihiro Inamoto, Masumi Hashimoto

Patents

Methods for disaggregating nanodiamond clusters, for example, by using sonication to break apart nanodiamond aggregates in an aqueous slurry having an alkaline pH. Compositions, such as aqueous nanodiamond dispersions and dry particulate compositions can be produced using these methods.

Coating Compositions And Methods For Using The Same, Fateme Razaei, Thomas P. Schuman, Glenn C. Morrison

Patents

Coating compositions and methods for using the same are disclosed. The coating compositions can include an aminosilica adsorbent. The coating compositions can adsorb CO2 .

Metal-Free Photoredox Catalysis For The S-Trifluoromethylation Of Thiols, Raheemat Rafiu, Puspa Aryal, V. Prakash Reddy

Chemistry Faculty Research & Creative Works

The S-trifluoromethylation of thiols is accomplished using a simple and cost-effective organic catalyst (diacetyl) along with a bench-stable and environmentally friendly trifluoro methylating reagent (Langloi's reagent). Under optimized conditions (2.5 equivalents of Langlois reagent, Blue LED irradiation, 48-h reaction time at room temperature), the reaction yielded up to 81% S-trifluoro methylated product. This method's high yields, compatibility with a broad substrate scope (aliphatic, heteroaromatic, and aromatic thiols), and environmentally friendly conditions demonstrate its potential for broader synthetic applications. In contrast to traditional methods that rely on organometallic catalysts and environmentally hazardous reagents, this novel photoredox catalysis method offers a more …

Characterizing The Transient Emission Of Particles And Gases From A Single Puff Of Electronic Cigarette Smoke, Kashala Fabrice Kapiamba, Steven Achterberg, Ta Chun Lin, Philip D. Whitefield, Yue-Wern Huang, Yang Wang

Chemistry Faculty Research & Creative Works

This study employed high-time-resolution systems to examine the transient properties of aerosols and gases emitted from electronic cigarette (EC) puffs. Using a fast aerosol sizer, we measured particle size distributions (PSDs) across various EC brands (JUUL, VUSE, VOOPOO), revealing sizes ranging from 5 to 1000 nm at concentrations of 107 to 1010 cm-3. Most aerosols were found to be in the ultrafine range (below 100 nm), with JUUL-, VUSE-, and VOOPOO-producing aerosols with geometric mean sizes of 19.9, 47.3, and 29.4 nm, respectively. Applying the International Commission on Radiological Protection (ICRP) deposition model and assuming no further evolution of aerosols …

Nontoxic High Temperature Resistant Hydrogels, Thomas P. Schuman, Baujun Bai, Buddhabhushan Pundlik Salunkhe

Patents

Compositions of swellable non-toxic hydro gels and their use in conformance control are described herein. More specifically, the present invention generally relates to the hydro gels compositions that can be used to treat the oil reservoirs having high temperature and high salinity conditions. The compositions generally comprise a plurality of swellable particles having one or more crosslinkers interspersed within a polymer matrix. The compositions can also be used in biomedical, agricultural, fracking and similar applications wherein thermally-stable, nontoxic hydrogels are required.

Extreme Value Theory Analysis Of High Emitter Trends Across Four Us Cities From 1995 To 2021, M. Matti Maricq, Gary A. Bishop

Fuel Efficiency Automobile Test Publications

Extreme value theory provides a direct means to characterize the distribution of high emitters within a vehicle fleet and calculate statistical confidence intervals for comparisons. Defining a “high emitter” as the maximum emitter in a random sample of N vehicles implies in the limit of large N that high emitters follow an extreme value distribution, comprised of three distinct domains. The analysis of over twenty years of roadside remote sensing emissions measurements in Chicago, Denver, Los Angeles and Tulsa reveals clear differences between gasoline vehicle high emitter distributions across pollutants (hydrocarbons (HC), carbon monoxide (CO) and nitric oxide (NO)), but …

Thermo-Rheological And Tribological Properties Of Low- And High-Oleic Vegetable Oils As Sustainable Bio-Based Lubricants, Abiodun Saka, Tobechukwu K. Abor, Anthony C. Okafor, Monday U. Okoronkwo

Mechanical and Aerospace Engineering Faculty Research & Creative Works

Vegetable oil-based lubricants have attracted increased research attention in recent decades as sustainable alternatives to conventional petroleum-based lubricants in metal machining. However, more studies are required to fully elucidate the thermo-rheological and tribological properties. This study presents an investigation of the thermo-rheological and tribological properties of different vegetable oils, including low- and high-oleic soybean oil, high-oleic sunflower, safflower, and canola oils. The lubricity, and evolution of viscosity and thermodynamic properties as a function of temperature were investigated to obtain important parameters including the viscosity index, flow behavior index, flow activation energy, specific heat capacity, thermal conductivity, coefficient of friction, contact …

Instantaneous Hydrolysis Of Methyl Paraoxon Nerve Agent Simulant Is Catalyzed By Nontoxic Aminoguanidine Imines, Emmanuel Kingsley Darkwah, Puspa Aryal, Chi Zhang, Charles B. Musgrave, William A. Goddard, V. Prakash Reddy

Chemistry Faculty Research & Creative Works

Exposure to organophosphate-based nerve agents and pesticides poses health and security threats to civilians, soldiers, and first responders. Thus, there is a need to develop effective decontamination agents that are nonhazardous to human health. To address this, we demonstrate that instantaneous hydrolysis of methyl paraoxon (Me-POX), a nerve agent simulant, can be achieved in the presence of aminoguanidine imines at pH 10: ● the pyridine-4-aldehyde aminoguanidine-imine (1) and ● the 2,3-butanedione aminoguanidine-imine (2). The hydrolysis of Me-POX under these conditions is substantially faster than that of the state-of-the-art decontaminating agent, Dekon-139 (2,3-butanedione oxime, potassium salt). Furthermore, Dekon-139 shows adverse effects …

Synthesis And Characterization Of Eco-Engineered Hollow Fe2o3/Carbon Nanocomposite Spheres: Evaluating Structural, Optical, Antibacterial, And Lead Adsorption Properties, Islam Gomaa

Nanotechnology Research Centre

This work presents a facile mechano-thermal route for the synthesis of carbon-decorated, hollow, mesoporous α-Fe2O3 microspheres. Comprehensive characterization (XRD, XPS, FT-IR, SEM/EDX, TGA, zeta-potential) confirmed the formation of phase-pure hematite with nanoscale crystallites (~19 nm), substantial residual surface carbon (~40 wt%) consistent with Fe–O–C linkages, and a positive surface charge (+15.9 mV). The hierarchical hollow/mesoporous architecture enables fast ion transport and provides extensive interior binding sites, resulting in rapid Pb(II) uptake that reaches 92% removal in ≈15 min at pH 5.0. The adsorption follows a Langmuir isotherm (qmax ≈ 70.6 mg/g) and pseudo-second-order kinetics, indicative of chemisorption coupled to efficient …

Functionalized 2d Hexaazatriphenylene As Hydrogen Storage Platform: A Dft-Guided Design Approach, Islam Gomaa

Nanotechnology Research Centre

No abstract provided.

First-Principles Modeling Of Nitazoxanide Analogues As Prospective Pfor-Targeted Antibacterials, Islam Gomaa

Nanotechnology Research Centre

Pyruvate:ferredoxin oxidoreductase (PFOR) is a key Achilles’ heel in anaerobic pathogens. We integrate electronic-structure calculations (DFT), cheminformatic QSAR metrics, and residue-resolved docking to distill a concise “recognition code” and translate it into practical design rules. Using nitazoxanide (Nita; ΔG(bind) ≈ −10.0 kcal·mol−1) as a well-established reference, productive binding requires a conserved triad: a hydrogen-bond donor addressing Thr-997 and Cys-840, a π–π stack with Phe-869, and a recurrent π–σ contact to Thr-997 that orients the scaffold. Deacetylation to tizoxanide unmasks the phenolic donor and raises local electrophilicity, yet it also slightly loosens pocket packing (−9.6 kcal·mol−1). Strategic halogenation introduces a σ-hole …

Oriented Surface Immobilization Of Antibodies Using Enzyme-Mediated Site-Specific Biotinylation For Enhanced Antigen-Binding Capacity, Emily Beitello, Kwame Osei, Trent Kobulnicky, Faith Breausche, Jon A. Friesen, Jeremy D. Driskell

Faculty Publications – Chemistry

The effectiveness of surface-immobilized antibodies is often diminished by improper antibody orientation and limited stability, impeding the analytical performance of biosensors. Here, we report a novel enzyme-mediated strategy to biotinylate the Fc region of an anti-horseradish peroxidase (anti-HRP) antibody with site-specificity that enables oriented immobilization on a streptavidin-functionalized surface. Microbial transglutaminase (mTG) catalyzes the covalent coupling between the amine functional group on a biotin analogue (NH₂-PEG₄-biotin) and the side chain of a privileged glutamine residue (Q295) located on the heavy chain Fc region of IgG antibodies. For comparison, an anti-HRP antibody was biotinylated using an amine-reactive …

Synthesis Of Phenaliporphyrin, A Pah-Porphyrin Hybrid, From An Acenaphthene-Fused Cyclopropane Dialdehyde, Sunday Oladapo Jacob, Emily D. Harris, Melissa A. Mathius, Deyaa I. Abusalim, Gregory M. Ferrence, Timothy D. Lash

Faculty Publications – Chemistry

Phenaliporphyrin, a new aromatic benziporphyrin derivative, has been synthesized from an annulated cyclopropane dialdehyde intermediate. Corey-Chaykovsky cyclopropanation of dimethyl acenaphthylene-1,2-dicarboxylate gave a cyclopropane diester, and this was converted to the corresponding bis-Weinreb amide. Reduction with lithium aluminum hydride afforded an unstable dialdehyde and subsequent acid-catalyzed condensation with a tripyrrane dicarboxylic acid, followed by oxidation with aqueous ferric chloride, gave the targeted porphyrinoid system. This involves ring expansion of the acenaphthylene precursor to generate the phenalene unit. Phenaliporphyrin exhibits a porphyrin-like UV–vis spectrum with a Soret band at 443 nm and a relatively intense Q-band at 601 nm. The proton NMR …

Automatic Identification And Visualization Of Reaction Mechanisms Contained Within Direct Dynamics Simulations, Trent Kobulnicky, Emmanuel Boafo, George L. Barnes

Faculty Publications – Chemistry

Direct dynamics simulations are employed in many areas of chemistry and biochemistry. When paired with an appropriate underlying ab initio, semiempirical, or DFT-based potential energy surface and proper sampling of initial conditions, direct dynamics simulations provide an atomic-level view of the reaction dynamics within the system of interest, yielding considerable fundamental insights. Moreover, when a sufficient number of simulations are conducted, they provide a wealth of information regarding the overall trends in reactivity. However, they also generate large data sets that often require significant manual interpretation through inspection or developing case-specific analysis techniques. Here, we present an analysis method …

Rhenium Chalcogenide Clusters Containing Para-Substituted Phenylacetylide Ligands: Synthesis, Characterization, And Investigation Of Substituent Effects On Spectroscopic And Electrochemical Properties, Katherine L. Helmink, Cory A. Hicks, B. Sage Lauper-Cook, Steven J. Peters, Christopher J. A. Daley, Yann Molard, Lisa F. Szczepura

Faculty Publications – Chemistry

Four new organometallic [Re₆Se₈]²⁺-based cluster complexes containing para-substituted phenylacetylide ligands, [Re₆Se₈(PEt₃)₅(C≡C–C₆H₄–X)](SbF₆) where X = NO₂, CO₂Me, CH₃, and OMe, have been synthesized and fully characterized using ¹H, ¹³C{¹H} and ³¹P{¹H} NMR, IR, and UV–vis spectroscopy, HRMS, and elemental analysis. Three of these cluster complexes, [Re₆Se₈(PEt₃)₅(C≡C–C₆H₄–NO₂)]⁺, [Re₆Se₈(PEt …

Synthesis Of Alkyl Substituted Carbatripyrrins And Their Application To The Preparation Of Carbaporphyrins And Oxacarbaporphyrins, Ian A. Mclauchlan, Bethany K.X. Overbey, Tyler J. Smolczyk, John J. Woods, Timothy D. Lash

Faculty Publications – Chemistry

Unsubstituted carbatripyrrins have previously been shown to be useful intermediates in the synthesis of benzocarbaporphyrins and related core-modified analogues. However, the absence of substituents often resulted in the formation of poorly soluble products. In this study, four examples alkyl substituted carbatripyrrins were constructed by base-catalyzed condensation of dihydrofulvenes with pyrrole aldehydes. Further reaction with a pyrrole dialdehyde in the presence of trifluoroacetic acid afforded a series of carbaporphyrins, while reactions with 2,5-furandicarboxaldehyde generated oxacarbaporphyrins. These results demonstrate that alkyl substituted carbatripyrrins are promising precursors to new carbaporphyrinoid structures.

Assessment Of Analytical Workflows Of Gunshot Residue Evidence And Strategies For Implementation Of Advanced Technology In Crime Laboratories., Leah D. Thomas

Graduate Theses, Dissertations, and Problem Reports (ETD)

The rise in gun violence in the United States has increased the demand on forensic agencies to process evidence promptly and accurately. The exchange of imperceptible traces among objects, suspects, and victims can provide critical insights into the interactions and sequence of events during a crime. Gunshot residue (GSR) is a type of trace evidence that holds significant investigative value in shooting reconstructions. GSR can help identify potential shooters, intermediate targets, and bullet trajectories; however, its analysis is often expensive and time-consuming. Consequently, there is an urgent need for more effective solutions.

Methods for on-site screening can significantly streamline forensic …

Free Energy Approaches To Understanding The Mechanism Of Membrane-Active Peptides, Hannah R. Scott

Graduate Theses, Dissertations, and Problem Reports (ETD)

Cancer is a leading cause of death in the world today. Current methods of treatment fail to distinguish the difference between cancer cells and cells of healthy tissue, leading to off-target effects, often with terminal outcomes. A potential solution to this challenge is to target the cancer cells’ microenvironment. One universal characteristic across all cancer cells is the acidic extracellular environment. The pH-Low Insertion Peptide (pHLIP) is a membrane-active peptide with acid-sensitive function, undergoing folding and insertion into a transmembrane alpha-helix. pHLIP is a promising candidate to be used to deliver anti-cancer agents exclusively to cancer cells. Although the mechanism …

Developing Consensus-Based Methods For The Examination And Interpretation Of Contemporary Vehicle, Architectural, And Portable Electronic Device Glasses By Micro-X-Ray Fluorescence Spectrometry, Zachary Bailey Andrews

Graduate Theses, Dissertations, and Problem Reports (ETD)

Glass is a trace material that is commonly encountered during investigations of violent crimes. When glass is recovered at crime scenes, it can be used to establish links between suspects, victims, and the scene itself. The most discriminatory form of analysis for glass evidence is elemental analysis, and micro-X-ray fluorescence spectrometry (µXRF) is becoming an increasingly common technique used for this purpose. Recent advances in µXRF technology, such as the introduction of silicon drift detectors (SDD) and improved polycapillary optics are promising in enhancing the capabilities for the examination of glass evidence in forensic investigations. However, along with these advances …

Rational Design Of Small Molecules Targeting Mitochondrial Redox Proteins, Matheus Barbosa Belchior

Graduate Theses, Dissertations, and Problem Reports (ETD)

Reactive oxygen species play a crucial role in many cellular processes. Despite being a natural byproduct of cellular metabolism, overexpression of these species causes damage to the cell, leading to cell dysfunction. Central to the regulation of these highly reactive molecule is the mitochondria. Impairment in its function has been associated with oxidative stress within the cell. Herein, a ligand-based and structure-based approach to design new small molecules to inhibit mitochondrial redox proteins associated with oxidative stress and reactive oxygen species. In the first project two molecules were synthesized and characterized as potential monoamine oxidase B inhibitors. Results showed two …

Development Of Fast And Comprehensive Approaches For Gunshot Residue Interpretation Using Ambient Ionization, Mass Spectrometry, And Microparticle Sampling Studies, Thomas Dimmey Ledergerber

Graduate Theses, Dissertations, and Problem Reports (ETD)

The information derived from the forensic examination of gunshot residue (GSR) can be critical during the investigative and trial stages in the criminal justice system. However, the complexity of the GSR deposition, transfer, and persistence mechanisms calls for meticulous handling and identification processes. Novel advances in evidence interpretation and analysis via instrumental methods are current areas of growing interest that must be pushed along the chain from research to practice in a timely manner. Therefore, this research focuses on developing both rapid and comprehensive methods for detecting gunshot residue evidence and effectively communicating its significance to the investigators or trier …

3d Printed Microfluidic Platforms For Elisa-Based Diagnostics: Advancing Toward Point Of Care, Brandi Marie Binkley

Graduate Theses, Dissertations, and Problem Reports (ETD)

Protein biomarker detection is a critical analytical method for quantifying proteins in biological samples. It is relevant not only in medical diagnostics and research but also numerous other fields such as environmental monitoring, pharmacology, food safety, and biotechnology. Sensitive detection at picogram-per-milliliter (pg/mL) levels is essential for diagnosing diseases, monitoring progression, and tailoring treatments, especially for low-abundance biomarkers like troponin, interleukin 6, carcinoembryonic antigen (CEA), activin A, and vascular endothelial growth factor (VEGF). Immunoassays, particularly enzyme-linked immunosorbent assays (ELISAs), are the gold standard for protein biomarker detection due to their high specificity and sensitivity. The development of point-of-care (POC) diagnostic …

A Potentially Fruitful Path Toward A Cleaner And Safer Environment: Mxenes Uses In Environmental Remediation, Ali Mohammad Amani, Milad Abbasi, Atena Najdian, Farzaneh Mohamadpour, Seyed Reza Kasaee, Hesam Kamyab, Shreeshivadasan Chelliapan, Hanieh Ardeshiri, Lobat Tayebi, Ehsan Vafa, Sarah Mosleh-Shirazi, Alireza Jahanbin, Saravanan Rajendran, Daniel Simancas-Racines

Electrical & Computer Engineering Faculty Publications

The rapid industrialization of the world has resulted in severe environmental pollution, necessitating the development of new materials such as pollution remediation. Two-dimensional (2D) MXenes have emerged as a promising family of materials due to their unique physicochemical properties, making them ideal for environmental remediation. The article sheds light on the new opportunities of MXenes in the removal of organic and inorganic contaminants, including organic dyes, pharmaceuticals, heavy metals, radionuclides, and gas pollutants. MXenes also show excellent performance in photocatalytic degradation, adsorption, and microbial inactivation with environmental safety. Moreover, their application in recovering valuable elements from waste streams is also …

A New Paradigm For The Supramolecular Structure Of Laterally Offset Diarenes: Polymorphs Ii Of Para-Substituted Acetophenone Azines, Yp.Ph.(Me)C.N.N.C(Me).Ph.Yp (Y = Cl, Br, Ch3), Harmeet Bhoday, Kaidi Yang, Steven P. Kelley, Rainer Glaser

Chemistry Faculty Research & Creative Works

The crystal structures of polymorphs II of acetophenone azines Y_pPhRCNNCRPhY_p with R = CH₃ and Y = Cl (1M), Br (2M), and CH₃ (8M) are discussed. The azine molecules in polymorphs II are Ci-symmetric with trans-azine moieties and conrotatory phenyl twists. Polymorphs 1M-I and 2M-I contain C2-symmetric enantiomers with pronounced azine twists and disrotatory phenyl twists and allow for strong lateral double T-contacts. The three polymorphs II exemplify the new Paradigm IV for the supramolecular architectures of "laterally offset diarenes" and result in "shiplap/flat" idioteloamphiphile monolayers. Intralayer lateral attraction is provided by edge-to-face arene-arene contacts …

Electrochemically Active Molybdenum Phosphate With Open-Framework Structure, Sutapa Bhattacharya, Milad Aghayi-Anaraki, Nikolay Gerasimchuk, Steven P. Kelley, Amitava Choudhury

Chemistry Faculty Research & Creative Works

Somewhat less investigated, lithium ion containing molybdenum phosphate compounds are synthesized via simple template free hydrothermal method. Single-crystal X-ray diffraction (SCXRD) study reveals that the compounds Li_0.89Mo₂O_1.89F_0.11(PO₄)2(H₂PO₄)·xH₂O (x ≈1) and Li₃Mo₂O₂(PO₄)₃·xH₂O (x ≈1) crystallize in monoclinic C2/m and C2/c space group, respectively. The structures are built of alternate corner-sharing of MoO₆ octahedra and PO₄ tetrahedra forming layers, which are pillared by phosphate groups creating a 3D framework with channels. These …

Cold Atmospheric Plasma Induced Degradation Of Organophosphate Pesticides On Kevlar Swatches, Ta Chun Lin, Victor Somtochukwu Mbanugo, Boluwatife Stephen Ojo, Yue-Wern Huang, Marek Locmelis, Frank Daoru Han

Biological Sciences Faculty Research & Creative Works

Cold atmospheric plasma (CAP) was evaluated for degrading organophosphate pesticide (OP) residues (acephate, malathion, and dimethoate) from Kevlar fabrics. Fourier transform-Infrared (FTIR) spectroscopy, scanning electron microscope (SEM) imaging and tensile strength testing confirmed that CAP treatment preserved Kevlar's structural integrity and mechanical properties. Results show degradation efficiency increased with higher power, shorter discharge gaps, and longer exposure duration. Hyperspectral imaging supported the detection of plasma-induced spectral changes, reinforcing the presence of reactive species. The strong oxidative potential of CAP facilitated the rapid breakdown of OPs into nontoxic byproducts. These findings demonstrate the potential of CAP as a portable, energy-efficient solution …

Scope And Mechanism Of The Ruthenium-Catalyzed Sp3 C–H Coupling Reaction Of 2-Alkylindoles With Enones For The Synthesis Of Carbazole Derivatives, Krishna Prasad Gnyawali, Mina Son, Donghun Hwang, Nuwan Asanka Pannilawithana, Mu-Hyun Baik, Chase S. Yi

Chemistry Faculty Research and Publications

The catalytic system consisting of a cationic Ru–H complex 1 and 3,4,5,6-tetrachloro-1,2-benzoquinone (L1) was found to be highly effective for the dehydrative sp³ C–H coupling reaction of 2-alkyl substituted indoles with enones to form 2,4-disubstituted carbazole products. The analogous coupling reaction of 2-alkylindoles with linear enones bearing the cyclic olefinic group afforded tetracyclic carbazole products. A normal deuterium kinetic isotope effect was measured from the coupling reaction of 1,2-dimethylindole versus 1-methyl-2-(methyl-d₃)indole with (E)-3-penten-2-one (k_H/k_D = 2.5). The Hammett plot was constructed from the reaction of para-substituted …