Research opportunities create windows for learning and excelling
James Cox enjoys chemistry, and his natural instincts, curiosity, hard work, and dedication are a perfect combination to spiral him into an outstanding scholar, researcher, and student.
James is a senior, award-winning chemistry major, conducting research with Professor Joseph Topczewski in the Department of Chemistry. He is a University honors student, received the Department of Chemistry’s 2018 Robert C. Brasted Memorial Fellowship, and was named 2018 Goldwater Scholar.
For James, his love for science began when he studied chemistry as an eighth grader through online courses. As a senior in high school, he was awarded a silver medal in the Science Olympiad. In the spring of his freshman year at the University, James kick-started his undergraduate research by joining Professor Topczewski’s lab.
Allylic azide rearrangement
His first major research project dealt with the effect of neighboring groups on allylic azide rearrangement. At room temperature, allylic azides undergo rearrangement to a variety of equilibrating isomeric compounds. The research goal was to understand how the functional groups around the allylic azide influenced the ratio between the various isomers at equilibrium. James helped synthesize eight allylic azide-containing substrates and studied their isomer ratios using proton nuclear magnetic resonance spectroscopy. All of those substrates could be prepared from commercially available starting material in two to three steps. James’ partners in this research were graduate student Mary Packard and undergraduate Victoria Suding who graduated in the spring of 2017.
From this research, James gained a lot of experience working with air-sensitive reactions and column chromatography purification. “I barely go a day in lab now without using one of these techniques; they are truly indispensable in the organic research lab,” he said.
This research led to James being second author on an article that appeared in the European Journal of Organic Chemistry in 2017. The research was also featured on the journal’s cover. He was heavily involved in proofreading the article, meticulously reviewing each spectrum for each compound involved in the project, ensuring that every peak could be rationalized by the compound’s structure, checking for any impurities, and contributing ideas for the design of the cover art.
James said that he valued the experience of seeing a project from its infancy to the pages of an international chemistry research journal. “I gained perspective on what being an academic chemist entails and what my future as a graduate student, post-doctoral scholar and, hopefully, professor will involve,” he said.
Synthesizing new Porsche red
For the past year, James’ focus in the lab has encompassed synthesizing an oxygen-18 labeled analog of perylenetetracarboxylic dianhydride (PTCDA), the dye responsible for the red color of many sports cars, which is sometimes known as Porsche red.
While PTCDA without the oxygen-18 label is cheap and commercially available, the addition of the oxygen-18 makes a compound that has never been synthesized before. Additionally, labeled PTCDA is challenging to synthesize in the lab. Oxygen-18 is also expensive. Essentially, James has to synthesize intermediates that will be soluble enough in organic solvents to undergo reactions, while installing the oxygen-18 late in the synthesis to avoid losing it in subsequent reactions.
Initial trial, error, and failure now appear to be leading to success. James investigated a synthetic route that eventually failed because of the insoluble intermediates. Knowing that solubility was a key issue with these compounds, Professor Topczewski and James revised the order of the steps for the original synthesis. Their hypothesis: by performing one of the two required coupling events, and leaving the second until the end of the synthesis, the intermediates should be more soluble. Success: using this approach, it appears that the researchers have solved the solubility-related reactivity issues.
James is an independent researcher on this project, solely responsible for carrying out all of the experiments, reading the relevant literature on the reactions, interpreting the data, and maintaining a steady rate of progress.
“I recognize that this is a unique experience to have as an undergraduate. It has definitely taught me a lot about time management and thinking critically as a researcher,” said James.
“James is an extremely talented student and researcher,” said Professor Topczewski. “He has a bright future moving forward, and I can’t wait to see what he does in graduate school.”
During the summers, James gained additional hands-on, cutting-edge research experience as a Heisig/Gleysteen research fellow in the Department of Chemistry in 2017, and as an Amgen Scholar at the California Institute of Technology in 2018. At Caltech, he worked with Professor Robert Grubbs, a 2005 Nobel Laureate in Chemistry, on developing a new method to make aromatic 1,2-dithiols via aryne intermediates. Aromatic 1,2-dithiols are commonly found as ligands on olefin metathesis catalysts that the Grubbs lab has been developing since the 1980s. James’ method using aryne intermediates is supposed to be more efficient and tolerant to reactive molecules. While he was able to show that this new method is viable, he was not able to isolate pure dithiol product: additional optimization is needed to develop it into a practical synthesis.
“Perhaps the most valuable lesson I learned was about the importance of forming connections within the chemistry community,” said James. “I had the privilege of meeting chemistry professors, post-doctorates, graduate students, and undergraduates from Caltech and Stanford who provided in-depth advice about graduate school, critiqued my presentations and reports, and taught me new lab techniques. Many of the other visiting scholars with whom I worked and lived are also applying for graduate school this fall, so I will likely run into some of them later in my career.
“I feel much better connected within my field because of my time at Caltech,” James said. “Additionally, through this experience, I learned what it is like to adjust to a completely new research environment: new lab space, new equipment, new people, new facilities, etc. As a result, my summer was almost identical to the first few weeks of graduate school. Looking ahead to the start of my graduate school tenure next fall, I am reassured knowing that I can handle such an adjustment.”
In addition to his studies and research, James is also an involved student, serving as president of the oSTEM student group, a national society dedicated to educating and fostering leadership for lesbian, gay, bisexual, transgender, queer, intersex, and asexual (LGBTQIA+) communities in the science, technology, education, and math (STEM) fields, and on the Department of Chemistry’s Diversity & Inclusion Committee.
“All of science benefits from being inclusive of diverse people,” said James. “An accepting department sends a powerful message to its members and the community that everyone in it is free to be true to themselves, that they have no need to hide any part of their identity in the workplace. As a result, people in diverse, inclusive departments do not spend much of their energy worrying if they will be accepted by their peers and, instead, can focus on their work. Additionally, prospective students and faculty feel welcomed by seeing people who look, love, or identify like they do. So, an inclusive department looses fewer people who would have valuable ideas to contribute. Essentially, I take a very pragmatic approach to diversity and inclusion work: I believe people will be able to do their best work in a diverse environment.”
All of these accomplishments and the awards and experiences that accompanied them were sought out by James. He learned a lot in the process, including:
- Stepping outside of his comfort zones as often as possible. “I secured my research position early on as an undergraduate because I put myself out there and asked for it,” said James. “I consistently think this was one of the best decisions I have made.”
- Learning how to think scientifically by becoming involved in research. “In academic research, there are very few procedures to follow or guiding worksheets as lifelines, there are just questions,” said James. “The job of the researcher is to intuit ways to answer these questions and get them answered. An ability to apply chemistry knowledge to unfamiliar, abstract problems is key to successful research. This intellectual freedom and application of knowledge is unique to research, but so important to any budding scientist.”
- Applying for everything, possibly earning awards and scholarships. “You will earn some of the scholarships and fellowships that you apply for, but absolutely none, if you don’t,” said James
- Valuing your mental health as if it were your physical health.
- Asking questions. “In chemistry, failing to ask an important question could realistically end up causing a serious accident in lab,” said James. “No matter how big or small, insightful or stupid, questions are worth asking.”
James graduates in the spring of 2019. As for the future, he plans to complete a doctorate in organic chemistry and conduct research to improve synthetic strategies.