“Every day I am reminded of the enormous opportunity I have been blessed with at Trinity Western University: that I, as an undergraduate student, can be thoroughly involved in influential scientific research. Being a part of the Friesen Research Group here at TWU opened my eyes to the true intricacy and beauty of chemistry and taught me more than any chemistry class or lab could have.”
– Alan Brooke, (BSc Chemistry, 2022)
The most reactive element on the periodic table is fluorine. In nature, fluorine is not found existing freely on its own until recently. To isolate fluorine, a chemist must synthetically separate it from other compounds. Early chemists in history have been injured, blinded or killed in their experiments to isolate fluorine.
In 1906, French chemist Henri Moissan was awarded the Nobel Prize for successfully isolating fluorine in 1886 — a success he achieved only after surviving several poisonings from prior attempts. Without the fearless efforts by former fluorine chemists, the world would not have anesthetics for surgery or some of the best performing pharmeceutical drugs. Additionally, 40 per cent of our agrochemicals to improve crop yield would not exist, neither would there be PET imaging for monitoring cancer, nuclear power, flat screen TVs, electronics, Gortex® rain jackets, long operating satellites, rockets, or aircraft. These are only some of flourine’s common applications.
Here at Trinity Western University, the Friesen Research Group led by Dr. Chadron M. Friesen with 24 years of experience, works to safely incorporate the element, fluorine, into molecules within a specialized lab on campus.
Working with a unique and reactive element
Alan Brooke is an undergraduate student at TWU who is majoring in Chemistry with a focus on the “Life-Sciences” stream, and minoring in general Biology. He plans on graduating in Spring 2022.
This summer, Brooke received an award from the Natural Sciences and Engineering Research Council of Canada (NSERC USRA). The project he is currently working on, titled, “Small Molecule Fluorine Chemistry,” extends from work he accomplished last summer under a TWU summer award.
“Fluorine is quite a unique element in chemistry,” Brooke explains, “unlike elements such as carbon, nitrogen, and oxygen which we might hear about on a daily basis.”
“There are only a handful of fluorine-containing natural products mainly found in plants in Africa, meaning that if a chemist wants to incorporate fluorine in a specific molecule, they must do so synthetically.”
Alan Brooke, BSc Chemistry, 2022
Applications in top-performing drugs
Fluorine, when combined with other elements, has many useful, everyday applications. When fluorine is added to city water supplies in very low concentrations, it is known to help prevent tooth decay.
A good example of a synthetic fluorine-containing material is Teflon®, the invention that has resulted in non-stick cooking pans.
Perhaps one of fluorine’s most significant roles is within medicine.
Approximately 25 percent of pharmaceuticals, including those for cancer, the central nervous system, and the cardiovascular system, contain some form of fluorine. Fluorine is found within the chemical structures of approximately 33 per cent of the top-performing drugs, Brooke reports.
Over many years, scientists have found that the addition of just a single fluorine atom to various compounds can greatly enhance their lipophilicity (which influences drug absorption), metabolic stability and biological activity as a drug, says Brooke.
How TWU research advances the field of science
Brooke’s project includes developing new strategies for introducing fluorine into organic molecules (organic meaning that the molecule mainly consists of carbon).
“As a part of the Friesen Research Group at TWU, my goal was to figure out if I could ‘fluorinate’ (introduce fluorine into) specific sulfur-containing organic molecules, practically replacing the sulfur with fluorine.”
“There has been precedent for this type of chemistry especially from our very own researchers at TWU,” Brooke shares.
A peer-reviewed journal article authored by Josiah Newton (a PhD student researching with Dr. Friesen) was published in 2019 describing the mild synthesis of ‘difluoro-ethers’ using silver(I) fluoride (AgF).
Developing cleaner, safer methods to synthesize molecules
“During my time researching at TWU last summer I developed and optimized a novel reaction which incorporates the use of AgF in the synthesis of ‘difluoro-benzodioxoles,’” says Brooke. “This specific class of organic compounds is found within pharmaceuticals, agrochemicals, and organic materials.”
The discovery of this novel reaction was significant because all other existing methods to synthesize difluoro-benzodioxoles involve the use of harsh and toxic chemical reagents. The method that Brooke discovered, however, is relatively easy to use and is harmless to a child.
“I altered a number of reaction variables to the point that I could consistently synthesize various difluoro-benzodioxoles, each with different modifications to their chemical structure,” says Brooke. Difluoro-benzodioxles, for example, have a role in helping people with cystic fibrosis to monitor neuropathic pain or inhibit immunosuppression. In additon, it has also shown anti-parasitic activity.
First prize winner at international conference
In November 2019, Brooke presented his research at the 28th Annual Murdock College Science Research (MCSR) Conference and took home first prize for the top research poster in the organic chemistry section.
Brooke won first prize for the top research poster in the organic chemistry section at the 28th Annual Murdock College Science Research (MCSR) Conference.
“The M.J. Murdock Charitable Trust who host the MSCR Conference each year has supported TWU research through generous grants for many years now,” says Brooke, “I was very happy that I could represent Trinity Western University at a conference of mostly American schools, demonstrating that our TWU research is indeed influential and important.”
“The novelty of the chemistry, its potential influence on the synthesis of pharmaceuticals, and its practicality in comparison to existing methods are the reasons why we were compelled to compile our data in a journal article which summarizes our findings and results,” he says.
The article that Brooke has helped to write has just been accepted into the ACS Journal of Organic Chemistry.
COVID-19 and summer research at TWU
Brooke admits that being an undergraduate researcher at TWU this summer has had its trials. The COVID-19 lockdowns began right before lab research would have begun in May.
“Due to the strict rules surrounding social distancing, the start to my research this summer consisted of many hours of literature review and reading up on what other chemists have contributed in the field of organic chemistry,” says Brooke.
Later, Brooke received good news. “Just about 10 weeks into my research, I was thrilled to hear that our application to be allowed to work in the lab had been accepted – with COVID-19 safety measures in place, of course.”
By then, Brooke was ready to be back. “Part of my research-from-home period was spent planning various experiments I was curious to try, so I got right to those during my first week back in lab,” he says.
“With the difluoro-benzodioxole project all wrapped up, I have been working on developing a whole new fluorination method which does not depend on the use of AgF but instead uses novel chemical reagents to synthesize pharmaceutically relevant organic compounds using even cheaper metals than silver,” Brooke reports.
Producing influential scientific research at TWU
Not all experiments are successful, and Brooke shares how he learns from each outcome.
“In my day-to-day research in the lab there are plenty of failed reactions, but these are just as important and informative as the exciting successful reactions that occur. Every result adds a new piece to the puzzle in terms of solving a problem, reaching a goal, and in my case, synthesizing molecules,” he says.
Brooke is grateful for his work as a chemist. “Every day I am reminded of the enormous opportunity I have been blessed with at Trinity Western University, that I, as an undergraduate student, can be thoroughly involved in influential scientific research,” he says.
“Being a part of the Friesen Research Group here at TWU opened my eyes to the true intricacy and beauty of chemistry and taught me more than any chemistry class or lab could have. I am extremely grateful for my position at TWU and glad that I get to be surrounded by things that I am so passionate about in my summer workplace.”