Dobbin Atlantic Scholar Report: Synthesis of Bicyclo[1.1.1]pentane Appended Porphyrins by Michael Beh

July 25, 2018

Dobbin Atlantic Scholarship Report by Michael Beh

Home university: Dalhousie University, Halifax, Nova Scotia, Canada; working under Prof.
Alison Thompson

Host university: Trinity College, Dublin, Ireland; working under Prof. Mathias O. Senge

Title of research: Synthesis of Bicyclo[1.1.1]pentane Appended Porphyrins

Description of academic field: chemistry, synthetic organic chemistry, tetrapyrroles, porphyrins

I am a PhD candidate at Dalhousie University in Halifax, and my research focuses on the synthesis and study of pyrrolic frameworks for applications in biosciences. I was awarded a Dobbin Atlantic Scholarship for a five-week research trip to Trinity College in Dublin in May/June 2018. During my time at Trinity I was hosted in the Chemistry Department by Prof. Mathias O. Senge, a Science Foundation Ireland (SFI) Research Professor, and the acting Chair of Organic Chemistry.

Prof. Senge runs the SFI Tetrapyrrole Laboratory, a world leader in porphyrin research.  Prof. Senge’s research focuses on the development of new methods for the synthesis of a wide variety of porphyrin compounds and their physical, structural, and biological characterisation.  The research is geared towards both leaps in the understanding of porphyrins’ fundamental chemistries, and their devolvement into useful materials for society in a wide diversity of applications.

In the first two weeks of my stay I familiarized myself with the new research laboratory, new synthetic procedures, and of course the city of Dublin. Having lived primarily in smaller cities, staying in Dublin city centre was a unique and interesting adventure that I was happy to take on. During my time at Trinity I focused on the synthesis of bicyclo[1.1.1]pentane (BCP) and porphyrin compounds. Despite the very difficult synthetic challenges of porphyrin synthesis, these types of compounds are highly-coloured and were an absolute pleasure to be able to work with.


A variety of porphyrin compounds showing off their intense colours

While working in the SFI Tetrapyrrole Laboratory at Trinity, I brought along an already strong background in organic synthetic chemistry, and as a result I was able to quickly learn the basics to synthesize porphyrin and BCP compounds and started to pick-up the intricacies associated with them as two famously challenging fields among synthetic chemists. It often takes weeks to prepare even just tens of milligrams of these types of compounds. Imagine a teaspoon of sugar in your morning coffee, which is roughly 4 grams, and the scale of porphyrin syntheses is often 100-1000 times smaller! In the following three weeks I continued working with BCP and porphyrin compounds, successfully preparing two entirely new BCP compounds. I was able to take these new compounds and, working with 15-20 milligrams, successfully couple them to a variety of different porphyrins to make now four entirely new BCP-containing porphyrin compounds.

The work done and the contributions I made while at Trinity has built on the foundation for a larger, and still continuing project exploring the physical, chemical, and structural properties of these new BCP-containing porphyrin compounds, and exploring the synthesis of more, similarly structured porphyrin compounds and their properties, as well. My contributions during this time will lead to a collaborative scientific journal article between both Prof. Senge’s and Prof. Alison Thompson’s (my PhD supervisor) research groups. Our two research groups will be able to build upon my trip to establish more collaborative efforts in the future, creating a stronger link between our research, and between Trinity College and Dalhousie University.

The research I did at Trinity parallels my on-going PhD research, but has largely different points of focus. Working in a field similar to my own has given me an entirely new approach and has been an incredible experience, helping to widen my scope of knowledge and is sure to help in my future studies and careers. I was given the chance to work alongside many incredible scientists, all of whom were welcoming, allowed me to be a part of their team, and made my time at Trinity, and in Ireland, so much more enjoyable. I am incredibly thankful and appreciative of all the help I’ve received and to everyone involved in making this experience possible.