Chemistry @ Dal
Dalhousie University

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THOMPSON GROUP RESEARCH

Dr. Alison Thompson, Faculty of Science Killam Professor of Chemistry
Education: B.Sc. Hons I; I was an undergraduate at the University of Leicester in the UK (long before Leicester City won the Premier League); I gained my Ph.D. at the University of Sheffield in the UK with Dr. Varinder Aggawal; PDF in Strasbourg (Prof. Solladie-Cavallo) in France, and then UBC (Dr. David Dolphin) in Vancouver.

Research: In my Ph.D. I learned that if the product wasn't white and wasn't crystalline then it couldn't possibly be pure; this limited knowledge was turned on its head when I started working with polypyrroles - stunning oranges, purples, reds, and sometimes even black. My research group develops synthetic methodology to make new types of functional pyrroles and polypyrroles in elegant ways; we complex many of our polypyrroles and investigate their optical properties or bioactivity. We have many hundreds of pyrroles in our lab, but there is always the need for a few more.

Publications: Our publications link has my full record.

Fun Facts: I have two children; we have a dog; I ride my bike to work; I swim a lot; I enjoy making things from yarn or anything else that inspires - my current project is a crocheted blanket that resembles the landscape of a farm (brown ridges for a ploughed field, yellow corn field, blended green and yellow hay field, red for the barn; you get the idea).

Michael Beh, PhD Student
Education: HBSc Chemistry: I was an undergraduate at Lakehead University in Thunder Bay, ON.

Research: I began working with dipyrrins, specifically F-BODIPY dyes. F-BODIPY compounds are brilliantly coloured both in solution and as solids, quite a sight what I was familiar with in organic chemistry. I started looking at the synthesis of these compounds and how sensitive they were to non-anhydrous conditions. I have since finished that project and moved on to two others dealing more with monopyrroles. One project is working towards building sulfur-bridged dipyrroles with the goal of synthesizing a sulfur-bridged tetrapyrrole. The other project focuses on a group of specifically substituted monopyrroles and the mechanism behind their formation.

Awards: NSHRF Scotia Support Grant, MSc Nova Scotia Graduate Scholarship, Douglas E. Ryan Prize

Recent Conference Presentation: Robust Synthesis of FBODIPYs Beh, M.H.R.; Douglas, K.I.B.; House, K.T.E.; Murphy, A.C.; Sinclair, J.S.T.; Thomspon, A. 100th Canadian Chemistry Conference and Exhibition, May 2017, Toronto, ON.

Publication:
Robust Synthesis of F-BODIPYs. Michael Helmut Reynolds Beh, Katherine Isabelle Biehn Douglas, Kelsey Taylor Elver House, Alexandra Celeste Murphy, Jackson Scott Testemale Sinclair and Alison Thompson*. Org. Biomol. Chem. 2016, in press, OB-ART-10-2016-002238.R1.

Recent Conference Poster:
Mechanistic Studies in the Synthesis of Symmetrical Dipyrrins. Beh, M.H.R.; Lund, K.A.R.; Kajetanowicz, A.; Thompson, A. 99th Canadian Chemistry Conference and Exhibition, June 2016, Halifax, NS.

Fun Facts: I'm a big fan of games, movies, and TV shows. I'm a big fan of hiking, canoeing, and camping. I bike to school everyday. Dogs are the best thing ever and cats are OK too I guess.

  Sarah Davies (Greening), PhD Student
Education: B.Sc. Chemistry; I was an undergraduate at the University of Central Florida (Dr. Howard Miles) and currently pursing graduate work with Dr. Alison Thompson, at Dalhousie University.

Research: At the University of Central Florida, I worked with the natural product, podocarpic acid. The work involved copper-catalyzed cross coupling reactions with thiols to develop novel compounds with potential as new drug leads. In the Thompson group, current work involves F-BODIPY synthesis and study of the photophysical properties of prodigiosenes, a synthetic analog to the natural, biologically active product, prodigiosin.

Awards: Anna Wilson Scholarship, Dalhousie President's Graduate Teaching Assistant Award

Recent Conference Presentation: 8th MNPC 2016 (Halifax, Canada). "Prodigiosene F-BODIPYs: Synthesis and Characterization"

Publications
Asymmetric diapyrrin and F-BODIPYs conjugated to terminal alkynes and alkenes. Figliola, C.; Robertson, K.; Greening, S; Thompson, A. J. Org. Chem., 2017

Recent Conference Posters:
Prodigiosene F-BODIPYs: Synthesis and Characterization. Greening, S.; Thompson, A. 100th Canadian Chemistry Conference and Exhibition, May 2017, Toronto, ON.

Prodigiosene F-BODIPYs: Synthesis and Characterization. Davies, S.; Thompson, A. BHCRI/TFRI Cancer Research Conference in Atlantic Canada, November 2016, Halifax, NS.

Prodigiosene: A Synthetic Natural Product with Significant Biological Activity and Potential as a Molecular Probe. Greening, S.; Thompson, A. 99th Canadian Chemistry Conference and Exhibition, June 2016, Halifax, NS.

Synthesis, Characterization & Photophysical Properties of Prodigiosene F-BODIPYs. Greening, S.; Thompson, A. 41st Annual Science Atlantic/CIC Student Chemistry Conference, June 2016, Halifax, NS.

Fun Facts: I love animals, reading & coloring. I currently have 3 cats & 2 dogs; my favorite author is Terry Goodkind; and I have to resist the urge to buy a new adult coloring book every time I see one in a shop. I also enjoy the sun (having lived many years in Florida) and board games.



Roberto Diaz-Rodriquez, Honours Undergraduate Student
Education: Entering my fourth year of a B.Sc. Honors in Chemistry at Dalhousie University.

Research: Currently investigating methodologies for attaching functional groups to the boron of aza-BODIPYs.

Awards: IB Renewable Scholarship

Fun Facts: Music is one of my great passions; I am a big fan of progressive metal, play a couple of instruments and enjoy making effects pedals for electric instruments in my free time. Bit of a geek and a huge League of Legends fan, and also love cycling.


  Luke Burke, Honors Undergraduate Student 
Education: I am going into my fourth year of a B.Sc (Honours in Chemistry) at Dalhousie University.

Research: My previous undergraduate research involved low temperature production of graphite as an anode material for Lithium ion batteries, and my current research is focused on a novel synthesis route for the production of symmetrical and non-symmetrical aza-dipyrrins.

Publication:
M.N. Obrovac, Xiuyun Zhao, L.T. Burke, R.A. Dunlap, Reversible Lithium Insertion in Catalytically Graphitized Sugar Carbon, Electrochem. Commun., 60 (2015), 221-224.

Awards: NSERC USRA 2015, 2016, Kenneth and Dorothy Hayes Memorial Prize and Norbert Wolter Memorial Scholarship

Fun Facts: I enjoy playing hockey and tennis, as well as taking my dog to the lake and lounging on the beach.

 
Min Kim, Honors Undergraduate Student 
Education
: I am going into fourth year (undergraduate) at Dalhousie University.

Research: Last year (summer of 2015), my project involved probing different reduction methods that could transform pyrrole aldehydes into amides. Also, I learned how to make pyrroles with different functional groups such as aldehydes, esters, and amides. Currently, I am working on the synthesis of various dipyrrins and BODIPYs from simple pyrroles.

Awards: Laing's Award, Faye Sobey Award, Canadian Society for Chemistry Silver Medal and Norbert Wolter Memorial Scholarship

Fun Facts: I play piano and enjoy watching The Voice!

Brandon Groves, PhD Student

Education: Dalhousie University: Ph.D. Organic Chemistry (Expected graduation, 2017), Thesis Title: "The Synthesis of Prodigiosene-Based Anticancer Reagents and Development of Reactions for Dipyrrin-Based Molecules"; St. Francis Xavier University: B. Sc. Chemistry with First Class Honours (2011), Thesis Title: "Exploration of Chiral Induction in Tetrabenzoate Diruthenium(II,III) Complexes via Chiral Diphosphine Ligands"

Research: My current research interests are broad, and are best described as focused on the chemistry of pyrrole and its extended frameworks (prodigiosenes, dipyrrins and F-BODIPYs). My most recently finalized projects include decarboxylative coupling of mono-pyrroles, manipulation of alpha-methyl substituted dipyrrins, and the synthesis of F-BODIPYs via use of Lawesson's reagent from mono-pyrrolic starting materials. My long-term goals involve training in the field of medicinal chemistry, with the goal of pursuing a career in pharmaceutical development.

Publications
Highly-substituted N-protected pyrroles under Pd-catalysed decarboxylative cross-coupling. Figliola, C; Groves, B. R.; Thompson, A. In Progress.

Reactivity of the 1-methyl functionality of dipyrrins. Groves, B. R; Thompson A. In Progress.

Synthesis and evaluation of folate-conjugated prodigiosenes. Figliola, C.; Marchal, E.; Groves, B. R.; Savoie, H.; Boyle R. W.; Thompson, A. Submitted to Bioconjugate Chem., April 2016.

Thionation reactions of 2-pyrrole carboxylates. Groves, B. R.; Smithen, D. A.; Cameron, T. S.; Thompson, A. RSC Adv., 2016, 6, 69691.

Recent Conference Presentation:
1. Groves, B. R.; Smithen, D. A. Cameron, T.S.; Thompson, A. "Thionation of a-Ester Pyrroles and Application in the Synthesis of F-BODIPYs." 99th Canadian Chemistry Conference and Exhibition, 2016, Oral Presentation.

2. Groves, B. R.; Thompson, A. "Functionalization of a-Methyl Substituted Dipyrrins." 98th Canadian Chemistry Conference and Exhibition, 2015, Poster Presentation.

Synthesis and Applications of Dipyrrins
Brandon's Papers, Conference Posters and Presentations

Awards:
Bruce and Dorothy Rossetti Traineeship in Cancer Research: Beatrice Hunter Cancer Research Institute, September 2017 - September 2019 ($36,750 per annum).

Postgraduate Scholarship: NSERC, May 2014 - April 2017 ($17,500 per annum).

Level 2 Izaak Walton Killam Predoctoral Scholarship: Killam Trusts, September 2013 - September 2017 ($25,000 per annum).


Fun Facts: In my spare time, I enjoy playing tennis with my wife and-old step-daughter, as well as playing pick-up hockey as frequently as possible.
Travis Lundrigan, PhD Student

Synthesis and Applications of Dipyrrins
Travis's Papers, Conference Posters and Presentations