Gwendolyn Anne Bailey

Department of Chemistry Tel: (613) 562-5800 ext. 6067 University of Email: [email protected] Ottawa, ON, K1N 6N5

EDUCATION Ph.D. University of Ottawa (Ottawa, ON); 2012–present Specialization in Transition Metal Catalysis. Advisor: Prof. Deryn Fogg Thesis: Overcoming Catalyst Decomposition in Olefin Metathesis: Challenges, Insights, Opportunities B.Sc. University of (, BC); 2008–2012 Honours in Chemistry, with Distinction; Co-op. Advisor: Prof. Chris Orvig Thesis: A Novel Acyclic Chelator for Radiopharmaceutical Applications (Lefevre Medal & Prize in Honours Chemistry) Transfer College of the Rockies (Cranbrook, BC); 2006–2008

HONOURS AND DISTINCTIONS Scholarships 2014–17 NSERC Canada Graduate Scholarship, Doctorate (CGS-D) $35,000 p.a. 2013–17 Excellence Scholarship, University of Ottawa $7,500 p.a. 2013–14 NSERC Canada Graduate Scholarship, Master’s (CGS-M) $17,500 2013–14 Graduate Scholarship (declined) $15,000 2012–13 Admissions Scholarship, University of Ottawa $7,500 p.a. 2012 UBC Conference Travel Award $800 2011 NSERC USRA, Medicinal Inorganic Chemistry Group, UBC $6,000 2010 NSERC USRA (x2), Tekmira Pharmaceuticals Corp. $12,000 2008–12 Trussell Science and Technology Scholarship $5,000 p.a. 2008–10 Chancellor’s Entrance Scholarship, UBC $5,000 p.a. 2008 Irving K. Barber British Columbia Transfer Scholarship $5,000 2008 Irving K. Barber One World Scholarship $2,000 2008 Nancy Ryckman Scholarship, UBC $1,600 2008 Faculty Association Scholarship, College of the Rockies $2,000 2006–08 Scholastic Distinction Scholarship, College of the Rockies $3,500 p.a. 2005 Cranbrook Rotary Club Scholarship $1,000

Awards 2017 Featured as an “Outstanding Student” in the University of Ottawa Annual Research Report - 2017 Registration Award for selected lecture (1 of 3 graduate student lectures); Gordon Research $650 Conference on Inorganic Reaction Mechanisms 2017 Registration Award for selected lecture (1 of 8 graduate student lectures); Gordon Research $350 Seminar on Inorganic Reaction Mechanisms 2016 Teaching Assistant of the Year Award (CHM/BCH); Faculty of Science, uOttawa $250 2016 Teaching Assistant Award; Chemistry and Biomolecular Sciences, uOttawa $100 2016 Oral Presentation Award; 24th Canadian Symposium on Catalysis $100 2015 Oral Presentation Award (2nd prize); 48th Inorganic Discussion Weekend book 2014 Teaching Assistant of the Year Award; Faculty of Science, University of Ottawa $250 2014 Teaching Assistant Award; Department of Chemistry, University of Ottawa $100 2012 Oral Presentation (1st prize, organic division); Western Canadian Undergrad. Chemistry Conf. $100 2012 Lefevre Medal & Prize in Honours Chemistry, UBC (highest academic standing; research thesis) $300 2005 Governor General Academic Bronze Medal, Mount Baker Secondary School (highest standing) medal 2005 Apollo Ristorante Top Music Student Award, Mount Baker Secondary School $100 Total funds awarded (CAD): $246,950

Gwendolyn Anne Bailey

PUBLICATIONS (F = full article; C = communication; R = review; †equal contributions) 13C. Bailey, G.A.; Fogg, D.E. Understanding Initiation and Recapture of Olefin Metathesis Catalysts: A Classification Scheme. (In preparation) 12R. Bailey, G.A.; Nascimento, D.L.; Fogg, D.E. Decomposition of Highly-Active Ruthenium Olefin Metathesis. Acc. Chem. Res. (Invited review; due Dec. 20) 11C. Bailey, G.A.; Lummiss, J. A.; Foscato, M.; Occhipinti, G.; McDonald, R.; Jensen, V.R.; Fogg, D.E. Decomposition of Metathesis Catalysts by Brønsted Base: Evidence for Metallacyclobutane Deprotonation as a Primary Deactivating Event. J. Am. Chem. Soc. 2017. (Accepted pending minor revision) 10C. Bailey, G.A.; Higman, C.S.; Day, C.S.; Fogg, D.E. Bimolecular Coupling as a Vector for Decomposition of Fast- Initiating Metathesis Catalysts. 2017. (Revised version submitted Sept. 30; J. Am. Chem. Soc.) 9C. Higman, C.S.; do Nascimento, D.L.; Ireland, B.J.; Audörsch, S.; Bailey, G.A.; McDonald, R.; Fogg, D.E. Chelate- Assisted Ring-Closing Metathesis: A Strategy for Accelerated Macrocyclization at Ambient Temperatures. J. Am. Chem. Soc. 2017. (Under revision) 8F. Santos, A.G.†; Bailey, G.A.†; dos Santos, E.N.; Fogg, D.E. Overcoming Catalyst Decomposition in Acrylate Metathesis: Polyphenol Resins as Enabling Agents for PCy3-Stabilized Metathesis Catalysts. ACS Catal. 2017, 7, 3181–3189. (ACS Editor’s Choice; also selected for ACS virtual issue on “Hot Materials in a Cool Country”) 7F. Bailey, G.A.; Fogg, D.E. Confronting Neutrality: Maximizing Success in the Analysis of Transition-Metal Catalysts by MALDI Mass Spectrometry. ACS Catal. 2016, 6, 4962–4971. 6C. Bailey, G.A.; Fogg, D.E. Acrylate Metathesis via the Second-Generation Grubbs Catalyst: Unexpected Pathways Enabled via a PCy3-Generated Enolate. J. Am. Chem. Soc. 2015, 107, 7318–7321. 5F. Rodríguez-Rodríguez, C.; Telpoukhovskaia, M.A.; Alí-Torres, J.; Rodríguez-Santiago, L.; Manso, Y.; Bailey, G.A.; Hidalgo, J.; Sodupe, M.; Orvig, C. Thioflavin-Based Molecular Probes for Application in Alzheimer’s Disease: From in Silico to in Vitro models. Metallomics 2015, 78–87. 4F. Telpoukhovskaia, M. A.; Rodríguez-Rodríguez, C.; Cawthray, J. F.; Scott, L. E.; Page, B. D. G.; Alí-Torres, J.; Sodupe, M.; Bailey, G.A.; Patrick, B.O.; Orvig, C. 3-Hydroxy-4-pyridinone Derivatives as Metal Ion and Amyloid Binding Agents. Metallomics 2014, 6, 249–262. 3F. Bates, J.M.; Lummiss, J.A..; Bailey, G.A.; Fogg, D.E. The Boomerang Mechanism in Olefin Metathesis Reactions Promoted by the Second-Generation Hoveyda Catalyst. ACS Catal. 2014, 4, 2387–2394. 2F. Bailey, G.A.†; Price, E.W.†; Zeglis, B.M.; Ferreira, C.L.; Boros, E.; Lacasse, M.J.; Patrick, B.O.; Lewis, J.S.; Adam, M.J.; Orvig, C. A Versatile Multifunctional Chelator for 67Ga, 64Cu, 111In, and 177Lu. Inorg. Chem. 2012, 51, 12575–12589. 1F. Price, E.W.; Cawthray, J.C.; Bailey, G.A.; Ferreira, C.L; Boros, E.; Adam, M.J.; Orvig, C. H4octapa: An Acyclic Chelator for 111In Radiopharmaceuticals. J. Am. Chem. Soc. 2012, 134, 8670–8683.

SCHOLARLY PRESENTATIONS (O = oral; P = poster; *indicates presenter) O18. Bailey, G.A.*; Higman, C.S.; Fogg, D.E. Catalyst Decomposition in Ru-Catalyzed Olefin Metathesis: Insights Originating in a Cyclometallated Ru Dimer. Student symposium for 2017 Leibniz prize winner, Prof. Holger Braunschweig, Ottawa: May 2, 2017. (Institutional) O17. Bailey, G.A.*; Higman, C.S.; Fogg, D.E. Catalyst Decomposition in Ru-Catalyzed Olefin Metathesis. Poster talk presented at the Gordon Research Conference in Inorganic Reaction Mechanisms, Galveston, TX: Mar 5– 10, 2017. (International; Short talk selected from poster abstracts) P16. Bailey, G.A.*; Higman, C.S.; Fogg, D.E. Metallacyclobutane Deprotonation as a Primary Event in Decomposition of Olefin Metathesis Catalysts. Gordon Research Conference in Inorganic Reaction Mechanisms, Galveston, TX: Mar 5–10, 2017. (International) O15. Bailey, G.A.*; Higman, C.S.; Fogg, D.E. Understanding Catalyst Decomposition in Olefin Metathesis. Gordon Research Seminar in Inorganic Reaction Mechanisms, Galveston, TX: Mar 4–5, 2017. (International; Selected) O14. Bailey, G.A.*; Higman, C.S.; Fogg, D.E. Metathesis of Directly Functionalized Olefins: Probing Decomposition of Electron-Deficient Intermediates. Centre for Catalysis Research & Innovation lunchtime seminars, Ottawa, ON: Dec 8, 2016. (Institutional) P13. Bailey, G.A.*; Fogg, D.E. Analyzing Transition-Metal Complexes by MALDI MS: Maximizing Success. Gordon Research Conference in Inorganic Chemistry, Biddeford, ME: June 19–24, 2016. (International) Gwendolyn Anne Bailey

O12. Bailey, G.A.*; Fogg, D.E. Frontiers in Metathesis: Electron-Deficient Olefins. Ottawa-Carleton Chemistry Institute Meeting, Ottawa, ON: June 3, 2016. (Institutional) O11. Bailey, G.A.*; Fogg, D.E. Frontiers in Metathesis: Electron-Deficient Olefins. 24th Canadian Symposium on Catalysis, Ottawa, ON: May 8–11, 2016. (National; Oral Presentation Award) P10. Bailey, G.A.*; Fogg, D.E. Metathesis of Electron-Deficient Olefins: Catalyst Decomposition by Phosphines. 48th Inorganic Discussion Weekend, Kingston, ON: Nov 6–8, 2015. (Regional; Oral Presentation Award) P9. Bailey, G.A.*; Fogg, D.E. Acrylate Metathesis: Origin of the Superior Performance of Phosphine-Free Ru Catalysts. 21st International Symposium on Olefin Metathesis, Graz, Austria: July 11–16, 2015. (International) P8. Bailey, G.A.*; Fogg, D.E. Deactivation of the Hoveyda Catalyst: Impact of Ethylene. 98th Canadian Chemistry Conference & Exhibition, Ottawa, ON: June 13-17, 2015. (National) P7. Bailey, G.A.*; Fogg, D.E. Acrylate-Induced Decomposition in Olefin Metathesis. 47th Inorganic Discussion Weekend, Montreal, QC: Nov 16–18, 2014. (Regional) P6. Bailey, G.A.*; Fogg, D.E. Organometallic MALDI Mass Spectrometry: Fragmentation and Survival. 19th International Symposium on Homogeneous Catalysis, Ottawa, ON: July 6–11, 2014. (International) P5. Bailey, G.A.*; Fogg, D.E. Understanding Catalyst Decomposition in Ru-Catalyzed Cross-Metathesis of Acrylates. 96th Canadian Chemistry Conference & Exhibition, City, QC: May 26–30, 2013. (National) O4. Bailey, G.A.*; Price, E.W.; Zeglis, B.M.; Ferreira, C.L.; Boros, E.; Lacasse, M.J.; Patrick, B.O.; Lewis, J.S.; Adam, M. J.; Orvig, C. A Novel Acyclic Multifunctional Chelator for 64Cu Radiopharmaceuticals. Western Canadian Undergrad. Chemistry Conf. Edmonton, AB; May 3–5, 2012. (Regional; Oral Presentation Award) O3. Bailey, G.A.*; Price, E.W.; Orvig, C. A Novel Acyclic Multifunctional Chelator for 64Cu Radiopharmaceuticals. Chemistry Undergraduate Research Conf., Vancouver, BC; Apr 3, 2012. (Institutional) O2. Bailey, G.A.*; Côté, A.; Heuft, M.A. Towards the Synthesis of a Novel Organic Semiconductor for Photoreceptor Materials. Xerox Research Centre Canada R&D meeting, Mississauga, ON; Dec 17, 2010. P1. Yang, Z.*; Bailey, G.A.*; Gray, M.R.; Chou, K.C. Interfacial Water Content & Bitumen Liberation from Silica and Mica Surfaces. Centre for Oil Sands Innovation Stewardship Meeting, Edmonton, AB; May 4–5, 2010.

PROFESSIONAL DEVELOPMENT AND SERVICE 2012–17 With D. Fogg: built a world-leading anaerobic MALDI–TOF/TOF facility at U. Ottawa. Role: (i) field tests across North America on state-of-the-art spectrometers; (ii) interface design, with engineers from 3 companies; (iii) co-drafting & review of Request for Proposals (RFP); (iv) on-site manager 2016–17 Advisor to uOttawa CHM3350/3750 lab in Transition-Metal Chemistry (Informal basis) 2014–17 Emergency Warden, Chemistry, University of Ottawa 2016 Volunteer, 24th Canadian Symposium on Catalysis, Ottawa, ON 2015 Participant in Mitacs Step workshop: Skills of Communication, Ottawa, ON 2014 Volunteer, 19th International Symposium on Homogeneous Catalysis, Ottawa, ON 2013 Volunteer, University of Ottawa Undergraduate Outreach Day 2012 Volunteer, 15th International Conference on Biological Inorganic Chemistry, Vancouver, BC 2009 Volunteer, ELMACON Elementary School Math Competition, Vancouver, BC 2009 Volunteer, UBC Science Week, Vancouver, BC 2007–08 Elected Student Representative, College of the Rockies Education Council. Role: advising Council on issues of student interest during monthly meetings. 2008 Judge, East Kootenay Regional Science Fair, Cranbrook, BC

RESEARCH POSITIONS HELD 2012–17 Ph.D. Candidate, University of Ottawa (Prof. Deryn E. Fogg) Catalyst Decomposition in Ru-Catalyzed Olefin Metathesis 2011–12 Honour’s Student, Medicinal Inorganic Chemistry, UBC (Prof. Chris Orvig, 8 months) Acyclic Chelators for Radiopharmaceutical Applications 2011 Research Assistant, Medicinal Inorganic Chemistry, UBC (Prof. Chris Orvig, 4 months; co-op) Multifunctional Prodrugs for Alzheimer’s Disease Therapy 2010 Research Assistant, Xerox Research Centre Canada (Dr. Matthew Heuft, 4 months; co-op) Novel Organic Semiconductors for Photoreceptor Materials Gwendolyn Anne Bailey

2010 Research Assistant, Tekmira Pharmaceuticals Corp. (Dr. James Heyes, 8 months; co-op) Synthesis of Novel Lipids for siRNA Therapeutic Applications 2009 Research Assistant, Physical Chemistry, UBC (Prof. Keng C. Chou, 4 months; summer research) Dynamic Contact Angle Studies of Bitumen Oil Drop Recession from a Mineral Surface

TEACHING POSITIONS HELD (University of Ottawa) 2016 Lab Demonstrator: Molecular Spectroscopy (French / English, 130 h) 2016 Teaching Assistant: Molecular Spectroscopy (French, 45 h) 2012–15 Teaching Assistant and Lab Demonstrator: Transition Metal Chemistry (French & English, 3x130 h) 2015 In-laboratory research supervisor for Tammy Bui, UROP student (2 months) 2015 In-laboratory research supervisor for Bradley Holden, summer student (4 months) 2015 Teaching Assistant & Lab Demonstrator: Physical Chemistry (French, 130 h) 2013–14 Tutor, Chemistry Help Center (French & English, 2x130 h)

COLLABORATIONS Prof. Vidar Jensen (University of Bergen, Norway; base-induced decomposition of Ru olefin metathesis catalysts) Prof. Eduardo dos Santos (U. Federale de Minas Gerais, Brazil; polyphenol-enabled acrylate metathesis) Bruker Daltonics R&D (Billerica, MA headquarters; anaerobic MALDI–glovebox interface) Shimadzu/Kratos Analytical R&D (Manchester, UK headquarters; anaerobic MALDI–glovebox interface) MBraun R&D (Stratham, NH; anaerobic MALDI–glovebox interface) Nordion R&D (TRIUMF facility, Vancouver, BC; multifunctional chelators for radiopharmaceutical applications)

OTHER INTERESTS Traveling (with travel to 25 countries worldwide); languages (fluent in French, English, German; working knowledge of Spanish, Catalan); Romanesque art and architecture; literature; finance; LaTeX; classical music; ARCT (teaching)-level piano-playing abilities; Grade 10 Royal Conservatory piano exam (with honours); painting; drawing; meditation; fitness; running (Victoria half-marathon chip time: 1h50); badminton; outdoors.