University of Minnesota
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Douglas Group

Group Members
Chemistry Publications CV

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PhD Graduates

Jason Brethorst
Jason Brethorst
Education & Experience
2017 Ph.D. Chemistry, University of Minnesota, Twin Cities
Thesis: Development of Carbon‒Carbon, Carbon‒Nitrogen, and Carbon‒Hydrogen Bond Functionalization Methodologies and Efforts Toward the Total Synthesis of Dragmacidin E
2017 Organic Chemistry Lecturer, Augsburg College, CHM 352
2011 B.S. Chemistry, Saint Cloud State University
Advisor: Mark Mechelke
Douglas Group Publications
"Diastereoselective Intramolecular Cyanoamidation with Alkenes" Dreis, A. M.; Otte, S. C.; Eastwood, M. S.; Alonzi, E. R.; Brethorst, J. T.; Douglas, C. J.* Eur. J. Org. Chem. 2017, 45–48.
"Intramolecular Oxyacylation of Alkenes Using a Hydroxyl Directing Group" Hoang, G. T.; Pan, Z.; Brethorst, J. T.; Douglas, C. J.* J. Org. Chem. 2014, 79, 11383–11394.
Research keywords
Total synthesis
Bond Activation
Moved to
Instructor at St. Cloud State University
Sarah "Wegs" Wegwerth
Education & Experience
2017 Ph.D. Chemistry, University of Minnesota, Twin Cities
Thesis: Studies into the Synthesis of Cyclacenes
2017 Organic Lecturer, UMN, CHEM 2302
2013–2016 Head organic teaching assistant
2011 B.S. Chemistry, Saint Cloud State University
Advisor: Mark Mechelke
Douglas Group Publications
"Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives" Ogden, W. A.; Ghosh, S.; Bruzek, M. J.; McGarry, K. A.; Balhorn, L.; Young, V. G.; Purvis, L. J.; Wegwerth, S. E.; Zhang, Z.; Serratore, N. A.; Cramer, C. J.*; Gagliardi, L.*; Douglas, C. J.* Cryst. Growth Des. 2017, 17, 643–658.
Honors
2016 CSE Bowers Excellence in Teaching Assistance Award
2014 Bunsen and Beaker Award, Best Presentation in Section, Third-Year Research Symposium
2012–2013 Wayland E. Noland Outstanding Teaching Assistant Award
Research keywords
Acenes
Cyclacenes
Crystal Engineering
Sarah Pound
Education & Experience
2016 Ph.D. Chemistry, University of Minnesota, Twin Cities
Thesis: Development of an Intramolecular Alkene Aminocyanation Reaction and Progress Toward the Total Synthesis of Drimentine C
2011 B.S. Chemistry and Biochemistry (double major), Bethel University
Advisor: Trey Maddox
Douglas Group Publications
"Intramolecular Aminocyanation of Alkenes by N–CN Bond Cleavage" Pan, Z.; Pound, S. M.; Rondla, N. R.; Douglas, C. J.* Angewandte Chemie International Edition 2014, 53, 5170–5174.
Research keywords
Bond activation
Methodology
Total synthesis
Moved to
Postdoctoral Associate with Professor Mary Watson, University of Delaware
Naveen Rondla
Naveen Rondla
Education & Experience
2013 Ph.D. Chemistry, University of Minnesota, Twin Cities
Thesis: Development of New Reaction Methodologies Using Palladium Catalysts
2011‑2012 Internship, GlaxoSmithKline, Research Triangle Park NC
2008 M.Sc. Chemistry, Indian Institute of Technology, Kanpur, India.
Advisor: Sandeep Verma
2006 B.Sc. Chemistry, Osmania University, India
Honors
2008‑2009 Dr. Venkateswarlu Pothapragada and Family Graduate Fellowship
Douglas Group Publications
"Palladium catalyzed intramolecular acylcyanation of alkenes using α‑iminonitriles" Rondla, N. R.; Ogilvie, J. M.; Pan, Z.; Douglas, C. J.* Chemical Communications 2014, 50, 8974–8977.
"Intramolecular Aminocyanation of Alkenes by N–CN Bond Cleavage" Pan, Z.; Pound, S. M.; Rondla, N. R.; Douglas, C. J.* Angewandte Chemie International Edition 2014, 53, 5170–5174.
"Palladium-Catalyzed CC–CN Activation for Intramolecular Cyanoesterification of Alkynes" Rondla, N. R.; Levi, S. M.; Ryss, J. M.; Vanden Berg, R. A.; Douglas, C. J.* Organic Letters 2011, 13, 1940–1943.
Research keywords
Bond activation
Methodology
Moved to
Forest Laboratories, New York
Katie McGarry
Katie McGarry
Education & Experience
2013 Ph.D. Chemistry, University of Minnesota, Twin Cities
Thesis: Synthesis and Crystal Design of Rubrene Derivatives for Use in Organic Electronics
2008 B.S. Chemistry, University of Saint Thomas
Advisor: J. Thomas Ippoliti
Douglas Group Publications
"Energy-Gap Law for Non-Radiative Recombination in Fullerene Based Organic Solar Cells" Benduhn, J.*; Tvingstedt, K.; Piersimoni, F.; Ullbrich, S.; Fan, Y.; Tropiano, M.; McGarry, K. A.; Douglas, C. J.; Zeika, O.; Riede, M.; Marder, S.; Neher, D.; Spoltore, D.; Vanderwal, K.* Nat. Energy 2017, 2, 17053.
"Development and Mechanistic Study of Quinoline-Directed Acyl C–O Bond Activation and Alkene Oxyacylation Reactions" Hoang, G. T.; Walsh, D. J.; McGarry, K. A.; Anderson, C. B.; Douglas, C. J.* J. Org. Chem. 2017, 82, 2972–2983.
"Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives" Ogden, W. A.; Ghosh, S.; Bruzek, M. J.; McGarry, K. A.; Balhorn, L.; Young, V. G.; Purvis, L. J.; Wegwerth, S. E.; Zhang, Z.; Serratore, N. A.; Cramer, C. J.*; Gagliardi, L.*; Douglas, C. J.* Cryst. Growth Des. 2017, 17, 643–658.
"Utilizing Carbon Nanotube Electrodes to Improve Charge Injection and Transport in Bis(trifluoromethyl)-Dimethyl-Rubrene (fm-rubrene) Ambipolar Single Crystal Transistors" Xie, W.; Prabhumirashi, P. L.; Nakayama, Y.; McGarry, K. A.; Geier, M. L.; Uragami, Y.; Mase, K.; Douglas, C. J.; Ishii, H.; Hersam, M. C.; Frisbie, C. D.* ACS Nano 2013, 7, 10245–10256.
"Connecting Molecular Structure and Exciton Diffusion Length in Rubrene Derivatives" Mullenbach, T. K.; McGarry, K. A.; Luhman, W. A.; Douglas, C. J.*; Holmes, R. J.* Advanced Materials 2013, 25, 3689–3693.
"Rubrene-Based Single-Crystal Organic Semiconductors: Synthesis, Electronic Structure, and Charge-Transport Properties" McGarry, K. A.; Xie, W.; Sutton, C.; Risko, C.; Wu, Y.; Young, V. G.; Brédas, J.‑L.; Frisbie, C. D.*; Douglas, C. J.* Chemistry of Materials 2013, 25, 2254–2263.
"Mobility Transistors Based on Single Crystals of Isotopically Substituted Rubrene‑ d28" Xie, W.; McGarry, K. A.; Liu, F.; Wu, Y.; Ruden, P. P.; Douglas, C. J.*; Frisbie, C. D.* The Journal of Physical Chemistry C 2013, 2254–2263.
"Preparation of 6,11-Dihydroxy-5,12-Tetracenedione" Yagodkin, E.; McGarry, K. A.; Douglas, C. J.* Organic Preparations and Procedures International 2011, 43, 360–363.
Moved to
Assistant Professor at University of Wisconsin, Stevens Point
Giang Hoang
Giang Hoang
Education & Experience
2012 Ph.D. Chemistry, University of Minnesota, Twin Cities
Thesis: Development of New Reaction Methodologies via Transition Metal Catalyzed Bond Activation Processes
2004 B.S. Chemistry, National University of Singapore
Teck-Peng Loh
Honors
2010 Third-Year Graduate Student Seminar Awardee
2007‑2008 Graham N. Gleysteen Fellowship in Chemistry (4.0 GPA for Class Beginning Fall 2007)
Douglas Group Publications
"Development and Mechanistic Study of Quinoline-Directed Acyl C–O Bond Activation and Alkene Oxyacylation Reactions" Hoang, G. T.; Walsh, D. J.; McGarry, K. A.; Anderson, C. B.; Douglas, C. J.* J. Org. Chem. 2017, 82, 2972–2983.
"Intramolecular Oxyacylation of Alkenes Using a Hydroxyl Directing Group" Hoang, G. T.; Pan, Z.; Brethorst, J. T.; Douglas, C. J.* J. Org. Chem. 2014, 79, 11383–11394.
"Intramolecular Oxyacylation Reaction of Alkenes via Acyl C–O Bond Activation" Hoang, G. T.; Reddy, V. J.; Nguyen, H. H. K.; Douglas, C. J.* Angewandte Chemie International Edition 2011, 50, 1882–1884.
Moved to
Instructor at National University of Singapore
Michael Wentzel
Michael Wentzel
Education & Experience
2011 Ph.D. Chemistry, University of Minnesota, Twin Cities
Thesis: Development of Carbon-Carbon Sigma Bond Activation with Rhodium Catalysts
2009‑2011 Head organic teaching assistant
2007 M.S. Chemistry, University of Pennsylvania
Advisor: Marisa C. Kozlowski
2005 B.S. Chemistry and Philosophy, Creighton University
Douglas Group Publications
"Chemoselectivity in Catalytic C–C and C–H Bond Activation: Controlling Intermolecular Carboacylation and Hydroarylation of Alkenes" Wentzel, M. T.; Reddy, V. J.; Hyster, T. K.; Douglas, C. J.* Angewandte Chemie International Edition 2009, 48, 6121–6123.
Moved to
Instructor at Augsburg College
Postdoctoral Fellow with Professor Tom Hoye

2017

2016

Philipp Gemmel
Philipp Gemmel
Education & Experience
Fall 2017–present Ph. D. Chemistry, University of Chicago

2017 B.A. Chemistry & Political Science, Grinnell College (projected)
Advisor: Martin Minelli
2016 Lando REU fellowship, Douglas Group
Mentor
Conne Anderson
Steve Underwood
Michaela Mittlestaedt
Michaela Mittlestaedt
Mentor
Grant Frost
Joined
Summer 2015
Mingzhe Huang
Mingzhe Huang
Mentor
Zhuoran Zhang
Joined
Summer 2014
Russell Xu
Russell Xu
Mentor
Sarah Pound
Joined
Spring 2015

2015

Melissa Hardy
Melissa Hardy
Education & Experience
Fall 2016–Present Ph.D. Chemistry, UC Berkeley
Advisor: Richmond Sarpong
2016 B.A. Chemistry & French, Grinnell College
Advisor: Stephen Sieck
2015 Lando REU fellowship, Douglas Group
Mentor
Nick Serratore
David Detloff
David Detloff
Mentor
Sarah Wegwerth
Joined
Spring 2015
Nate Lawdenski
Nate Lawdenski
Mentor
Nick Serratore
Joined
Summer 2014
Preston Bradley
Preston Bradley
Mentor
Sadie Otte
Joined
Spring 2015

2014

Matt Bruzek, Ph.D.
Education & Experience
2013-2014 Postdoctoral Researcher, Douglas Group
2013 Ph.D. Chemistry, University of Kentucky
Advisor: John Anthony

Thesis: Acenes and acenequinones for optics and organic electronics
2008 B.S. Chemistry, Southwest Minnesota State University
Advisor: Jay Brown
Douglas Group Publications
"Negative Isotope Effect on Field-Effect Hole Transport in Fully Substituted 13C-Rubrene" Ren, X.*; Bruzek, M. J.; Hanifi, D. A.; Schulzetenberg, A.; Wu, Y.; Kim, C. H.; Zhang, Z.; Johns, J. E.; Salleo, A.; Fratini, S.; Troisi, A.; Douglas, C. J.; Frisbie, C. D.* Adv. Electron. Mat. 2017, 3, 1700017.
Moved to
Senior Research Chemist at 3M
Daniel Everson, Ph.D.
Education & Experience
2013-2014 Postdoctoral Researcher, Douglas Group
2013 Ph.D. Chemistry, University of Rochester
Advisor: Daniel J. Weix

Thesis: Nickel-catalyzed electrophile cross-coupling of aryl halides with alkyl halide
2007 B.S. Chemistry, University of Saint Thomas
Advisor: J. Thomas Ippoliti
Research keywords
Total synthesis
Methodology
Bond activation
Moved to
Assistant Professor at California State University, Chico
Yong Guan
Yong Guan, Ph.D.
Education & Experience
2012-2014 Postdoctoral Researcher, Douglas Group
2012 Ph.D. Chemistry, Michigan State University
Advisor: William Wulff
2006 M.S. Chemistry, Wuhan University, China
Advisors: Jun Li & Jingui Qin
2004 B.S. Chemistry, Wuhan University, China
Research keywords
Organic electronic materials
Methodology
Moved to
Postdoctoral Researcher, Steve Townsend, Vanderbilt University
Billy Ogden
William "Billy" Ogden
Education & Experience
Fall 2014–Present Ph.D. Chemistry, University of California-Irvine
Advisor: Zhibin Guan
2014 B.S. Chemistry, University of Minnesota 
2012-2014 Researcher, Douglas Group
Douglas Group Publications
"Synthesis, electrochemical properties, and crystal packing of perfluororubrene" Zhang, Z.; Ogden, W. A.; Young, V. J.; Douglas, C. J.* Chem. Commun. 2016, 52, 8127–8130.
Honors
2013 Heisig/Gleysteen Summer Research Fellowship
2012 UROP Researcher
Research keywords
Crystal engineering
Organic electronic materials
Organic electronic devices
Rubrene
Dylan Walsh
Dylan Walsh
Education & Experience
Fall 2014–Present Ph.D. Chemical Engineering, University of Illinois Urbana-Champaign
Advisor: Damien Guironnet
2014 B.E. Chemical Engineering and B.S. Chemistry, University of Minnesota 
2011-2014 Researcher, Douglas Group
Douglas Group Publications
"Development and Mechanistic Study of Quinoline-Directed Acyl C–O Bond Activation and Alkene Oxyacylation Reactions" Hoang, G. T.; Walsh, D. J.; McGarry, K. A.; Anderson, C. B.; Douglas, C. J.* J. Org. Chem. 2017, 82, 2972–2983.
Honors
2013 Heisig/Gleysteen Summer Research Fellowship
2012 Heisig/Gleysteen Summer Research Fellowship (two consecutive summers)
2012 Andrews Award
Moved to
Department of Chemical Engineering, University of Illinois at Urbana-Champaign
Xin Jiang
Xin Jiang
Education & Experience
2014 M.S. Chemistry, University of Minnesota 
2012 B.A. Natural Sciences (Physical), Cambridge University, UK
Douglas Group Publications
"Cyclization of an alkene-bearing cyclopentanone: The role of rhodium and Brønsted acid" Jiang, X.; Pan, Z.; Douglas, C. J.* Tetrahedron Lett. 2015, 56, 5324–5327.
Jodi Ogilvie, Ph.D.
Education & Experience
2012-2014 Postdoctoral Associate, Douglas Group
2012 Ph.D. Chemistry, University of Vermont
Advisor: Matthias Brewer

Thesis: Exploration of the reactivity of 1-aza-2- azoniaallene salts as precursors to alpha-chloroazo compounds, bicyclic diazenium salts and protonated azomethine imines
2006 B.S. Chemistry, University of Maine
Advisor: Barbara Cole
Douglas Group Publications
"Mechanistic Model for Enantioselective Intramolecular Alkene Cyanoamidation via Palladium-Catalyzed C–CN Bond Activation" Frost, G. B.; Serratore, N. A.; Ogilvie, J. M.; Douglas, C. J.* 2017, 82, 3721–3726.
"Palladium catalyzed intramolecular acylcyanation of alkenes using α‑iminonitriles" Rondla, N. R.; Ogilvie, J. M.; Pan, Z.; Douglas, C. J.* Chemical Communications 2014, 50, 8974–8977.
Research keywords
Bond activation
Mechanistic studies
Methodology
Kinetic studies
Moved to
Chemical Hygiene Officer, Department of Environmental Health and Safety, University of Minnesota

2013

Vicki Chemistruck
Vicki Chemistruck
Education & Experience
2012 M.S. Chemistry, University of Minnesota
2010‑2013 Graduate Researcher, Douglas and Frisbie Groups
2010 B.S. Chemistry, San Jose State University
Advisor: David J. R. Brook
Honors
2011 NSF Graduate Research Fellow
2010‑2011 Outstanding Teaching Assistant
Hanna Macaranas
Hanna Macaranas
Joined
Summer 2013
Education & Experience
2012 B.S. Chemistry, University of Southern California
Advisor: Barry C. Thompson
Research keywords
Organoelectronic materials
Acenes
Polyacenes
Diana Cedillo
Diana Cedillo
Education & Experience
2015 B.S. Chemistry, University of Texas, Pan American
Advisor: Jose Gutierrez
2013 NSF REU fellowship, Douglas Group
Research keywords
Crystal engineering
Organoelectronic materials
Rubrene
Claire Simpson
Claire Simpson
Education & Experience
2014 H.S., Breck School (projected)
2013 High school researcher, Douglas Group.
Mentor: Sarah Pound
Research keywords
Total synthesis
Ziyu Zhang
Ziyu Zhang
Education & Experience
2011‑2013 Graduate researcher, Douglas Group
2011 B.S. Chemistry, Wuhan University, China.
Advisor: Zixing Shan
Joy Zhou
Joy Zhou
Education & Experience
2013 B.S. Chemistry, University of Minnesota, Twin Cities
2011‑2013 Undergraduate researcher, Douglas Group
Mentor: Wayne Gu
2011 REU, University of North Texas
Advisor: W. Justin Youngblood
Honors
2012 Heisig/Gleysteen Summer Research Fellow
Moved to
Cargill Industrial Oils and Lubricants

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