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Douglas Group

Chemistry Publications CV

Douglas
Group

SPONSORS

ACS-PRF — American Chemical Society, Petroleum Research Fund, New Directions grant

University of Minnesota, Research Infrastructure Reinvestment Program Grant

University of Minnesota, George Taylor Career Development Award

NSF CAREER Award

NIH, National Institute of General Medical Sciences, R01 Type Award

FORMER SPONSORS

NSF, University of Minnesota Materials Research Science and Engineering Center (MRSEC)

Dupont — 2011 DuPont Young Investigator Award

Research Corporation for Science Advancement, Cottrell Scholar Award

University of Minnesota, Laboratory Startup Funds

3M Non-tenured Faculty Grant Award

University of Minnesota, Institute on the Environment, Initiative for Renewable Energy and the Environment (IREE)

ACS-PRF — American Chemical Society, Petroleum Research Fund, Starter Grant Type G

Department of Chemistry Douglas Group Publications Group Members Douglas CV Links Outreach

Text-only · From supervised career · Douglas CV

PUBLICATIONS


37. Studies towards the Total Synthesis of Drimentine C. Preparation of the AB and CDEF Ring Fragments
Authors: Pound, S. M.; Underwood, S. J.; Douglas, C. J.
References: European Journal of Organic Chemistry 2020, 2448–2453.


36. Preparation of bis-Benzyne Precursor 2,5-bis(Trimethylsilyl)-1,4-Phenylene bis(Trifluoromethanesulfonate)
Authors: Carpenter, C. A.; Wegwerth, S. E.; Douglas, C. J.
References: Organic Preparations and Procedures International, 2019, 51, 498–502.


35. Synthesis of the Madangamine Alkaloid Core by a C–C Bond Activation Cascade
Authors: Eastwood, M. S.; Douglas, C. J.
References: Organic Letters, 2019, 21, 6149–6154.


34. Rubrene Versus Fluorine-Functionalized Rubrene Molecules on a Metal Surface: Self-Assembly, Electronic Structure, and Energy Alignment of a Monolayer on Ag(100)
Authors: Viereck, J.; Rangan, S.; Häberle, P.; Galoppini, E.; Douglas, C. J.; Bartynski, R. A.
References: Journal of Physical Chemistry C, 2019, 123, 14382–14390.


33. Chemoselectivity for Alkene Cleavage by Palladium-Catalyzed Intramolecular Diazo Group Transfer from Azide to Alkene
Authors: Frost, G. B.; Mittlestaedt, M. N.; Douglas, C. J.
References: Chemistry A European Journal, 2019, 25, 1727–1732.


32. Integrating Metal-Catalyzed C–H and C–O Functionalization To Achieve Sterically Controlled Regioselectivity in Arene Acylation
Authors: Serratore, N. A.; Anderson, C. B.; Frost, G. F.; Hoang, G.–T.; Underwood, S. J.; Gemmel, P. M.; Hardy, M. A.; Doughas, C. J.
References: The Journal of the American Chemical Society, 2018, 140, 10025.


31. Morphological, Chemical, and Electronic Changes of the Conjugated Polymer PTB7 with Thermal Annealing
Authors: Savikhin, V.; Jagadamma, L. K.; Purvis, L. J.; Roterbtson, I.; Oosterhout, S. D.; Douglas, C. J.; Samuel, I. D. W.; Toney, M. F.
References: iScience 2018, 2, 182.
DOI: 10.1016/j.isci.2018.03.002


30. Palladium and Lewis-Acid-Catalyzed Intramolecular Aminocyanation of Alkenes: Scope, Mechanism, and Stereoselective Alkene Difunctionalizations
Authors: Pan, Z.; Wang, S.; Brethorst, J. T.; Douglas, C. J.
References: The Journal of the American Chemical Society 2018, 140, 3331.
DOI: 10.1021/jacs.8b01330


29. Synthesis and Characterization of Electron-Deficient Asymmetrically Substituted Diarylindenotetracenes
Authors: Purvis, L. P.; Gu, X.; Ghosh, S.; Zhang, Z.; Cramer, C. J.; Douglas, C. J.
References: The Journal of Organic Chemistry 2018, 83, 1828.
DOI: 10.1021/acs.joc.7b02756


28. Femtosecond Raman Microscopy Reveals Structural Dynamics Leading to Triplet Separation in Rubrene Singlet Fission
Authors: Bera, K.; Douglas, C. J.; Frontiera, R. R.
References: The Journal of Physical Chemistry Letters 2017, 8, 5929.
DOI: 10.1021/acs.jpclett.7b02769


27. Scanning Kelvin Probe Microscopy Reveals Planar Defects Are Sources of Electronic Disorder in Organic Semiconductor Crystals
Authors: Wu, Y.; Ren, X; McGarry, K. A.; Bruzek, M. J.; Douglas, C. J.; Frisbie, C. D.
Reference: Advanced Electronic Materials 2017, 3, 1700117.
DOI: 10.1002/aelm.201700117


26. Characterization of Five Fatty Aldehyde Dehydrogenase Enzymes From Marinobacter and Acinetobacter: Structural Insights into the Aldehyde Binding Pocket
Authors: Bertram, J. H.; Mulliner, K. M.; Shi, K.; Plunkett, M. H.; Nixon, N. A.; Serratore, N. A.; Douglas, C. J.; Aihara, H.; Barney, B. M.*
Reference: Applied and Environmental Microbiology 2017, 83, e00018-17.
DOI: 10.1128/aem.00018-17


25. Intrinsic Non-radiative Voltage Losses in Fullerene-based Organic Solar Cells
Authors: 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.*
Reference: Nature Energy 2017, 2, 17053.
DOI: 10.1038/nenergy.2017.53


24. Negative Isotope Effect on Field-Effect Hole Transport in Fully Substituted 13C-Rubrene
Authors: 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.*
Reference: Advanced Electronic Materials 2017, 3, 1700018.
DOI: 10.1002/aelm.201700018


23. Mechanistic Model for Enantioselective Intramolecular Alkene Cyanoamidation via Palladium-Catalyzed C–CN Bond Activation
Authors: Frost, G. B.†; Serratore, N. A.†; Ogilvie, J. M.; Douglas, C. J.*
Reference: The Journal of Organic Chemistry 2017, 82, 3721–3726.
DOI: 10.1021/acs.joc.7b00196


22. Development and Mechanistic Study of Quinoline-Directed Acyl C–O Bond Activation and Alkene Oxyacylation Reactions
Authors: Hoang, G. T.†; Walsh, D. J.†; McGarry, K. A.; Anderson, C. B.; Douglas, C. J.*
Reference: The Journal of Organic Chemistry 2017, 82, 2972–2983.
DOI: 10.1021/acs.joc.6b03011


21. Partial Fluorination as a Strategy for Crystal Engineering of Rubrene Derivatives
Authors: 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.*
Reference: Crystal Growth and Design 2017, 17, 643–658.
DOI: 10.1021/acs.cgd.6b01497


20. Diastereoselective Intramolecular Cyanoamidation with Alkenes
Authors: Dreis, A. M.; Otte, S. C.; Eastwood, M. S.; Alonzi, E. R.; Brethorst, J. T.; Douglas, C. J.*
Reference: European Journal of Organic Chemistry 2017, 45–48.
DOI: 10.1002/ejoc.201601283


19. Synthesis, electrochemical properties, and crystal packing of perfluororubrene
Authors: Zhang, Z.; Ogden, W. A.; Young, V. G.; Douglas, C. J.*
Reference: Chemical Communications 2016, 52, 8127–8130.
DOI: 10.1039/C6CC03259A


18. Cyclization of an alkene-bearing cyclopentanone: The role of rhodium and Brønsted acid
Authors: Jiang, X.; Pan, Z.; Douglas, C. J.*
Reference: Tetrahedron Letters 2015, 56, 5324–5327.
DOI: 10.1021/j.tetlet.2015.07.086


17. Intramolecular Oxyacylation of Alkenes Using a Hydroxyl Directing Group
Authors: Hoang, G. T.; Pan, Z.; Brethorst, J. T.; Douglas, C. J.*
Reference: The Journal of Organic Chemistry 2014, 79, 11383–11394.
DOI: 10.1021/jo501814n


16. Palladium catalyzed intramolecular acylcyanation of alkenes using α‑iminonitriles
Authors: Rondla, N. R.; Ogilvie, J. M.; Pan, Z.; Douglas, C. J.*
Reference: Chemical Communications 2014, 50, 8974–8977.
DOI: 10.1039/C4CC04068F


15. Intramolecular Aminocyanation of Alkenes by N–CN Bond Cleavage
Authors: Pan, Z.; Pound, S. M.; Rondla, N. R.; Douglas, C. J.*
Reference: Angewandte Chemie International Edition 2014, 53, 5170–5174.
DOI: 10.1002/anie.201310983

14. Carbon–Carbon Bond Activation with 8-Acylquinolines
Authors: Dreis, A. M.; Douglas, C. J.*
Reference: Topics in Current Chemistry 2014.
DOI: 10.1007/128_2013_523


13. Utilizing Carbon Nanotube Electrodes to Improve Charge Injection and Transport in Bis(trifluoromethyl)-Dimethyl-Rubrene (fm-rubrene) Ambipolar Single Crystal Transistors
Authors: 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.*
Reference: ACS Nano 2013, 7, 10245–10256.
DOI: 10.1021/nn4045694


12. Connecting Molecular Structure and Exciton Diffusion Length in Rubrene Derivatives
Authors: Mullenbach, T. K.; McGarry, K. A.; Luhman, W. A.; Douglas, C. J.*; Holmes, R. J.*
Reference: Advanced Materials 2013, 25, 3689‑3693.
DOI: 10.1002/adma.201300641


11. Rubrene-Based Single-Crystal Organic Semiconductors: Synthesis, Electronic Structure, and Charge-Transport Properties
Authors: McGarry, K. A.; Xie, W.; Sutton, C.; Risko, C.; Wu, Y.; Young, V. G.; Brédas, J.‑L.; Frisbie, C. D.*; Douglas, C. J.*
Reference: Chemistry of Materials 2013, 25, 2254‑2263.
DOI: 10.1021/cm400736s


10. High‑Mobility Transistors Based on Single Crystals of Isotopically Substituted Rubrene‑ d28
Authors: Xie, W.; McGarry, K. A.; Liu, F.; Wu, Y.; Ruden, P. P.; Douglas, C. J.*; Frisbie, C. D.*
Reference: The Journal of Physical Chemistry C 2013, 117, 2254‑2263.
DOI: 10.1021/jp402250v


9. Cooperative Catalysis Approach to Intramolecular Hydroacylation
Authors: Beletskiy, E. V.; Sudheer, C.; Douglas, C. J.*
Reference: The Journal of Organic Chemistry 2012, 77, 5884‑5893.
DOI: 10.1021/jo300779q
Notes: Feature Article


8. Diarylindenotetracences via Selective Cross‑Coupling/C–H Functionalization: Electron Donors for Organic Photovoltaic Cells
Authors: Gu, X.; Luhman, W. A.; Yagodkin, E.; Holmes, R. J.*; Douglas, C. J.*
Reference: Organic Letters 2012, 14, 1390‑1393.
DOI: 10.1021/ol300098p


7. Preparation of 6,11-Dihydroxy-5,12-Tetracenedione
Authors: Yagodkin, E.; McGarry, K. A.; Douglas, C. J.*
Reference: Organic Preparations and Procedures International 2011, 43, 360‑363.
DOI: 10.1080/00304948.2011.594006


6. Palladium-Catalyzed CC–CN Activation for Intramolecular Cyanoesterification of Alkynes
Authors: Rondla, N. R.; Levi, S. M.; Ryss, J. M.; Vanden Berg, R. A.; Douglas, C. J.*
Reference: Organic Letters 2011, 13, 1940‑1943.
DOI: 10.1021/ol200274h


5. Intramolecular Oxyacylation Reaction of Alkenes via Acyl C–O Bond Activation
Authors: Hoang, G. T.; Reddy, V. J.; Nguyen, H. H. K.; Douglas, C. J.*
Reference: Angewandte Chemie International Edition 2011, 50, 1882‑1884.
DOI: 10.1002/anie.201005767
Notes: Selected by the Editorial Board as a 'Hot Paper' and highlighted by Nachrichten aus der Chemie


4. Low Temperature Kumada‑Corriu Cross‑Coupling of Polychlorinated Acene Derivatives and a Synthesis of Sterically Demanding Acenes
Authors: Yagodkin, E.; Douglas, C. J.*
Reference: Tetrahedron Letters 2010, 51, 3037‑3040
DOI: 10.1016/j.tetlet.2010.03.121


3. Synthesis, Solid State Properties, and Semiconductor Measurements of 5,6,11,12-Tetrachlorotetracene
Authors: Yagodkin, E.; Xia, Y.; Kalihari, V.; Frisbie, C. D.*; Douglas, C. J.*
Reference: Journal of Physical Chemistry C. 2009, 113, 16544‑16548.
DOI: 10.1021/jp904476z


2. Chemoselectivity in Catalytic C–C and C–H Bond Activation: Controlling Intermolecular Carboacylation and Hydroarylation of Alkenes
Authors: Wentzel, M. T.; Reddy, V. J.; Hyster, T. K.; Douglas, C. J.*
Reference: Angewandte Chemie International Edition 2009, 48, 6121‑6123.
DOI: 10.1002/anie.200902215


1. Catalytic Carbon–Carbon σ Bond Activation: An Intramolecular Carbo-Acylation Reaction
Authors: Dreis, A. M.; Douglas, C. J.*
Reference: Journal of the American Chemical Society 2009, 131, 412‑413.
DOI: 10.1021/ja8066308

Text-only · From supervised career · Douglas CV

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