Kent Sugden
Email
Faculty
Orion Berryman
Associate Professor & Director of Small Molecule X-ray Diffraction Facility
Office: Chem 207Email: orion.berryman@umontana.edu
Fax: (406) 243-4227
Personal Website
Curriculum Vitae
Current Position
Associate professor, Department of Chemistry & Biochemistry
Director of Small Molecule X-ray Diffraction Facility, Center for Biomolecular Structure & Dynamics
Courses
CHMY 223 Organic Chemistry II
CHMY 222 Organic Chemistry I Lab
CHMY 292 Independant Study
CHMY 490 Undergraduate Research
CHMY 492 Independent Study
CHMY 499 Senior Thesis
CHMY 562 Organic Structure and Mechanism
CHMY 580 Supramolecular Research Survey
CHMY 595 Physical Organic Chemistry
CHMY 597 Research
CHMY 630 Departmental Seminar
CHMY 690 Research
Personal Summary
Orion grew up enjoying the great outdoors surrounding Homer, Alaska. In 2003 Orion received a B.A. in chemistry and a minor in music from the University of New Hampshire. For postbaccalaureate studies Orion attended the University of Oregon--earning a Ph D. in organic/inorganic chemistry in 2008. During his doctoral studies Orion helped define the nature of anion/arene interactions under the guidance of Darren W. Johnson. Postdoctoral studies led Orion to The Scripps Research Institute in La Jolla, CA where he worked for Julius Rebek Jr. developing light responsive catalysts and ligands that encapsulate uranium. In 2012 Orion joined the chemistry and biochemistry faculty at the University of Montana. Orion is a CoBRE investigator within the Center for Biomolecular Structure and Dynamics where he will teach and develop new catalysts that utilize noncovalent interactions as well as self-assembled ligands for ion remediation.
Education
University of New Hampshire 1999-2003 -- B.A. Chemistry, Minor music
University of Oregon 2003-2008 -- Ph.D. Organic and Inorganic Chemistry
The Scripps Research Institute 2008-2012
Research Interests
APPLIED MOLECULAR RECOGNITION
My laboratory works at the interfaces of organic/inorganic chemistry, supramolecular chemistry and chemical biology. This interdisciplinary environment affords many opportunities to collaborate and apply concepts of molecular recognition. We develop novel uses for noncovalent interactions and apply them to outstanding and socially relevant problems in chemistry. To reach our targets we employ preparative and analytical techniques including; organic/organometallic synthesis, crystallography, computations, UV-Vis, fluorescence and NMR. When successful we will transform how molecular design is approached with focus on noncovalent interactions.
For further details please follow the link to my lab website:
Field of Study
organic chemistry, catalysis, molecular recognition, self-assembly, ligand development, photoisomerization
Publications
PEER-REVIEWED PUBLICATIONS
39. Massena, C. J.; Decato, D. A.; Berryman, O. B.* "A Longâ€Lived Halogenâ€Bonding Anion Triple Helicate Accommodates Rapid Guest Exchange." Angewandte Chemie International Edition, 2018, 57, 16109–16113.
38. Wageling, N. B.; Decato, D. A.; Berryman, O. B.* "Steric Effects of pH Switchable, Substituted (2-pyridinium)urea Organocatalysts: a Solution and Solid Phase Study." Supramolecular Chemistry, 2018, 30, 1004–1010.
37. Riel A. M. S.‡; Decato, D. A.‡; Sun J.; Massena, C. J.; Jessop, M. J.; Berryman, O. B.* “The Intramolecular Hydrogen Bonded–Halogen Bond: A New Strategy for Preorganization and Enhanced Binding.” Chemical Science, 2018, 9, 5828–5836.
- ‡Both authors contributed equally.
36. Sun, J.; Riel A. M. S.; Berryman, O. B.* “Solvatochromism and Fluoresence Response of a Halogen Bonding Anion Receptor.” New Journal of Chemistry, 2018, 42, 10489–10492.
35. Riel, A. M. S.; Jessop, M. J.†; Decato, D. A.; Massena, C. J.; Nascimento, V. R.†; Berryman, O. B.* ”Experimental Evidence of Halogen Bond Hard-Soft Acid Base Complementarity.” Acta Crystallographica Section B, 2017, B73, 203-209.
34. Massena, C. J.; Wageling, N. B.; Decato, D. A.; Rodriguez, E. M.†; Berryman, O. B.* “A Halogen Bond Induced Triple Helicate Encapsulates Iodide.” Angewandte Chemie International Edition 2016, 55, 12398-12402.
- Cover art and UM press release
33. Riel, A. M. S.; Decato, D. A.; Berryman, O. B.* “Protonation and Alkylation Induced Multidentate C–H•••Anion Binding to Perrhenate.” Crystal Growth and Design, 2016, 16, 974-980.
32. Wageling, N. B.‡; Neuhaus, G. F.‡†; Rose, A. M.; Decato, D. A.; Berryman, O. B.* “Advantages of Organic Halogen Bonding for Halide Recognition.” Supramolecular Chemistry, 2016, 28, 665-672.
31. Massena, C. J.; Riel, A. M. S.; Neuhaus, G. F.; Decato, D. A.; Berryman, O. B.* “Solution and Solid-Phase Halogen and C-H Hydrogen Bonding to Perrhenate.” Chemical Communications, 2015, 51, 1417-1420.
30. Decato, D. A.; Berryman, O. B.* “Crystal Structure of [1,1':3',1''-Terphenyl]-2',3,3''-Tricarboxylic Acid.” Acta Crystallographica Section E, 2015, 71, o667-o668.
29. Tresca, B. W.; Berryman, O. B.; Zakharov, L. N.; Johnson, D. W.; Haley, M. M.* “Anion-Directed Self-Assembly of a 2,6-bis(2-Anilinoethynyl)pyridine Bis(amide) scaffold.” Supramolecular Chemistry, 2015, DOI: 10.1080/10610278.2015.1072199.
28. Berryman, O. B.; Johnson, C. A.; Vonnegut, C. L.; Fajardo, K. A.; Zakharov, L. N.; Johnson, D. W.; Haley, M. M. “Solid-State Examination of Conformationally Diverse Sulfonamide Receptors Based on Bis(2-anilinoethynyl)pyridine, -Bipyridine, and -Thiophene.” Crystal Growth and Design, 2015, 15, 1502-1511.
27. Sather, A. C.; Berryman, O. B.; Rebek, J. Jr. “Selective Recognition and Extraction of the Uranyl Ion from Aqueous Solutions with a Recyclable Chelating Resin.” Chemical Science, 2013, 4, 3601-3605.
26. Sather, A. C.; Berryman, O. B.; Moore, C. E.; Rebek, J. Jr. “Uranyl Ion Coordination with Rigid Aromatic Carboxylates and Structural Characterization of their Complexes.” Chemical Communications, 2013, 49, 6379-6381.
25. Collins, M. S.; Carnes, M. E.; Sather, A. C.; Berryman, O. B.; Zakharov, L. N.; Teat, S. J.; Johnson, D. W. “Pnictogen-Directed Synthesis of Discrete Disulfide Macrocycles.” Chemical Communications, 2013, 49, 6599-6601.
24. Sather, A. C.; Berryman, O. B.; Rebek, J. Jr. “Synthesis of Fused Indazole Ring Systems and Application to Nigeglanine hydrobromide.” Organic Letters, 2012, 14, 1600-1603.
23. Berryman, O. B.; Sather, A. C.; Lledo, A.; Rebek, J. Jr. “Switchable Catalysis with a Light Responsive Cavitand.” Angewandte Chemie International Edition, 2011, 50, 9400-9403.
- Editor designated “hot paper” for importance in field of high interest.
22. Berryman, O. B.; Sather, A. C.; Rebek, J. Jr. “A Deep Cavitand with a Fluorescent Wall Functions as an Ion Sensor.” Organic Letters, 2011, 13, 5232-5235.
21. Berryman, O. B.; Dube, H.; Rebek, J. Jr. “Photophysics Applied to Cavitands and Capsules.” Israel Journal of Chemistry, 2011, 51, 700-709.
- Invited review article
20. Fontenot, S. A.; Cangelosi, V. M.; Pitt, M. A. W.; Sather, A. C.; Zakharov, L. N.; Berryman, O. B.; Johnson, D. W. “Design, Synthesis and Characterization of Self-Assembled As2L3 and Sb2L3 Cryptands.” Dalton Transactions, 2011, 40, 12125-12131.
19. Gavette, J. V.; Lara, J.; Berryman, O. B.; Zakharov, L. N.; Haley, M. M.; Johnson, D. W. “Lithium Cation Enhances Anion Binding in a Tripodal Phosphine Oxide-Based Ditopic Receptor.” Chemical Communications, 2011, 47, 7653-7655.
18. Carroll, C. N.; Coombs, B. A.; McClintock, S. P.; Johnson, C. A.; Berryman, O. B.; Johnson, D. W.; Haley, M. M. “Anion-Dependent Fluorescence in Bis(anilinoethynyl)pyridine Derivatives: Switchable ON-OFF and OFF-ON responses.” Chemical Communications, 2011, 47, 5539-5541.
17. Berryman, O. B.; Sather, A. C.; Rebek, J. Jr. “A Light Controlled Cavitand Wall Regulates Guest Binding.” Chemical Communications, 2011, 47, 656-658.
16. Sather, A. C.; Berryman, O. B.; Ajami, D.; Rebek, J. Jr. “Reactivity of N-nitrosoamides in Confined Spaces.” Tetrahedron Letters, 2011, 52, 2100-2103.
15. Sather, A. C.; Berryman, O. B.; Rebek, J. Jr. “Recognition and Extraction of the Uranyl Ion with a Preorganized Tripodal Ligand.” Journal of the American Chemical Society, 2010, 132, 13572-13574.
14. Beer, S.‡; Berryman, O. B.‡; Ajami, D.; Rebek, J. Jr. “Encapsulation of the Uranyl Dication.” Chemical Science, 2010, 1, 43-47.
-‡ Both authors contributed equally. Highlighted in RSC press release, UK’s Daily Telegraph, MSN news, Yahoo News and AOL news. Cover art.
13. Restorp, P.; Berryman, O. B.; Sather, A. C.; Ajami, D.; Rebek, J. Jr. “A Synthetic Receptor for Hydrogen Bonding to Fluorines of Trifluoroborates.” Chemical Communications, 2009, 5692-5694.
12. Johnson, C. A.; Berryman, O. B.; Sather A. C.; Zakharov, L. N.; Haley, M. M.; Johnson, D. W. “Anion Binding Induces Helicity in a Hydrogen Bonding Receptor: Crystal Structure of a 2,6-Bis(anilinoethynyl)pyridinium Chloride.” Crystal Growth and Design, 2009, 9, 4247-4249.
11. Berryman, O. B.; Johnson, D. W. “Experimental Evidence of Interactions Between Anions and Electron-Deficient Aromatic Rings.” Chemical Communications, 2009, 3143-3153.
- Invited feature article and cover art.
10. Carroll, C. N.; Berryman, O. B.; Johnson, C. A.; Zakharov, L. N.; Haley, M. M.; Johnson, D. W. “Protonation Activates Anion Binding and Alters Binding Selectivity in New Inherently Fluorescent 2,6-bis(2-anilinoethynyl)pyridine Bisureas.” Chemical Communications, 2009, 2520-2522.
9. Berryman, O. B.; Sather, A. C.; Meisner, J. S.; Hay, B. P.; Johnson, D. W. “Solution Phase Measurement of Both Weak Sigma Complexes and C-H•••X– Hydrogen Bonding Interactions in a Synthetic Receptor.” Journal of the American Chemical Society, 2008, 130, 10895-10897.
8. Berryman, O. B.; Johnson, C. A.; Zakharov, L. N.; Haley, M. M.; Johnson, D. W. “Water and Hydrogen Halides Serve the Same Structural Role in a Series of 2+2 Hydrogen-Bonded Dimers Based on 2,6-bis(2-anilinoethynyl)pyridine Sulfonamide Receptors.” Angewandte Chemie International Edition, 2008, 47, 117-120.
7. Shultz, G. V.; Berryman, O. B.; Zakharov, L. N.; Tyler, D. R. “Preparation of Photodegradable Polymers Containing Metal-Metal Bonds Using ADMET.” Journal of Inorganic and Organometallic Polymers and Materials, 2008, 18, 149-154.
6. Berryman, O. B.; Bryantsev, V. S.; Stay, D. P.; Johnson, D. W.; Hay, B. P. “Structural Criteria for the Design of Anion Receptors: the Interaction of Halides with Electron-Deficient Arenes.” Journal of the American Chemical Society, 2007, 129, 48-58.
- UO Press release – December 2006, sited 192 times, Web of Science designated highly cited paper.
5. Meisner, J. S.; Berryman, O. B.; Zakharov, L. N.; Johnson, D. W. “Methyl 4-bromo-3,5-dinitrobenzoate.” Acta Crystallographica Section E, 2007, 63, o2466.
4. Cangelosi, V. A.; Sather, A. C.; Zakharov, L. N.; Berryman, O. B.; Johnson, D. W. “Diastereoselectivity in the Self-Assembly of As2L2Cl2 Macrocycles is Directed by the As-π Interaction.” Inorganic Chemistry, 2007, 46, 9278-9284.
3. Berryman, O. B.; Hof, F.; Hynes, M. J.; Johnson, D. W. "Anion-π Interaction Augments Halide Binding in Solution." Chemical Communications, 2006, 506-508.
2. Johnson, C. A.; Baker, B. A.; Berryman, O. B.; Zakharov, L.; O'Connor, M. J.; Haley, M. M. "Synthesis and Characterization of Pyridine- and Thiophene-Based Platinacyclyne Topologies." Journal of Organometallic Chemistry, 2006, 691, 413-421.
1. Vickaryous, W. J.; Healey, E. R.; Berryman, O. B.; Johnson, D. W. "Synthesis and Characterization of Two Isomeric, Self-Assembled Arsenic-Thiolate Macrocycles." Inorganic Chemistry, 2005. 44, 9247-9252.
BOOK CHAPTERS
A. Berryman, O. B.*; Riel, A. M. S.; Wageling, D. A.; Decato, D. A.; Massena, C. J. “In Comprehensive Supramolecular Chemistry II: Anion-Arene Interactions and the Anion-π Phenomenon.” Atwood, J., Gokel, G., Barbour, L., Eds.; Elsevier Publishers. In press.
B. Decato, D. A.; Berryman, O. B.*; “Aspects of Multi-component Crystals: Synthesis, Concepts and Function.” Tiekink, E. R. T., Eds; De Gruyter Publishers. In press.
C. Rather Healey, E.; Vickaryous, W. J.; Berryman, O. B.; Johnson, D. W. “In BOTTOM-UP NANOFABRICATION: Supramolecules, Self-Assemblies, and Organized Films.” Ariga, K., Nalwa, H. S., Eds.; American Scientific Publishers: Stevenson Ranch, 2007.
PATENTS
I. Berryman, O. B.; Massena, C. J. “A Halogen-Bond-Induced Triple Helicate Encapsulates Iodide.” Serial No. 62/362,226, filed July 14, 2016.
I. Haley, M. M.; Johnson, D. W.; Berryman, O. B.; Johnson, C. A.; Stimpson, C. A. “Process for Preparation of Tunable Phenylacetylene Host Compounds for Ligand Binding.” U.S. Pat. Appl. US 2008167472, 2008, 21.
II. Rebek, J. Jr.; Berryman, O. B.; Sather, A. C. “Methods and Compositions for Chelating Metals in Aqueous Solutions.” US Pat. Application # 61/217,078, 2009.
Honors
2016 NSF CAREER – Halogen Bonding Catalysts
- Berryman, Lead P.I.
2015 MREDI Research Initiative – Instrumentation for Water Quality Monitoring
- Berryman, Co-P.I.
2013 NSF Major Research Instrumentation program – Single Crystal X-ray Diffractometer
- Berryman, lead P.I.
2012 NIH subproject of grant 8P20GM103546-02 (CoBRE)
Specialized Research Interests
Organic chemistry, catalysis, molecular recognition, self-assembly, ligand development, photoisomerization.
Teaching Experience
CHMY 223 Organic Chemistry II
CHMY 222 Organic Chemistry Lab I
CHMY 562 Organic Structure and Mechanism
CHMY 580 Supramolecular Research Survey
CHMY 595 Physical Organic Chemistry
CHMY 630 Departmental Seminar
Professional Experience
Organized organic symposium at ACS NORM meeting 2014
International Experience
Invited chair of microsymposium at the 24th IUCr - Hyderabad, India 2017
Rising Star Honorarium at the ISXB conference - Gothenburg, Sweden 2016
Affiliations
Center for Biomolecular Structure and Dynamics
Montana University System Materials Science Program
Hobbies
Racing around the mountains and roads on carbon fiber bikes and nordic skis.
Filling the neighborhood with the dark brassy sounds of a Bach Stradivarius trumpet.
Fly fishing and chasing after big game with projectile weapons.
