ÁÔÆæÖØ¿Ú

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 ÁÔÆæÖØ¿Ú (UM) and is currently full professor. Orion also directs the Small Molecule X-ray Differaction Core facility at UM. Orion is a CoBRE investigator within the Center for Biomolecular Structure and Dynamics where he teaches and develops new catalysts and foldamers 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

Courses Taught

CHMY 223 Organic Chemistry II

CHMY 222 Organic Chemistry I Lab

CHMY 292 Independant Study

CHMY 411 Advanced Organic

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

Teaching Experience

CHMY 223 Organic Chemistry II

CHMY 222 Organic Chemistry Lab I

CHMY 411 Advanced Organic

CHMY 562 Organic Structure and Mechanism

CHMY 580 Supramolecular Research Survey

CHMY 595 Physical Organic Chemistry

CHMY 630 Departmental Seminar

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 creating foldamer molecules with higher-order helical structure and new organocatalysts. These molecules are applied 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, foldamers, self-assembly, ligand development, photoisomerization

Publications

PEER-REVIEWED PUBLICATIONS

54.      John, E. A.; Riel, A. M. S.; Wieske, L. H. E.; Ray, D.; Decato, D. A.; Boller, M.; Takacs, Z.; Erdelyi, M.; Bryantsev, V. S.*; Berryman, O. B.* “Taming Molecular Folding: Anion-Templated Foldamers with Tunable Quaternary Structures.” Journal of the American Chemical Society, 2024, 146, 16419-16427. https://doi.org/10.1021/jacs.3c14820

53.      Suating, P.; Kimberly, L. B.; Ewe, M. B.; Chang, S. L.; Fontenot, J. M.; Sultane, P. R.; Bielawski, C. W.; Decato, D. A.; Berryman, O. B.; Taylor, A. B.; Urbach, A. R. “Cucurbit[8]uril Binds Nonterminal Dipeptide Sites with High Affinity and Induces a Type II β-Turn.” Journal of the American Chemical Society, 2024, 146, 7649-7657.

52.      Sun, J.; Decato, D.A.; Bryantsev, V.S.; John, E.A.; Berryman, O. B.* The Interplay Between Hydrogen and Halogen Bonding: Substituent Effects and their Role in the Hydrogen Bond Enhanced Halogen Bond." Chemical Science, 2023, 14, 8924-8935. 

51.      Decato, D. A.*; Janke, M.†; Berryman, O. B.* “Conformational Polymorphism of 3-(azidomethyl)benzoic acid.” Acta Crystallographica Section C. 2023, 79, 344-352.

-† Denotes high school teacher co-author

50.      Decato, D. A.; Sun J.; Boller, M. R.†; Berryman, O. B.* “Pushing the Limits of the Hydrogen Bond Enhanced Halogen Bond—the Case of the C-H Hydrogen Bond.” Chemical Science, 2022, 13, 11156–11162.

49.      Riel, A. M. S.; Decato, D. A.; Sun J.; Berryman, O. B.* “Halogen Bonding Organocatalysis Enhanced Through Intramolecular Hydrogen Bonds.” Chemical Communications, 2022, 58, 1378–1381.

48.      Lindbald, S.; Sethio, D.; Berryman, O. B.*; Erdélyi, M.* "Modulating Photoswitch Performance with Halogen, Coordinative and Hydrogen Bonding: A Comparison of Relative Bond Strengths." Chemical Communications 2021, 57, 6261-6263.              

47.      Decato, D. A.; Riel, A. M. S.; May J. H.†; Bryantsev, V. S.; Berryman, O. B.* "Theoretical, Solid-State and Solution Quantification of the Hydrogen Bond Enhanced Halogen Bond." Angewandte Chemie, International Edition 2021, 60, 3685-3692.

                                          -† Denotes undergraduate co-author

46.      Turunen, L.; Németh, F. B.; Decato, D. A.; Pápai, P. I.; Berryman, O. B.*; Erdélyi, M.* "Halogen Bonds of Iodonium Ions: A World Dissimilar to Silver Coordination." Bulletin of the Chemical Society of Japan 2020, 94. 191-196.

45.      John, E. A.‡; Massena, C. J.‡; Berryman, O. B.* "Helical Anion Foldamers in Solution." Chemical Reviews 2020, 120, 5, 2783-2810.

- ‡ Both authors contributed equally

44.      Riel, A. M. S.; Huynh, H. T.; Jeannin, O.; Berryman, O. B.; Fourmigue, M.* “Organic Selenocyanates as Halide Receptors: From Chelation to One-Dimensional Systems.” Crystal Growth & Design 2019, 19, 1418-1425.

43.      Riel, A. M. S.; Jeannin, O.; Berryman, O. B.; Fourmigue, M.* “Co-crystals of an Organic Triselenocyanate with Ditopic Lewis Bases: Recurrent Chalcogen Bond Interactions Motifs.” Acta Crystallographica Section B 2019, B75, 34-38.

42.      Decato, D. A.; Riel, A. M. S.; Berryman, O. B.* "Anion Influence on the Packing of 1,3-Bis(4-Ethynyl-3-Iodopyridinium)-Benzene Halogen Bond Receptors." Crystals 2019, 9, 522-536.

41.      Riel, A. M. S.; Rowe, R. K.; Ho, E. N.; Carlsson, A.-C. C.; Rappé, A. K.; Berryman, O. B.*; Ho, P. S.* "Hydrogen Bond Enhanced Halogen Bonds: A Synergistic Interaction in Chemistry and Biochemistry." Accounts of Chemical Research 2019, 52, 2870–2880. 

40.      Decato, D. A.; Berryman, O. B.* "Structural and Computational Characterization of a Bridging Zwitterionic-Amidoxime Uranyl Complex." Organic Chemistry Frontiers, 2019, 6, 1038-1043, 2019. 

39.      Massena, C. J., Decato, D. A., Berryman, O. B.* “A Long-Lived Halogen-Bonding Anion Triple Helicate Accomodates Rapid Guest Exchange.” Angewandte Chemie, International Edition, 2018, 57, 16109-16113.           

38.      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.

-† Denotes undergraduate co-author    ‡ Both authors contributed equally

37.      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.  

36.      Sun, J.; Riel A. M. S.; Berryman, O. B. * “Solvatochromism and Fluorescence Response of a Halogen Bonding Anion Receptor.” New Journal of Chemistry, 2018, 42, 10489–10492.

- Invited contribution to thematic issue on halogen bonding

35. Riel, A. M. S.; Jessop, M. J.†; Decato, D. A.; Massena, C. J.; Nascimento, V. R.†; Berryman, O. B.* ”Experimental Investigation of Halogen-Bond Hard-Soft Acid Base Complementarity.” Acta Crystallographica Section B, 2017, B73, 203-209.

- Invited contribution to thematic issue on halogen bonding       -† Denotes undergraduate co-author

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, featured by NSF EPSCoR/IDeA Foundation, SciShow, ÁÔÆæÖØ¿Ú Associated Technology Rountables, ÁÔÆæÖØ¿Ún Magazine, UM President’s Report, UM We Are ÁÔÆæÖØ¿Ú tour, highlighted in Atlas of Science      -† Denotes undergraduate co-author

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.

-† Denotes undergraduate co-author     ‡ Both authors contributed equally

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.

                          -† Denotes undergraduate co-author

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, E71, 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, 2016, 28, 37-44. (invited for special issue in honor of Jonathan L. Sessler)

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 a rapidly evolving 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. “Selective Recognition and Extraction of the Uranyl Ion.” 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, cited 268 times, Web of Science 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. N.; O'Connor, M. J.; Haley, M. M. "Synthesis and Characterization of Pyridine- and Thiophene-Based Platinacyclyne." 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

1. Decato, D. A.; John, E. A. Berryman, O. B.*; “Halogen Bonding: An Introduction.” In: Huber, S. M., Ed Halogen Bonding in Solution; Wiley-VCH Publishers. 2021, vol. 1, pp 1-41.

B.    Riel, A. M. S.; Wageling, N. B.; Decato, D. A.; Berryman, O. B.* “Anion-Arene Interactions and the Anion-π Phenomenon.” In: Atwood, J. L., (ed.) Comprehensive Supramolecular Chemistry II, 2017, vol. 1, pp. 149-184. Oxford: Elsevier.

C.    Decato, D. A.; Berryman, O. B.*; “Simultaneous Halogen and Hydrogen Bonding to Carbonyl and Thiocarbonyl Functionality” in Aspects of Multi-component Crystals: Synthesis, Concepts and Function, 2018, vol. 1, pp272-288. Tiekink, E. R. T., Eds; De Gruyter Publishers.

D.   Rather Healey, E.; Vickaryous, W. J.; Berryman, O. B.; Johnson, D. W. “Self-Assembled Supramolecular Main Group Coordination Complexes” 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.; Palmer Christopher; “Stationary Phase Chromatography Methods and Compounds.” Filed February 7, 2022. Application No. 63307258.

II.    Lohrman, J.; Riel A. M. S.; Decato, D. A.; Haley, M.; Johnson, D. W.; Berryman, O. B.; “Fluorescent Halogen Bonding Arylethynyl Scaffolds for Anion Recognition.” filed May 1, 2019. U.S. Patent No. 16/401,037.

III.   Berryman, O. B.; Massena, C. J. “A Halogen-Bond-Induced Triple Helicate Encapsulates Iodide.” Serial No. 62/362,226, filed July 14, 2016.

IV. 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.

V. 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.

Affiliations

Center for Biomolecular Structure and Dynamics

ÁÔÆæÖØ¿Ú University System Materials Science Program

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

Honors / Awards

2023 NSF CHE DRP - How Charge, Sterics and HBeXB Influence Assembly of Higher-Order Helicates 

• Berryman, Lead P.I.

2023 NSF CHE DRP - Halogen Bonding Liquid Chromatography 

• Berryman, Co-P.I.

2022 Murdock Commercialization Initiation Project - Advancement of Halogen Bonding Liquid Chromatography to Commercialization

• Berryman, Co-P.I.

2021 NSF MSN DRP - Fundamental Studies of the Hydrogen Bond Enhanced Halogen Bond (HBeXB) for Molecular Folding and Anion Transport

• Berryman, Lead P.I.

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)                                                                                 

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.