Peer-Reviewed Publications
2024
55. Taming Molecular Folding: Anion-Templated Foldamers with Tunable Quaternary Structures. Eric A. John, Asia Marie S. Riel, Lianne H. E. Wieske, Debmalya Ray, Daniel A. Decato, Madeleine Boller, Zoltan Takacs, Máté Erdélyi, Vyacheslav S. Bryantsev, and Orion B. Berryman. Journal of the American Chemical Society 2024 146 (24), 16419-16427 DOI
2023
54. 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
53. 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. https://doi.org/10.1039/D3SC02348F
2022
52. Decato, D.A.; Sun, J.; Bollera, M.R.; Berryman, O.B. Pushing the limits of the hydrogen bond enhanced halogen bond—The case of the C–H hydrogen bond. Chem. Sci. 2022, 13, 11156–11162. https://doi.org/10.1039/D2SC03792K
51. 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. https://pubs.rsc.org/en/content/articlelanding/2022/CC/D1CC05475A
2021
50. 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. https://pubs.rsc.org/en/content/articlelanding/2021/cc/d1cc01827b#!divAbstract
49. Decato, D.A.; Riel, A.M.S.; May, J.H.; Bryantsev, V.S.; Berryman, O.B.; "Theoretical, Solid-Sate, and Solution Quantification of the Hydrogen Bond-Enhanced Halogen Bond." Angewandte Chemie International Edition 2021, 60,3685–3692 DOI</p
2020
48. 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. https://doi.org/10.1246/bcsj.20200274
47. John, E.A.‡; Massena, C.J.‡; Berryman, O.B. "Helical Anion Foldamers in Solution." Chemical Reviews 2020, 120, 5, 2783-2810 DOI
‡Both authors contributed equally.
2019
46. 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.
45. 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. https://doi.org/10.1107/S2052520618017778
44. 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. DOI
43. 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 (10), 2870–2880. DOI
42. 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, DOI
Invited article for the themed collection: In celebration of Julius Rebek’s 75th birthday!
2018
41. Massena, C. J.; Decato, D. A.; Berryman, O. B. "A Long‐Lived Halogen‐Bonding Anion Triple Helicate Accommodates Rapid Guest Exchange." Angewandte Chemie International Edition, 2018, 57, 16109–16113. DOI
40. Decato, D. A.; Berryman, O. B.*; “Simultaneous Halogen and Hydrogen Bonding to Carbonyl and Thiocarbonyl Functionality.” In: Multi-component Crystals: Synthesis, Concepts and Function, Tiekink, E.R. T. and Zukerman-Schpector, J. (eds) 2018, vol. 1, pp. 272-288, De Gruyter Publishers
39. 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. DOI
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. DOI
‡Both authors contributed equally.
37. 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. DOI
2017
36. 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. DOI
‡Both authors contributed equally.
35. Riel, A. M. S.; Wageling, N. B.; Decato, D. A.; Berryman, O. B.* “Anion-Arene Interactions and the Anionπ Phenomenon.” In: Comprehensive Supramolecular Chemistry II, Atwood, J. L., (ed.) 2017, vol. 1, pp.149-184. Oxford: Elsevier
2016
34. Massena, C. J.; Wageling, N. B.; Decato, D. A.; Martin Rodriguez, E.; Rose, A. M.; Berryman, O. B. "A Halogen-Bond-Induced Triple Helicate Encapsulates Iodide." Angewandte Chemie International Edition, 2016, 55, 12398–12402. DOI
Front-cover artwork, featured by SciShow.
33. 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. DOI
‡Both authors contributed equally, front cover artwork.
32. Tresca, B. W.; Berryman, O. B.; Zakharov, L. N.; Johnson, D. W.; Haley, M. M. "Anion-Directed Self-Assembly of 2,6-Bis(2-anilinoethynyl)pyridine Bis(amide) Scaffold." Supramolecular Chemistry, 2016, 28, 37–44. DOI
Invited for special issue in honor of Jonathan L. Sessler.
2015
31. 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, 2015, 16, 974–980. DOI
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. DOI
29. 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. DOI
28. 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. DOI
‡Both authors contributed equally, cover artwork.
2013
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. DOI
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. DOI
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. DOI
2012
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. DOI
2011
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. DOI
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. DOI
21. Berryman, O. B.; Dube, H.; Rebek, J. Jr. "Photophysics Applied to Cavitands and Capsules." Israel Journal of Chemistry, 2011, 51, 700–709. DOI
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. DOI
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. DOI
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. DOI
17. Berryman, O. B.; Sather, A. C.; Rebek, J. Jr. "A Light Controlled Cavitand Wall Regulates Guest Binding." Chemical Communications, 2011, 47, 656–658. DOI
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. DOI
2010
15. Sather, A. C.; Berryman, O. B.; Rebek, J. Jr. "Recognition and Extraction of the Uranyl Ion." Journal of the American Chemical Society, 2010, 132, 13572–13574. DOI
14. Beer, S.‡; Berryman, O. B.‡; Ajami, D.; Rebek, J. Jr. "Encapsulation of the Uranyl Dication." Chemical Science, 2010, 1, 43–47. DOI
- ‡Both authors contributed equally, front-cover artwork, featured in RSC press release, UK's Daily Telegraph, MSN news, Yahoo News, and AOL news.
2009
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. DOI
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. DOI
11. Berryman, O. B.; Johnson, D. W. "Experimental Evidence of Interactions Between Anions and Electron-Deficient Aromatic Rings." Chemical Communications, 2009, 3143–3153. DOI
- Invited feature article, cover artwork.
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. DOI
2008
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. DOI
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. DOI
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. DOI
2007
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. DOI
- Cited 269 times.
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. DOI
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. DOI
2006
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. DOI
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. DO
2005
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. DOI
Book Chapters
Decato, D. A.; Berryman, O. B.; "Simultaneous halogen and hydrogen bonding to carbonyl and thiocarbonyl functionality." Aspects of Multi-Component Crystals: Synthesis, Concepts and Function. Tiekink, E. R. T., Eds; De Gruyter Publishing, 2017, accepted.
Riel, A. M. S.‡; Wageling, N. B.‡; Decato, D. A.‡; Berryman, O. B. “In Comprehensive Supramolecular Chemistry II: Anion-Arene Interactions and the Anion-π Phenomenon.” Atwood, J., Gokel, G., Barbour, L., Eds.; Elsevier Publishers, 2016, published online. DOI
All authors contributed equally, invited book chapter.
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. Bottom-up Nanofabrication chapter
Patents
Berryman, O. B.; Massena, C. J. US Pat. Application # 62/362,226, 2016.
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.
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.