Publications

Peer-Reviewed Publications

2023

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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

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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

Graphical abstract: Pushing the limits of the hydrogen bond enhanced halogen bond—the case of the C–H hydrogen bond

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

Graphical abstract: Halogen bonding organocatalysis enhanced through intramolecular hydrogen bonds

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

Graphical abstract: Modulating photoswitch performance with halogen, coordinative and hydrogen bonding: a comparison of relative bond strengths

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   

hbexbdan

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

2020

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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

TOC Image Helical Anion Foldamer

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.

[Figure 1]

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

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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 20199, 522. DOI


Cover of HBeXB Journal

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


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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

TOC-cjm

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

Image of Multi-component Crystals Textbook

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


 
nick-2nd-pub

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


asia-hb-xb

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.


Jiuy's molecule

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

Picture of Asia's molecule binding oxygen and sulfur

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.

 
Cover of Supramolecular Chemistry 2 Textbook
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

Angewandte cover

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.


Nick's cover art

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.


Picture of Orion's molecule

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

Asia's molecule binding perrhenate

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


Dan's molecule

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


Orion's molecule binding halides and water

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


Chem comm cover

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
- Editor designated "hot paper."

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. DOI

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 onlineDOI
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.