Publications

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Books and Book Chapters

1. N. K. Beyeh, K. Rissanen, 2016, pp 255-284
Type: chapters
Book: Calixarenes and Beyond
Chapter: N-Alkyl Ammonium Resorcinarene Salts: A Versatile Family of Calixarene-Related Host Molecules
Editors: Placido Neri, Jonathan L. Sessler, Mei-Xiang Wang,
ISBN: 978-3-319-31865-3 (Print) 978-3-319-31867-7

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Peer-Reviewed Publications (OU students in bold italics)

2023

69. Repurposing host-guest chemistry to suppress virulence and eradicate biofilms in multidrug resistant Pseudomonas aeruginosa and Acinetobacter baumannii

Jongerkouw, C.; Beyeh, N. K.; Osmekhina, E.; Leskinen, K.; Taimoory, S. M.; Federov, D.; Anaya-Plaza, E.; Kostiainen, M. A.; Trant, J. F.; Ras, R.; Saavalainen, P.; Linder, M.; Nature Communications, 2023, 14, 2141. https://rdcu.be/c9U2U

68. Reply to Where is the Macrocycle? Comment on “Simultaneous Organic and Inorganic Host-Guest Chemistry within Pillararene-Protein Cage Frameworks”

Shaukat, A.; Anaya-Plaza, E.; Beyeh, N. K.; Kostiainen, M. A., Chemistry – A European Journal, 2023, https://doi.org/10.1002/chem.202202022.

67. The “nitrogen effect”: Complexation with macrocycles potentiates fused heterocycles to form halogen bonds in competitive solvents

Twum, K.; Nadimi, S.; Osei, F. B.; Puttreddy, R.; Ojong, Y. B.; Hayward, J. J.; Rissanen, K.; Trant, J. F.; Beyeh, N. K. Chemistry, An Asian Journal, 2023, 18(6), e202201308

66. Resorcinarene cages: a new class of potential ¹²⁹Xe biosensors with unique chemical shift and exchange dynamics

Komulainen,A.; Fernando, P. U. A. I.; Mareš, J.; Selent, A.; Khalili, R.; Cesana, P. T.;  Ebeling, A.; Kantola, A, M.; Beyeh, N. K., Rissanen, K.; DeBoef, B.; Lantto, P.; Telkki, V-V. Cell Reports Physical Science, 2023, 4(2), 101281

65. Guest-mediated self-assembly of deprotonated 2-bromoresorcinarenes

Twum, K.; Truong, K-N.; Osei, F. B.; von Essen, C.; Nadimi, S.; Trant, J. F.; Rissanen, K.; Beyeh, N. K. Crystal Growth & Design, 2023, 23 (2), 1281-1287.

2022

64. Divalent Benzimidazolium-Based Axles for Self-Reporting Pseudorotaxanes

Taimoory S. M.; Yu, X.; Beyeh, N. K.; Nasri, S.; Trant, J. F. Journal of Organic Chemistry, 2022, 87, 23, 15783–15795

63. Naphthalene-Functionalized Resorcinarene as Selective, Fluorescent Self-Quenching Sensor for Kynurenic Acid

Karle, A.; Twum, K.; Sabbagh, N.; Haddad, A.; Taimoory, S. M.; Szczęśniak, M. M.; Evan Trivedi, E.; Trant, J. F.; Beyeh, N. K. Analyst, 2022, 147, 2264-2271.

62. Simultaneous Organic and Inorganic Host-Guest Chemistry within Pillararene-Protein Cage Frameworks

Shaukat, A.; Anaya-Plaza, E.; Beyeh, N. K.; Kostiainen, M. A.*, Chemistry – A European Journal, 2022, 28(11), e202200342. Hot Paper https://doi.org/10.1002/chem.202104341

61. Sharing the salt bowl: Counterion identity drives N-alkyl resorcinarene affinity for pyrophosphate in water

Twum, K.; Sadraei, S. I.; Feder, J.; Taimoory, S. M.*; Rissanen, K.*; Trant, J. F.*; Beyeh, N. K.* Organic Chemistry Frontiers, 2022, 9, 1267-1275. DOI: 10.1039/D1QO01877A

2021

60. Functionalized resorcinarenes effectively disrupt the aggregation of αA66−80 crystallin peptide related to cataracts

Twum, K.;  Bhattacharjee, A.; Laryea, E. T.; Esposto, J.; Omolloh, G.; Mortensen, S.; Jaradi, M.; Stock, N. L.; Schileru, N.; Elias, B.; Pszenica, E.; McCormick, T. M.; Martic, S.*; Beyeh, N. K.* RSC Medicinal Chemistry 2021, 12, 2022-2030. https://doi.org/10.1039/D1MD00294E

59. Recent Advances in Halogen Bonded Assemblies with Resorcin[4]arenes

Twum, K.*;  Rissanen, K.*; Beyeh, N. K.* The Chemical Record 2021, 20(2), 386-395. https://onlinelibrary.wiley.com/doi/10.1002/tcr.202000140

2020

58. Water Soluble Host-Guest Chemistry Involving Aromatic N-oxides and Sulfonateresorcinarene

Twum, K.; Schileru, N.; Elias, B.; Feder, J.; Yaqoo, L.; Puttreddy, R.; Szczesniak, M. M.; Beyeh, N. K.* Symmetry 2020, 12(11), 1751. https://doi.org/10.3390/sym12111751

57. Bringing a Molecular Plus One: Synergistic Binding Creates Guest-Mediated Three-Component Complexes

Taimoory, S. M.; Twum, K.; Dashti, M.; Pan, F.; Lahtinen, M.; Rissanen, K.;* Puttreddy, R.;* Trant, J. F.;* Beyeh, N. K.* J. Org. Chem. 2020, 85, 9, 5884–5894. Cover page. https://doi.org/10.1021/acs.joc.0c00220

56. Host-Guest Interactions of Sodiumsulfonatomethyleneresorcinarene and Quaternary Ammonium Halides: An Experimental-Computational Analysis of the Guest Inclusion Properties

Twum, K.; Rautiainen, J. M.; Yu, S.; Truong, K-N.; Feder, J.; Rissanen, K.; Puttreddy, R.*; Beyeh, N. K.*. Cryst. Growth & Des., 2020, 20, 4, 2367-2376. Cover page. https://doi.org/10.1021/acs.cgd.9b01540

2019

55. Thermodynamically driven Self-assembly of Pyridinearene to Hexameric Capsules

Kiesilä, A.; Beyeh, N. K., Moilanen, J. O.; Puttreddy, R.; Götz, S.; Rissanen, K.; Barran, P.; Lützen, A.; Kalenius, E.*  Org. Biomol. Chem. 2019, 17, 6980-6984. DOI:10.1039/C9OB01383K

54. Halogen bond mediated self-assembly of polymer-resorcinarene complexes

Välimäki, S.;  Gustavsson, L.; Beyeh, N. K.* Linko, V.; Kostiainen, M. A.* Macromol. Rapid Commun. 2019, 40, 190015. https://doi.org/10.1002/marc.201900158

53. Halogen bonding and host-guest chemistry between  N-alkyl ammonium resorcinarene halides, diiodoperfluorobutane and neutral guests

Pan, F.;* Pour, M. D. N.; Reynolds, M. R.; Rissanen, K.; Trant, J. F.;* Beyeh, N. K.* Beilstein J. Org. Chem. 2019, 15, 947–954. doi:10.3762/bjoc.15.91 

2018

52. Crystalline Cyclophane–Protein Cage Frameworks

Beyeh, N. K.; Nonappa, Liljeström, V.; Mikkilä, J.; Korpi, A.; Bochicchio, D.; Pavan, G. M.; Ikkala, O.; Ras, R. H. A.; Kostiainen, M. A.* ACS Nano, 2018, 12, 8029–8036. Link

51. Supramolecular Host-Guest Complex for Heparin Binding and Sensing

Välimäki, S.; Beyeh, N. K.; Linko, V.; Ras, R. H. A.; Kostiainen, M. A.* Nanoscale, 2018, 10, 14022-14030. Link

50. Host-Guest Complexes of Conformationally Flexible C-hexyl-2-Bromoresorcinarene and Aromatic N-oxides: Solid-state, Solution and Computational Studies

Puttreddy, R.; Beyeh, N. K.; Taimoory, S. M.; Meister, D.; Trant, J. F.;* Rissanen, K.*  Beilstein J. Org. Chem., 2018,  14, 1723–1733. Link

Prior to OU

49. High-Affinity and Selective Detection of Pyrophosphate in Water by a Resorcinarene Salt Receptor

Beyeh, N. K.;* Díez, I.; Taimoory, S. M.; Meister, D.; Feig, A.; Trant, J. F.;* Ras, R. H. A.;* Rissanen, K.*  Chem. Sci., 2018, 9, 1358-1367. Link 
48. Bamboo-like Chained Cavities and Other Halogen-Bonded Complexes from Tetrahaloethynyl Cavitands with Simple Ditopic Halogen Bond Acceptors

Turunen, L.;  Pan, F.; Beyeh, N. K.;  Trant, J. F.; Ras, R. H. A.; Rissanen, K.*  Cryst. Growth Des., 2018, 18, 513–520. Link47. Self-Complementary Dimers of Oxalamide-Functionalized Resorcinarene Tetrabenzoxazines

Džolić, Z.; Beyeh, N. K.; Cetina, M.; Turunen, L.; Rissanen, K.*  Chem. – Asian J., 2018, 13, 164 – 169. Link46. Host-guest complexes of C-propyl-2-bromoresorcinarene with aromatic-N-oxides

Puttreddy, R.; Beyeh, N. K.; Jurcek, P.; Turunen, L.; Trant, J. F.; Ras, R. H. A.; Rissanen, K.* Supramol. Chem., 2018, 30, 445-454. Link

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2017

45. Halogen-Bonded Solvates of Tetrahaloethynyl Cavitands

Turunen, L.; Pan, F.;* Beyeh, N. K.;* Cetina, M.; Trant, J. F.; Ras, R. H. A.; Rissanen, K.* CrystEngComm, 2017, 19, 5223–5229.   Link
44. Simultaneous Endo- and Exo-Complex Formation of Pyridine[4]arene Dimer with Neutral and Anionic Guests

Kiesilä, A.; Kivijärvi, L.; Beyeh, N. K.; Moilanen, J.; Groessl, M.; Rothe, T.; Götz, S.; Topić, F.; Rissanen, K.; Lützen, A.;* Kalenius, E.*  Angew. Chem. Int. Ed., 2017, 56, 10942–10946.  Link
43. Endo-/Exo- and Halogen Bonded Complexes of Conformationally Rigid Cethyl-2-bromoresorcinarene and aromatic N-oxides

Puttreddy, R.; Beyeh, N. K.; Ras, R. H. A.; Trant, J. F.; Rissanen, K.*  CrystEngComm, 2017, 19, 4312–4320.  Link
42. The Recognition of Viologen Derivatives in Water by N-Alkyl Ammonium Resorcinarene Chlorides

Beyeh, N. K.;* Jo, H. H.; Kolesnichenko, I.; Pan, F.; Kalenius, E.: Anslyn, E. V.;* Ras, R. H. A.; Rissanen, K.*J. Org. Chem., 2017, 82, 5198–5203.  Link
41. Host-Guest Complexes of C-ethyl-2-Methylresorcinarene and Aromatic N,N´-Dioxides

Puttreddy, R.; Beyeh, N. K.; Ras, R. H. A.; Rissanen, K.*  ChemistryOpen, 2017, 6, 417–423.  Link

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2016
40. Guest-Induced Folding of the N-Benzyl substituents in an Ammonium Resorcinarene Chloride and the Formation of a Halogen-Bonded Dimer of Capsules

Pan, F.; Beyeh, N. K.;* Ras, R. H. A.; Rissanen, K.*  Cryst. Growth & Des., 2016, 16, 6729–6733.  Link

39. [N···I⁺···N] Halogen-Bonded Dimeric Capsules from Tetrakis(3-pyridyl)ethylenecavitands

Turunen, L.; Warzok, U.; Puttreddy, R.; Beyeh, N. K.; Schalley, C. A.; Rissanen, K.*  Angew. Chem. Int. Ed., 2016, 55, 14033-14036.  Link

38. N-Alkyl Ammonium Resorcinarene Chloride Receptors for Guest Binding in Aqueous Environment

Beyeh, N. K.;* Pan, F.; Ras, R. H. A.* Asian J. Org. Chem., 2016, 5, 1027-1032.  Link37. N-Alkyl Ammonium Resorcinarene Polyiodides

Pan, F.; Beyeh, N. K.;* Ras, R. H. A.; Rissanen, K.* CrystEngComm, 2016, 18, 5724-5727.  Link36. 2-Methylresorcinarene: A Very High Packing Coefficient in a Mono-anion Based Dimeric Capsule and the X-Ray Crystal Structure of the Tetra-anion

Puttreddy, R.; Beyeh, N. K.; Kalenius, E.; Ras, R. H. A.; Rissanen, K.* Chem. Commun., 2016, 52, 8115-8118.  Link35. Anion-Exchange Properties of Trifluoroacetate and Triflate Salts of N-Alkyl Ammonium Resorcinarenes

Pan, F.; Beyeh, N. K.;* Bertella, S.; Rissanen, K.*  Chem. Asian J., 2016, 11, 782-788.  Link

34. Conformational Changes in Cmethyl-Resorcinarene Pyridine N-oxide Inclusion Complexes in the Solid State

Puttreddy, R.; Beyeh, N. K.;* Rissanen, K.* CrystEngComm, 2016, 18, 4971-4976.  Link

33. N-Alkyl Ammonium Resorcinarene Salts as High-Affinity Tetravalent Chloride Receptors

Beyeh, N. K.;* Pan, F.; Bhowmik, S.; Mäkelä, T.; Ras, R. H. A.: Rissanen, K.* Chem. Eur. J., 2016, 22, 1355-1361.  Link

32. Inclusion Complexes of Cethyl-2-Methylresorcinarene and Pyridine N-oxides: Breaking C-I···-O-N+ Halogen Bond by Host-Guest Complexation

Puttreddy, R.; Beyeh, N. K.;* Rissanen, K.* CrystEngComm, 2016, 18, 793-799.  Link

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2015
31. Concerted Halogen Bonded Networks with N-Alkyl Ammonium Resorcinarene Bromides: From Dimeric Dumbbell to Capsular Architectures

Pan, F.; Beyeh, N. K.;* Rissanen, K.* J. Am. Chem. Soc., 2015, 137, 10406-10413.  Link

30. Dimeric Resorcinarene Salt Capsules with Very Tight Encapsulation of Anions and Guest Molecules

Pan, F.; Beyeh, N. K.;* Rissanen, K.* RSC Adv., 2015, 5, 57912-57916.  Link

29. Cooperative binding of divalent diamides by N-alkyl ammonium resorcinarene chlorides

Beyeh, N. K.; Ala-Korpi, A.; Pan, F.; Jo, H. H.; Anslyn, E. V.;* Rissanen, K.* Chem. Eur. J., 2015, 21, 9556-9562.  Link

28.  A Halogen-Bonded Dimeric Resorcinarene Capsule

Beyeh, N. K.;* Pan, F.; Rissanen, K.* Angew. Chem. Int. Ed., 2015, 54, 7303-7307.  Link

27. Methylresorcinarene: A Reaction Vessel to Control the Coordination Geometry of Copper(II) in Pyridine N-oxide Copper(II) Complexes

Beyeh, N. K.;* Puttreddy, R.  Dalton Trans., 2015, 44, 9881-9886.  Link26. Aromatic N-oxides template open inclusion and dimeric capsular assemblies with methylresorcinarene

Beyeh, N. K.;* Puttreddy, R.; Rissanen, K.* RSC Adv., 2015, 5, 30222-30226.  Link

25. N-Alkyl ammonium resorcinarene salts: Multivalent halogen bonded deep cavity cavitands

Beyeh, N. K.;* Valkonen, A.; Bhowmik, S.; Pan, F.; Rissanen, K.* Org. Chem. Front., 2015, 2, 340-345.  Link

24. Encapsulation of secondary and tertiary ammonium salts by resorcinarenes and pyrogallarenes: The effect of size and charge concentration

Beyeh, N. K.;* Pan, F.; Valkonen, A.; Rissanen, K.* CrystEngComm, 2015, 17, 1181-1188.  Link

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2014 
23. Recognition of N-Alkyl- and N-Aryl-Acetamides by N-Alkyl Ammonium Resorcinarene Chlorides

Beyeh, N. K.;* Ala-Korpi, A.; Cetina, M.; Valkonen, A.; Rissanen, K.* Chem. Eur. J., 2014, 15144-15150  Link

22. Hierarchical ordering in a ternary co-crystals of C60, N-benzyl ammonium resorcinarene bromide and solvent molecules

Beyeh, N. K.; Pan, F.; Rissanen, K.* Cryst. Growth & Des., 2014, 14, 6161–6165.  Link

21. Tetraiodoethynyl resorcinarene cavitands as multivalent halogen bond donors

Turunen, L.; Beyeh, N. K.; Pan, F.; Rissanen, K.* Chem. Commun., 2014, 15920-15923.  Link

20. Halogen Bonded Analogues of Deep Cavity Cavitands

Beyeh, N. K.;* Cetina, M.; Rissanen, K.* Chem. Commun., 2014, 50, 1959-1961.  Link

19. Deprotonation of Resorcinarenes by Mono- and Diamine Bases: Complexation and Intermolecular Interactions in the Solid State

Beyeh, N. K.; Valkonen, A.; Rissanen, K.* CrystEngComm 2014, 16, 3758-3764.  Link

18. The synergetic interplay of weak interactions in the ion pair recognition of quaternary and diquaternary ammonium salts by halogenated resorcinarenes

Beyeh, N. K.; Göth, M.; Kaufmann, L.; Schalley, C. A.;* Rissanen, K.* Eur. J. Org. Chem., 2014, 80-85.  Link

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2013 
17. Complexation of Enantiomerically Pure Tetraalkylammonium Cations by Ethyl Resorcinarene

Beyeh, N. K.; Rissanen, K.* Supramol. Chem., 2013, 609-614.  Link

16. Size-selective Encapsulation of Hydrophobic Guests by Self-Assembled M4L6 Cobalt and Nickel Cages

Ronson, T. K.; Giri, C.; Beyeh, N. K.; Minkkinen, A.; Topić, F.; Holstein, J. J.; Rissanen, K;* Nitschke, J. R.* Chem. Eur. J., 2013, 19, 3374–3382.  Link

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2012
15. Binding Modes of Non-Spherical Anions to N-alkylammonium Resorcinarenes in the Solid State

Beyeh, N. K.; Cetina, M.; Rissanen, K.* Cryst. Growth & Des., 2012, 12, 4919–4926.  Link

14. Ion Pair Recognition of Tetramethyl Ammonium Salts by Halogenated Resorcinarenes

Beyeh, N. K.; Weimann, D. P.; Kaufmann, L.; Schalley, C. A.;* Rissanen, K.* Chem. Eur. J., 2012, 18, 5552–5557.  Link

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2011 
13. Dimeric Resorcin[4]arene Capsules in the Solid State

Beyeh, N. K.; Rissanen, K.* Isr. J. Chem., 2011, 51, 769–780.  Link

12. The inherent structural instability: concentration-dependent transformation of pyrogallarene to pyrogallarene lactones

Kalenius, E.;* Beyeh, N. K.; Jänis, J.; Rissanen, K.* Chem. Commun., 2011, 47, 2649–2651.  Link

11. Gas-phase H/D-exchange reactions on resorcinarene and pyrogallarene capsules: Proton transport through a one-dimensional Grotthuss mechanism

Winkler, H. D. F.; Dzyuba, E. V.; Sklorz, J. A. W.; Beyeh, N. K.; Rissanen, K.; Schalley, C. A.* Chem. Sci., 2011, 2, 615–624.  Link

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2010 
10. Tri- and Tetra-urea Piperazine Cyclophanes: Synthesis and Complexation Studies of Pre-organized and Folded Receptor Molecules

Raatikainen, K.; Beyeh, N. K.; Rissanen, K.*  Chem. Eur. J., 2010, 16, 14554–14564.  Link

9. Hydrogen Bond Stabilized N-alkylammonium Resorcinarene Halide Cavitands

Beyeh, N. K.; Cetina, M.; Löfman, M.; Luostarinen, M.; Shivanyuk, A.; Rissanen, K.*  Supramol. Chem., 2010, 22, 737–750.  Link

8. Piperazine Bridged Resorcinarene Cages

Beyeh, N. K.; Valkonen, A.; Rissanen, K.* Org. Lett, 2010, 12, 1392–1395.  Link

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2009 
7. Tetranitroresorcin[4]arene: synthesis and structure of a new stereoisomer

Beyeh, N. K.; Rissanen, K.* Tetrahedron Lett., 2009, 50, 7369–7373.  Link

6. Encapsulation of Tetramethyl Phosphonium Cations

Beyeh, N. K.; Valkonen, A.; Rissanen, K.* Supramol. Chem., 2009, 21, 142–148.  Link

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2008 
5. An Unlockable-Relockable Iron Cage by Subcomponent Self-Assembly

Mal, P.; Schultz, D.; Beyeh, K.; Rissanen, K.; Nitschke, J. R.* Angew. Chem. Int. Ed., 2008, 47, 8297–8301.  Link

4. Size- and Structure-selective Noncovalent Recognition of Saccharides by Tetraethyl and Tetraphenyl Resorcinarenes in the Gas Phase

Kalenius, E.; Kekäläinen, T.; Neitola, R.; Beyeh, K.; Rissanen, K.; Vainiotalo, P.* Chem. Eur. J., 2008, 14, 5220–5228.  Link

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2007 
3. Dansylated Resorcinarenes

Beyeh, N. K.; Aumanen, J.; Åhman, A.; Luostarinen, M.; Mansikkamäki, H.; Nissinen, M.; Korppi-Tommola, J.* Rissanen, K.* New J. Chem., 2007, 31, 370–376.  Link

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2006 
2. Synthesis of Chiral Resorcinarene-based Hosts and a Mass Spectrometric Study of their Chemistry in Solution and the Gas Phase

Beyeh, N. K.; Fehér, D.; Luostarinen, M.; Schalley, C. A.;* Rissanen, K.* J. Incl. Phenom. Macrocycl. Chem., 2006, 56, 381–394.  Link

1. Flying Capsules: Mass Spectrometric Detection of Pyrogallarene and Resorcinarene Hexamers

Beyeh, N. K.; Kogej, M.; Åhman, A.; Rissanen, K;* Schalley, C. A.* Angew. Chem. Int. Ed., 2006, 45, 5214–5218.  Link

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Patents

1. Jonkergouw, C.; Beyeh, N. K.; Osmekhina, E.; Ras, R.; Linder, M. Macrocyclic compounds and uses thereof.

AU2019359430A1; BR112021006569A2; CA3115432A1; CN113164412A; EP3863613A1; FI20185841A1; US2022008364A1; WO2020074776A1.