A1 Journal article (refereed)
Guest-Mediated Self-Assembly of Deprotonated 2-Bromoresorcinarenes (2023)
Twum, K., Truong, K.-N., Osei, F. B., von Essen, C., Nadimi, S., Trant, J. F., Rissanen, K., & Beyeh, N. K. (2023). Guest-Mediated Self-Assembly of Deprotonated 2-Bromoresorcinarenes. Crystal Growth and Design, 23(2), 1281-1287. https://doi.org/10.1021/acs.cgd.2c00325
JYU authors or editors
Publication details
All authors or editors: Twum, Kwaku; Truong, Khai-Nghi; Osei, Frank Boateng; von Essen, Carolina; Nadimi, Sanaz; Trant, John F.; Rissanen, Kari; Beyeh, Ngong Kodiah
Journal or series: Crystal Growth and Design
ISSN: 1528-7483
eISSN: 1528-7505
Publication year: 2023
Publication date: 01/07/2022
Volume: 23
Issue number: 2
Pages range: 1281-1287
Publisher: American Chemical Society (ACS)
Publication country: United States
Publication language: English
DOI: https://doi.org/10.1021/acs.cgd.2c00325
Publication open access: Not open
Publication channel open access:
Abstract
Doubly and triply deprotonated 2-bromo-C-alkylresorcinarene anions form host–guest complexes with both tetramethylammonium cations and bis-protonated dimethyl piperazine cations. The trianion forms a fully closed dimeric capsule with one endo- and two exo-cavity bis-protonated dimethyl piperazine cations. Interestingly, the dianion crystallized from a mixture of the 2-bromo-C-methylresorcinarene, dimethylethylenediamine, and tetramethylammonium chloride forms a nanotube consisting of only the 2-bromo-C-methylresorcinarene anion and the tetramethylammonioum cation. The nanotube has an exo-functionalized anionic hydrophilic outer surface that interacts with cationic guests and a hydrophobic interior channel. Solution studies support the deprotonation and the formation of these host–guest complexes. Quantification of binding in chloroform shows a very strong binding constant between the 2-bromo-C-pentylresorcinarene and tetramethylammonium chloride (K1 = 3.63 × 105 M–1, K2 = 2.32 × 104 M–1), far higher than that observed for the unfunctionalized C-pentylresorcinarene (K1 = 5.10 × 104 M–1, K2 = 1.30 × 103 M–1). We attribute this to the stronger ion-pair in the former as the halogen increases the acidity of the phenolic hydroxyl groups.
Keywords: organic compounds; nanotubes; halogens; organic chemistry
Free keywords: host-guest complexes
Contributing organizations
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Ministry reporting: Yes
Reporting Year: 2023
Preliminary JUFO rating: 2