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


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Publication details

All authors or editorsTwum, Kwaku; Truong, Khai-Nghi; Osei, Frank Boateng; von Essen, Carolina; Nadimi, Sanaz; Trant, John F.; Rissanen, Kari; Beyeh, Ngong Kodiah

Journal or seriesCrystal Growth and Design

ISSN1528-7483

eISSN1528-7505

Publication year2023

Publication date01/07/2022

Volume23

Issue number2

Pages range1281-1287

PublisherAmerican Chemical Society (ACS)

Publication countryUnited States

Publication languageEnglish

DOIhttps://doi.org/10.1021/acs.cgd.2c00325

Publication open accessNot 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.


Keywordsorganic compoundsnanotubeshalogensorganic chemistry

Free keywordshost-guest complexes


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Ministry reportingYes

Reporting Year2023

Preliminary JUFO rating2


Last updated on 2024-10-03 at 17:16