A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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-tekijät tai -toimittajat

Julkaisun tiedot

Julkaisun kaikki tekijät tai toimittajat: Twum, Kwaku; Truong, Khai-Nghi; Osei, Frank Boateng; von Essen, Carolina; Nadimi, Sanaz; Trant, John F.; Rissanen, Kari; Beyeh, Ngong Kodiah

Lehti tai sarja: Crystal Growth and Design

ISSN: 1528-7483

eISSN: 1528-7505

Julkaisuvuosi: 2023

Ilmestymispäivä: 01.07.2022

Volyymi: 23

Lehden numero: 2

Artikkelin sivunumerot: 1281-1287

Kustantaja: American Chemical Society (ACS)

Julkaisumaa: Yhdysvallat (USA)

Julkaisun kieli: englanti

DOI: https://doi.org/10.1021/acs.cgd.2c00325

Julkaisun avoin saatavuus: Ei avoin

Julkaisukanavan avoin saatavuus:

Tiivistelmä

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.

YSO-asiasanat: orgaaniset yhdisteet; nanoputket; halogeenit; orgaaninen kemia

Vapaat asiasanat: host-guest complexes

Liittyvät organisaatiot

Hankkeet, joissa julkaisu on tehty

OKM-raportointi: Kyllä

Raportointivuosi: 2022

Alustava JUFO-taso: 2