TY - JOUR
T1 - An Investigation into Interactions between 1-Butyl-3-methyl-imidazolium Tetrafluoroborate Guest and Pillar[5]arene Hosts
T2 - An Experimental and Molecular Dynamics Approach
AU - Al Mamari, Hamad H.
AU - Al Harrasi, Iman
AU - Suliman, Fakhreldin O.
N1 - Publisher Copyright:
© 2021 Wiley-VCH GmbH
PY - 2021/1/8
Y1 - 2021/1/8
N2 - Various synthesized Pillar[5]arene macrocycles were allowed to form complexes with the ionic liquid; 1-Butyl-3-methyl-imidazolium tetrafluoroborate (IL). The pillar[5]arenes used in the study were synthesized by the established pioneering method of Ogoshi that involves treatment of 1,4-disubstituted benzenes with paraformaldehyde in the presence of BF3.OEt2. Selected synthesized pillar[5]arenes; DMpillar[5]arene (4a), DPpillar[5]arene (4b), DPGpillar[5]arene (4c) were allowed to form complexes with the ionic liquid, and complexations were confirmed by MALDI-TOF, ESI-MS, 1H NMR, and DOSY spectroscopy. ESI-MS reveals highly intense ion peaks that correspond to [pillar[5]arene+IL]+ for the complexes of the three pillar[5]arenes with the ionic liquid. Changes in characteristic peaks in hosts and guests, as a result of complexation, were studied by 1H NMR. Results obtained suggest a formation of 1 : 1 complexes between the pillar[5]arene host and the IL guest. Host-guest interactions in such complexes have also been studied using 1H-1H 2D ROESY NMR spectroscopy. Obtained through-space correlations revealed interactions between certain parts of the pillar[5]arene hosts and the ionic liquid. The complexation between the three pillar[5]arenes and the IL was studied by molecular dynamics (MD) simulations. The obtained results suggest the insertion of the IL inside the nanocavities of the hosts.
AB - Various synthesized Pillar[5]arene macrocycles were allowed to form complexes with the ionic liquid; 1-Butyl-3-methyl-imidazolium tetrafluoroborate (IL). The pillar[5]arenes used in the study were synthesized by the established pioneering method of Ogoshi that involves treatment of 1,4-disubstituted benzenes with paraformaldehyde in the presence of BF3.OEt2. Selected synthesized pillar[5]arenes; DMpillar[5]arene (4a), DPpillar[5]arene (4b), DPGpillar[5]arene (4c) were allowed to form complexes with the ionic liquid, and complexations were confirmed by MALDI-TOF, ESI-MS, 1H NMR, and DOSY spectroscopy. ESI-MS reveals highly intense ion peaks that correspond to [pillar[5]arene+IL]+ for the complexes of the three pillar[5]arenes with the ionic liquid. Changes in characteristic peaks in hosts and guests, as a result of complexation, were studied by 1H NMR. Results obtained suggest a formation of 1 : 1 complexes between the pillar[5]arene host and the IL guest. Host-guest interactions in such complexes have also been studied using 1H-1H 2D ROESY NMR spectroscopy. Obtained through-space correlations revealed interactions between certain parts of the pillar[5]arene hosts and the ionic liquid. The complexation between the three pillar[5]arenes and the IL was studied by molecular dynamics (MD) simulations. The obtained results suggest the insertion of the IL inside the nanocavities of the hosts.
KW - Host-Guest Chemistry
KW - Inclusion Complexes
KW - Ionic Liquids
KW - Macrocycles
KW - Pillar[5]arenes
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U2 - 10.1002/slct.202003241
DO - 10.1002/slct.202003241
M3 - Article
AN - SCOPUS:85098882009
SN - 2365-6549
VL - 6
SP - 82
EP - 89
JO - ChemistrySelect
JF - ChemistrySelect
IS - 1
ER -