A1 Journal article (refereed)
Guest-Induced Folding of the N-Benzyl Substituents in an Ammonium Resorcinarene Chloride and the Formation of a Halogen-Bonded Dimer of Capsules (2016)


Pan, F., Beyeh, N. K., Ras, R. H. A., & Rissanen, K. (2016). Guest-Induced Folding of the N-Benzyl Substituents in an Ammonium Resorcinarene Chloride and the Formation of a Halogen-Bonded Dimer of Capsules. Crystal Growth and Design, 16(12), 6729-6733. https://doi.org/10.1021/acs.cgd.6b01454


JYU authors or editors


Publication details

All authors or editors: Pan, Fangfang; Beyeh, Ngong Kodiah; Ras, Robin H. A.; Rissanen, Kari

Journal or series: Crystal Growth and Design

ISSN: 1528-7483

eISSN: 1528-7505

Publication year: 2016

Volume: 16

Issue number: 12

Pages range: 6729-6733

Publisher: American Chemical Society

Publication country: United States

Publication language: English

DOI: https://doi.org/10.1021/acs.cgd.6b01454

Publication open access: Not open

Publication channel open access:


Abstract

In methanol, N-benzyl ammonium resorcinarene chloride (Bn-NARCl) crystallizes as a solvate with the benzyl groups oriented in an open flower-like manner parallel to the cation–anion seam. 1,4-Dioxane as guest triggers a “semi-closed” single-molecule capsule with two benzyl “arms” enclosing the guest. The introduction of halogen bond (XB) donor 1,4-diiodoperfluorobutane (1,4-DIOFB) additionally folds the remaining two benzyl arms thus resulting in a fully closed capsule. Two 1,4-DIOFB molecules bridge two such Bn-NARCl capsules, forming a 2:2:2 XB held dimeric assembly of single-molecule capsules. The peculiar behavior was not observed in the bromide analog under similar experimental conditions. The studies were performed in solid state by X-ray single crystal crystallography, and MM level theoretical calculations.


Keywords: capsules

Free keywords: thermodynamically disfavored conformations; supramolecular self-assembly processes; halogen-bonded dimers


Contributing organizations


Related projects


Ministry reporting: Yes

Reporting Year: 2016

JUFO rating: 2


Last updated on 2021-18-06 at 18:51