Guest-Induced Folding of the N-Benzyl Substituents in an Ammonium Resorcinarene Chloride and the Formation of a Halogen-Bonded Dimer of Capsules

Research output: Contribution to journalArticleScientificpeer-review

Researchers

  • Fangfang Pan
  • Ngong Kodiah Beyeh
  • Robin Ras

  • Kari Rissanen

Research units

  • Central China Normal University
  • University of Jyväskylä

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.

Details

Original languageEnglish
Pages (from-to)6729-6733
Number of pages5
JournalCrystal Growth and Design
Volume16
Issue number12
Publication statusPublished - 7 Dec 2016
MoE publication typeA1 Journal article-refereed

ID: 9819238