A1 Journal article (refereed)
Concerted Halogen-Bonded Networks with N-Alkyl Ammonium Resorcinarene Bromides: From Dimeric Dumbbell to Capsular Architectures (2015)

Pan, F., Beyeh, N. K., & Rissanen, K. (2015). Concerted Halogen-Bonded Networks with N-Alkyl Ammonium Resorcinarene Bromides: From Dimeric Dumbbell to Capsular Architectures. Journal of the American Chemical Society, 137(32), 10406-10413. https://doi.org/10.1021/jacs.5b06590

JYU authors or editors

Pan, Fangfang
Beyeh, Ngong Kodiah
Rissanen, Kari

Publication details

All authors or editors: Pan, Fangfang; Beyeh, Ngong Kodiah; Rissanen, Kari

Journal or series: Journal of the American Chemical Society

ISSN: 0002-7863

eISSN: 1520-5126

Publication year: 2015

Volume: 137

Issue number: 32

Pages range: 10406-10413

Publisher: American Chemical Society

Publication country: United States

Publication language: English

DOI: https://doi.org/10.1021/jacs.5b06590

Publication open access: Openly available

Publication channel open access: Partially open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/71115

Abstract

N-Alkyl ammonium resorcinarene bromides and 1,4-diiodooctafluorobutane via multiple intermolecular halogen bonds (XB) form different exotic supramolecular architectures through subtle changes of the upper rim substituents. Dimeric dumbbell-like assembly with encapsulated guest molecules is generated with N-benzyl substituents. The N-hexyl groups engender an XB-induced polymeric pseudocapsule and an XB-induced dimeric capsule with entrapped 1,4-dioxane guest molecules. The N-propyl and N-cyclohexyl groups generate deep cavity cavitands. The deep cavity cavitands possess cavities for self-inclusion leading to polymeric herringbone arrangement in one direction and that pack into 3D polymeric arrangement resembling egg crate-like supramolecular networks. These assemblies are studied in solution via NMR spectroscopy and in the solid state via X-ray crystallography.

Keywords: supramolecular chemistry

Free keywords: halogen bonding

Fields of science: