Concerted Halogen-Bonded Networks with N-Alkyl Ammonium Resorcinarene Bromides: From Dimeric Dumbbell to Capsular Architectures

Fangfang Pan, Ngong Kodiah Beyeh, Kari Rissanen

Research output: Contribution to journalArticleScientificpeer-review

28 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)10406–10413
JournalJournal of the American Chemical Society
Volume137
Issue number32
DOIs
Publication statusPublished - Jul 2015
MoE publication typeA1 Journal article-refereed

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