Concerted Halogen-Bonded Networks with N-Alkyl Ammonium Resorcinarene Bromides: From Dimeric Dumbbell to Capsular Architectures
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
Published inJournal of the American Chemical Society
© 2015 American Chemical Society
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.
PublisherAmerican Chemical Society
Publication in research information system
MetadataShow full item record
Related funder(s)Academy of Finland
Funding program(s)Research post as Academy Professor, AoF
Additional information about fundingN.K.B., F.P., and K.R. gratefully acknowledge the Academy of Finland (N.K.B.: grant no. 258653, K.R.,: grant nos. 263256 and 265328) and the University of Jyvaskyla for financial support.
Showing items with similar title or keywords.
Surprising solvent-induced structural rearrangements in large [N⋯I+⋯N] halogen-bonded supramolecular capsules : an ion mobility-mass spectrometry study Warzok, Ulrike; Marianski, Mateusz; Hoffmann, Waldemar; Turunen, Lotta; Rissanen, Kari; Pagel, Kevin; Schalley, Christoph A. (Royal Society of Chemistry, 2018)Coordinative halogen bonds have recently gained interest for the assembly of supramolecular capsules. Ion mobility-mass spectrometry and theoretical calculations now reveal the well-defined gas-phase structures of dimeric ...
Halogen bonding and host-guest chemistry between N-alkylammonium resorcinarene halides, diiodoperfluorobutane and neutral guests Pan, Fangfang; Dashti, Mohadeseh; Reynolds, Michael R.; Rissanen, Kari; Trant, John F.; Beyeh, Ngong Kodiah (Beilstein : Institut zur Foerderung der Chemischen Wissenschaften, 2019)Single crystal X-ray structures of halogen-bonded assemblies formed between host N-hexylammonium resorcinarene bromide (1) or N-cyclohexylammonium resorcinarene chloride (2), and 1,4-diiodooctafluorobutane and accompanying ...
The Effect of Halogen Bonding on the Packing of Bromine Substituted Pyridine and Benzyl Functionalized Resorcinarene Tetrapodands in the Solid State Tero, Tiia-Riikka; Salorinne, Kirsi; Nissinen, Maija (RSC publishing, 2012)The synthesis and characterization of new bromine-substituted pyridine and benzyl functionalized tetramethoxy resorcinarene tetrapodands are described and their solid-state structural properties and interactions were studied ...
Solid state halogen bonded networks vs. dynamic assemblies in solution: explaining N⋯X interactions of multivalent building blocks Tero, Tiia-Riikka; Salorinne, Kirsi; Malola, Sami; Häkkinen, Hannu; Nissinen, Maija (Royal Society of Chemistry, 2015)Tetrapyridine functionalized resorcinarene macrocycles were used as multivalent building blocks for the construction of halogen bonded networks with aryl halide linkers. In the solid state, resorcinarene macrocycles and ...
Halogen-Bonded Co-Crystals of Aromatic N-oxides : Polydentate Acceptors for Halogen and Hydrogen Bonds Puttreddy, Rakesh; Topic, Filip; Valkonen, Arto; Rissanen, Kari (MDPI AG, 2017)The C-ethyl-2-methylresorcinarene (1) forms 1:1 in-cavity complexes with aromatic N,N′-dioxides, only if each of the aromatic rings has an N−O group. The structurally different C-shaped 2,2′-bipyridine N,N′-dioxide ...