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Halo-methylphenyl substituted neutral tripodal receptors for cation-assisted encapsulation of anionic guests of varied dimensionality

Abstract

The aromatic tripodal anion receptors derived from either flexible [tris(2-aminoethyl)-amine], tren skeleton or any other benzene based rigid platforms reported from the beginning of the anion recognition chemistry, contain either electron-withdrawing group/s, or electron-donating group/s or zero substituents at the terminal aromatic rings. In this report, we have rationally designed and synthesized two tren based halo-methylphenyl disubstituted tris-urea receptors, which encompass one electron-withdrawing halide group (chloro/bromo) as well as one electron-donating methyl group at their terminal aromatic rings. The tris([(3-chloro-4-methylphenyl)amino]ethyl)-urea receptor, L1 efficiently captures spherical chloride and bromide anions in complexes 1a and 1b respectively via 1:1 cation-sealed host-guest encapsulation, whereas its isomeric tris([(4-Bromo-3-methylphenyl)amino]ethyl)-urea receptor, L2 encapsulates the smallest halide anion in complex 2a via formation of unimolecular polymeric host-guest assemblies. In contrary, the planar carbonate, tetrahedral sulphate and octahedral hexafluorosilicate anions of varied dimensionalities are engulfed inside the dimeric capsular cages of either of the isomeric neutral receptors L1 or L2 in 2:1 host-guest fashion, irrespective of the size of the countercations in complexes 1c, 1d, 2b or 2c.

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Publication details

The article was received on 29 May 2018, accepted on 05 Jul 2018 and first published on 05 Jul 2018


Article type: Paper
DOI: 10.1039/C8CE00885J
Citation: CrystEngComm, 2018, Accepted Manuscript
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    Halo-methylphenyl substituted neutral tripodal receptors for cation-assisted encapsulation of anionic guests of varied dimensionality

    G. Das and U. Manna, CrystEngComm, 2018, Accepted Manuscript , DOI: 10.1039/C8CE00885J

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