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Study of the host–guest interaction between N,N′-bis[4-(dimethylaminophenyl)methyl]butane-1,4-diamine and the cucuribit[n]urils (n = 6, 7)

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Abstract

The interaction between the cucuribit[n]urils (Q[n]), where n = 6 or 7, and the guest N,N′-bis[4-(dimethylaminophenyl)methyl]butane-1,4-diamine (G) has been studied in aqueous solution by 1H NMR spectroscopy, electronic absorption spectroscopy and Isothermal Titration Calorimetry (ITC). In the case of Q[6], a 1 : 1 host–guest complex is favoured with one end of G initially embedded in the Q[6], although over time (48 h), the Q[6] shuttles along the chain such that it resides over the centre of G. For Q[7], a 2 : 1 host–guest complex is formed with the aromatic groups at each end of G buried in a Q[7] cavity. The molecular structure of the inclusion complex having an overall composition of Q[6]·GH2·2Cl·14H2O has been determined, and clearly shows the insertion of the guest molecule with the host Q[6] and it is localised therein by two N–H⋯O hydrogen bonds.

Graphical abstract: Study of the host–guest interaction between N,N′-bis[4-(dimethylaminophenyl)methyl]butane-1,4-diamine and the cucuribit[n]urils (n = 6, 7)

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Publication details

The article was received on 24 Jun 2019, accepted on 27 Aug 2019 and first published on 27 Aug 2019


Article type: Paper
DOI: 10.1039/C9NJ03254A
New J. Chem., 2019, Advance Article

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    Study of the host–guest interaction between N,N′-bis[4-(dimethylaminophenyl)methyl]butane-1,4-diamine and the cucuribit[n]urils (n = 6, 7)

    Z. Xiao, Y. Zhou, W. Xu, T. J. Prior, B. Bian, C. Redshaw, Z. Tao and X. Xiao, New J. Chem., 2019, Advance Article , DOI: 10.1039/C9NJ03254A

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