Interaction of Inverted Cucurbit[7]uril with N,N'-dibenzyl -4,4'-pyridine Chloride†

doi:10.7503/cjcu20160458

Abstract

Abstract:

An inclusion complex formed on self-assembly of the inverted cucurbit[7]uril(iQ[7]) host with N,N'-dibenzyl-4,4'-pyridine chloride(G1) guest was investigated by ¹H NMR technique, electronic absorption and fluorescence spectroscopies, isothermal titration calorimetry(ITC) experiments and MALDI-TOF mass spectrometry. The experimental results showed that iQ[7] can encapsulate the benzyl moiety of the guest in its hydrophobic cavity to form dumbbell-type host-guest supramolecular assembly, and the inclusion ratio is 2:1. While a part of 4,4'-bipyridine is located inside the cavity of the iQ[7] host, the other part remains outside of the portal of the iQ[7] host.

Key words: Inverted cucurbit[7]uril, N,N'-dibenzyl-4,4'-pyridine chloride, Supramolecular self-assembly

CLC Number:

TrendMD:

GAO Zhongzheng, YANG Liguo, BAI Dong, CHEN Lixia, TAO Zhu, XIAO Xin. Interaction of Inverted Cucurbit[7]uril with N,N'-dibenzyl -4,4'-pyridine Chloride^†[J]. Chem. J. Chinese Universities, 2017, 38(2): 212.

Figures/Tables 6

Fig.1 Structures of the inverted cucurbit[7]uril (iQ[7])(A) and the guest G1(B)

Fig.2 1H NMR spectra(500 MHz, D2O) showing the interaction between G1 and iQ[7] at 20 ℃a. iQ[7]; b. n(iQ[7]):n(G1)=0.4; c. n(iQ[7]):n(G1)=0.9; d. n(iQ[7]):n(G1)=1.2; e. n(iQ[7]):n(G1)=2.0; f. G1.

Fig.3 COSY spectrum of G1 and iQ[7] with n(iQ[7])/n(G1)=1.2 in D2O at 20 ℃

Fig.4 Corrected heat rate(A) and normalized fit(B) for the complexation of iQ[7] and G1 in aqueous solution at 25 ℃

Fig.5 Absorption spectra(A) and fluorescence spectra(B) for G1(2.0×10-5 mol/L) with increasing the amount of iQ[7]Inset in (A) shows the absorbance vs. n(iQ[7])/n(G1) plot; inset in (B) shows the fluorescence vs. n(iQ[7])/n(G1) plot. n(iQ[7])/n(G1) from a to p: 0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.2, 2.4, 2.6, 2.8, 3.0.

Fig.6 Mode of binding interaction between G1 and iQ[7]

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