Supramolecular Self-assemblies of Cucurbit[7]uril with N,N'-Bis(4-dimethylaminobenzyl)-decane-1,10-diamine†

doi:10.7503/cjcu20140255

Abstract

Abstract:

Molecular motions are quite common in biosystems and closely related to macroscopic motions guest. In the present work, N,N'-bis(4-dimethylaminobenzyl)-decane-1,10-diamine(C10DA) with multiple binding sites was designed and synthesized, while the structures and interaction of cucurbit[7]uril with the guest were investigated by ¹H NMR technique, electronic absorption and fluorescence spectroscopies in details. The experimental results showed that cucurbit[7]uril can include C10DA forming a pseudorotaxane inclusion complexes or dumbbell-shaped inclusion complexes by changing the molar ratio of the host and guest. This observation contributes to a deeper understanding in molecular recognition, design and construction of novel molecular machines.

Key words: Cucurbit[n]uril, Pseudorotaxane, Dumbbell inclusion complex, Supramolecular self-assembly

CLC Number:

O641.3

TrendMD:

YANG Bo, WU Mingqiang, XIAO Xin, XUE Saifeng, TAO Zhu, WEI Gang. Supramolecular Self-assemblies of Cucurbit[7]uril with N,N'-Bis(4-dimethylaminobenzyl)-decane-1,10-diamine^†[J]. Chem. J. Chinese Universities, 2014, 35(11): 2442.

Figures/Tables 5

Fig.1 Structures of Q[7] and the guest C10DA

Scheme 1 Synthetic process for guest C10DA

Table 1 Chemical shifts of the protons of bound guests in Q[7]-C10DA with the free guest

Complex	Δδ
Complex	H_a	H_b	H_c	H_d	H_e	H_f	H_g	H_h
Free C10DA	3.17	7.53	4.14	2.91	1.52	1.12	1.12	1.12
n(Q[7])/n(C10DA)=0.7	No change	-0.08	-0.10	0.01	0.98	0.64	0.64	0.64
n(Q[7])/n(C10DA)=2.0	0.24	0.92	0.36	-0.23	-0.29	-0.25	-0.12	-0.12

Fig.2 Changes in UV absorption intensity of C10DA(0.20×10-5 mol/L) at λ=257 nm upon the titration of Q[7] in water (A) n(Q[7])/n(C10DA) from a to q: 0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.2, 1.4, 1.6, 1.8, 2.0, 2.2, 2.6, 2.8, 3.0, 3.4, 3.6; (B) A—n(Q[7])/n(C10DA) curve of Q[7]-C10DA system.

Fig.3 Changes in fluorescence intensity of C10DA(0.20×10-5 mol/L) upon the titration of Q[7] in water (A) n(Q[7])/n(C10DA) from a to s: 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, 3.2, 3.4, 3.6; (B) If-n(Q[7])/n(C10DA) curve of Q[7]-C10DA system; λex=256 nm, λem=369 nm.

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