Cooperative molecular recognition of dyes by two bis(尾-cyclodextrin)s with aromatic, sulfur-containing, diamine tethers
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- 作者：Juan Gu (1)
Shao-Ming Chi (1)
Ming-Hua Liu (1)
Rong Huang (2)
Yong Zhao (1)
Bang-Jing Wang (1)
Yan Zhao (1) zhaooyann@163.com - 关键词：Bridged bis(β ; CD)s – ; Dyes – ; Cooperative binding – ; Inclusion phenomena – ; Molecular recognition
- 刊名：Research on Chemical Intermediates
- 出版时间：January 2011
- 出版年：2011
- 期刊代码：37_1568-5675
- 类别：ch
- 卷：37
- 期：1
- 页码：19-30
- 数据来源：sp
摘要
The molecular binding behavior of two bis(β-cyclodextrin (CD))s, that is, 4,4′-diaminodiphenylsulfone-bridged bis(β-CD) 2 and 4,4′-diaminodiphenyldisulfide-bridged bis(β-CD) 3 with some representative organic dyes, i.e., acridine red (AR), neutral red (NR), ammonium 8-anilino-1-naphthalenesulfonate (ANS), sodium 2-(p-toluidinyl)naphthalenesulfonate (TNS), rhodamine B (RhB), and brilliant green (BG), has been investigated at 25 掳C in phosphate buffer (pH 7.20) by ultraviolet, fluorescence and 2D NMR spectroscopy. The fluorescence of ANS, TNS, AR, and NR are enhanced, whereas that of RhB is quenched, by inclusion complexation with both host compounds. The results obtained show bridged bis(β-CD)s 2 and 3 with dye guests give higher complex stability constants (K S) than those of the native β-CD 1, through cooperative binding of two hydrophobic CD cavities with one guest. In addition, the K S values of all guests with host 3 are much larger than those with 2 except for NR as guest. The 2D 1H NOESY spectrum of host 3 and RhB was acquired to confirm the cooperative binding mode. The molecular binding ability of dyes by hosts 1–3 are discussed from the viewpoint of the size and shape-fitting relationship between host and guest.