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基于三并苯的大环主体与(9-蒽甲基)苄基铵盐的络合作用:一种 Ba2+ 选择性荧光探针。

Complexation of triptycene-based macrotricyclic host toward (9-anthracylmethyl)benzylammonium salt: a Ba2+ selective fluorescence probe.

机构信息

Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

出版信息

J Org Chem. 2010 Aug 6;75(15):5092-8. doi: 10.1021/jo1008355.

DOI:10.1021/jo1008355
PMID:20597516
Abstract

A new triptycene-based macrotricyclic host containing two dibenzo-30 crown-10 moieties (1) has been synthesized. It could form a 1:2 stable complex 1 x 3(2) with (9-anthracylmethyl)benzylammonium salt (3) in both solution and solid state, in which the 9-anthracyl groups were selectively positioned inside the cavity of the host. Moreover, the complexation and disassociation of complex 1 x 3(2) could be chemically controlled by the addition of base and acid. It was also found that Ba(2+) ion could considerably induce the fluorescence enhancement of complex 1 x 3(2), which might thus be utilized as a selective supramolecular fluorescence probe for Ba(2+) ion. Fluorescence and (1)H NMR spectroscopic titrations further showed that the complexation between complex 1 x 3(2) and barium ions underwent a two-step process.

摘要

一种新型的基于三并苯的大环主体化合物,其中包含两个二苯并-30-冠-10 部分(1),已经被合成出来。它可以在溶液和固态中与(9-蒽甲基)苄基铵盐(3)形成 1:2 的稳定配合物 1 x 3(2),其中 9-蒽基团被选择性地定位在主体的空腔内。此外,通过添加碱和酸可以实现配合物 1 x 3(2)的络合和解离的化学控制。还发现 Ba(2+)离子可以显著诱导配合物 1 x 3(2)的荧光增强,因此可以将其用作 Ba(2+)离子的选择性超分子荧光探针。荧光和(1)H NMR 光谱滴定进一步表明,配合物 1 x 3(2)与钡离子之间的络合经历了一个两步过程。

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