Cucurbit[7]uril Complexes of Crown-Ether Derived Styryl and (Bis)styryl Dyes
Cucurbit[7]uril Complexes of Crown-Ether Derived Styryl and (Bis)styryl Dyes
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DOI：
10.1021/jp903289q
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发表时间：
2009-07-30
影响因子：
3.3
通讯作者：
Isaacs, Lyle
中科院分区：
文献类型：
--
作者：
Fedorova, Olga A.;Chernikova, Ekaterina Yu.;Isaacs, Lyle
本文报道了CB[7]分子容器与冠醚苯乙烯基和（双）苯乙烯基染料1-6的相互作用。单苯乙烯基染料（1和2）与CB[7]的相互作用导致形成1：1络合物，其中CB[7]分子位于客体的区域上，该区域包括吡啶鎓环、C=C双键和苯并冠醚1和2的一部分芳环。对于（双）苯乙烯基染料（3-5），通过光学和电喷雾离子化质谱（ESI-MS）方法的组合证实了与组合染料CB[7].dye和CB[7].dye.CB[7]形成两种类型的络合物。在（双）苯乙烯基染料（6）的情况下，形成2：1和1：1组合物6.CB[7].6和CB[7].6。配合物的形成伴随着染料的光学特性的实质性变化和长寿命的受激准分子物种的形成。我们测试了该系统对金属离子的刺激反应。我们发现，金属离子更喜欢结合到CB[7]的静电负脲基C=O门户，而不是与苯乙烯基染料的冠醚部分。
In this paper, we report the interaction of the CB[7] molecular container with crown ether styryl and (bis)styryl dyes 1-6. The interaction of monostyryl dyes (1 and 2) with CB[7] results in the formation of 1:1 complexes where the CB[7] molecule is located on the region of the guest encompassing the pyridinium ring, C=C double bond, and a portion of the aryl ring of benzocrown ethers 1 and 2. For (bis)styryl dyes (3-5), the formation of two types of complexes with composition dye.CB[7].dye and CB[7].dye.CB[7] was confirmed by a combination of optical and electrospray ionization mass spectroscopy (ESI-MS) methods. In the case of (bis)styryl dye (6), both 2:1 and 1:1 compositions 6.CB[7].6 and CB[7].6 were formed. Complex formation is accompanied by substantial changes in the optical characteristics of the dyes and formation of long-lived excimer species. We tested the stimuli responsiveness of this system in response to metal ions. We find that the metal ions prefer to bind to the electrostatically negative ureidyl C=O portals of the CB[7] rather than with the crown ether moiety of the styryl dyes.