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首页> 外文期刊>Bulletin of the Chemical Society of Japan >Syntheses,Structures,and Properties of Quinone-Bridged Calix[6]arenes
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Syntheses,Structures,and Properties of Quinone-Bridged Calix[6]arenes

机译：醌桥杯[6]芳烃的合成，结构与性质

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摘要

The quinone-bridged calix[6]arenes 1 and 2,carrying a 1,4-benzoquinone moiety in the cavity of a calixarene mac-rocycle,were synthesized from the corresponding p-methoxyphenol derivatives.X-ray crystallography revealed the structures of 1 and 2,in which the quinone moiety is located inside the cone-shaped calix[6]arene framework and surrounded by the lower-rim substituents.Their ~1H NMR spectra showed upfield shifts of the protons on the bridging unit in comparison with reference compounds without the calixarene framework,in accordance with their crystal structures.The cyclic voltammograms of 1 and 2 showed two waves,the second ones being considerably broadened.Their reduction potentials were found to be negatively shifted in comparison with those of the reference compounds.These shifts were explained in terms of the nonbonded interaction between the ether oxygen atoms of the calixarene moiety and the quinone moiety,as well as the sterically restricted access of the counter cation to the semiquinone anion radical.Reactions of 1 with hydroxylamine and phenylhydrazine afforded the corresponding hydroquinone along with the quinone monoimine derivatives,indicating that electron transfer from the amines proceeds quickly,although the negatively shifted reduction potentials of 1 are apparently unfavorable for the electron transfer process.
机译：用相应的对甲氧基苯酚衍生物合成了在杯芳烃大环腔中带有1，4-苯醌部分的桥联芳烃[6]芳烃1和2。X射线晶体学揭示了1的结构。和2，其中醌部分位于圆锥形杯[6]芳烃骨架内，并被下缘取代基包围。它们的〜1H NMR光谱显示，与参考化合物相比，桥联单元上质子的高场位移1和2的循环伏安图显示了两个波，第二个波明显变宽了。与参考化合物相比，它们的还原电势有负移。用杯芳烃部分的醚氧原子与醌部分之间的非键相互作用以及对位阳离子对t的空间限制进入进行了解释1与羟胺和苯肼的反应提供了相应的对苯二酚和醌单亚胺衍生物，这表明胺的电子转移迅速进行，尽管1的负移还原电势显然不利于电子转移过程。

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