显色偶氮偶联杯[4]芳烃
Chromogenic azo-coupled calix[4]arenes.
作者信息
Kim Jong Seung, Shon Ok Jae, Lee Jae Kwang, Lee Soo Heon, Kim Jong Yeol, Park Ki-Min, Lee Shim Sung
机构信息
Department of Chemistry, Konyang University, Nonsan 320-711, Korea.
出版信息
J Org Chem. 2002 Feb 22;67(4):1372-5. doi: 10.1021/jo0108921.
Novel 1,3-alternate calix[4]azacrowns having an azo chromophoric pendent group were synthesized, and their 1,3-alternate conformations were confirmed by X-ray crystal structure. In view of the hypsochromical UV band shifting upon cation complexation, azo-coupled calix[4]azacrown-5 (3) showed the most selective shifting with alkali and alkaline metal ions. In addition, 3 revealed K+ ion selectivity not only due to the size comparability between the K+ ion and the azacrown-5 loop but also due to a significant K+-pi interaction between the two aromatic rings and the K+ ion. The UV band shifting is also dependent on the lipophilicity of the species of counteranion used.
合成了带有偶氮发色团侧基的新型1,3-交替杯[4]氮杂冠醚，其1,3-交替构象通过X射线晶体结构得以证实。鉴于阳离子络合时紫外吸收带发生蓝移，偶氮偶联的杯[4]氮杂冠-5（3）对碱金属和碱土金属离子表现出最具选择性的吸收带移动。此外，3表现出对K⁺离子的选择性，这不仅是因为K⁺离子与氮杂冠-5环之间的尺寸匹配，还因为两个芳香环与K⁺离子之间存在显著的K⁺-π相互作用。紫外吸收带的移动还取决于所用抗衡离子种类的亲脂性。
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