Chromogenic azo-coupled calix[4]arenes

Seung Kim Jong, Jae Shon Ok, Kwang Lee Jae, Heon Lee Soo, Yeol Kim Jong, Ki Min Park, Sung Lee Shim

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10 Citations (Scopus)

Abstract

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+-π 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.

Original languageEnglish
Pages (from-to)1372-1375
Number of pages4
JournalJournal of Organic Chemistry
Volume67
Issue number4
DOIs
Publication statusPublished - 2002 Feb 22

ASJC Scopus subject areas

  • Organic Chemistry

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  • Cite this

    Jong, S. K., Ok, J. S., Jae, K. L., Soo, H. L., Jong, Y. K., Park, K. M., & Shim, S. L. (2002). Chromogenic azo-coupled calix[4]arenes. Journal of Organic Chemistry, 67(4), 1372-1375. https://doi.org/10.1021/jo0108921