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

doi:10.1021/jo0108921

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

Research output: Contribution to journal › Article › peer-review

11 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 language	English
Pages (from-to)	1372-1375
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	67
Issue number	4
DOIs	https://doi.org/10.1021/jo0108921
Publication status	Published - 2002 Feb 22
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo0108921

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title = "Chromogenic azo-coupled calix[4]arenes",

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.",

author = "Jong, {Seung Kim} and Ok, {Jae Shon} and Jae, {Kwang Lee} and Soo, {Heon Lee} and Jong, {Yeol Kim} and Park, {Ki Min} and Shim, {Sung Lee}",

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T1 - Chromogenic azo-coupled calix[4]arenes

AU - Jong, Seung Kim

AU - Ok, Jae Shon

AU - Jae, Kwang Lee

AU - Soo, Heon Lee

AU - Jong, Yeol Kim

AU - Park, Ki Min

AU - Shim, Sung Lee

PY - 2002/2/22

Y1 - 2002/2/22

N2 - 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.

AB - 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.

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Chromogenic azo-coupled calix[4]arenes

Abstract

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