Chromogenic indoaniline armed-calix[4]azacrowns

Jong Seung Kim; Ok Jae Shon; Seung Hwan Yang; Jong Yeol Kim; Moon Jib Kim

doi:10.1021/jo0201169

Chromogenic indoaniline armed-calix[4]azacrowns

Jong Seung Kim, Ok Jae Shon, Seung Hwan Yang, Jong Yeol Kim, Moon Jib Kim

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

42 Citations (Scopus)

Abstract

Two novel chromogenic 1,3-alternate calix[4]azacrown (1) and calix[4]-bis-azacrown (2) in which an indoaniline chromophore was attached on the nitrogen atom of the azacrown unit with one methylene spacer were synthesized. The ¹H NMR spectrum of the ligand 1 and Ca²⁺ proved that the metal ion is entrapped by the calix[4]azacrown unit and by the conjugated indoaniline system. From the UV/vis band shifts upon metal ion complexation, Zn²⁺ ion was found to give the largest band shifts compared to other metal cations, indicating that Zn²⁺ ion (K_a = 18 760 M^-1 for 1 and K_a = 19 930 M^-1 for 2) was selectively encapsulated by the calix[4]azacrown cavity with assistance of the pendent indoaniline sidearm.

Original language	English
Pages (from-to)	6514-6518
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	67
Issue number	18
DOIs	https://doi.org/10.1021/jo0201169
Publication status	Published - 2002 Sept 6
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Chromogenic indoaniline armed-calix[4]azacrowns",

abstract = "Two novel chromogenic 1,3-alternate calix[4]azacrown (1) and calix[4]-bis-azacrown (2) in which an indoaniline chromophore was attached on the nitrogen atom of the azacrown unit with one methylene spacer were synthesized. The 1H NMR spectrum of the ligand 1 and Ca2+ proved that the metal ion is entrapped by the calix[4]azacrown unit and by the conjugated indoaniline system. From the UV/vis band shifts upon metal ion complexation, Zn2+ ion was found to give the largest band shifts compared to other metal cations, indicating that Zn2+ ion (Ka = 18 760 M-1 for 1 and Ka = 19 930 M-1 for 2) was selectively encapsulated by the calix[4]azacrown cavity with assistance of the pendent indoaniline sidearm.",

author = "Kim, {Jong Seung} and Shon, {Ok Jae} and Yang, {Seung Hwan} and Kim, {Jong Yeol} and Kim, {Moon Jib}",

year = "2002",

month = sep,

day = "6",

doi = "10.1021/jo0201169",

language = "English",

volume = "67",

pages = "6514--6518",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Chromogenic indoaniline armed-calix[4]azacrowns

AU - Kim, Jong Seung

AU - Shon, Ok Jae

AU - Yang, Seung Hwan

AU - Kim, Jong Yeol

AU - Kim, Moon Jib

PY - 2002/9/6

Y1 - 2002/9/6

N2 - Two novel chromogenic 1,3-alternate calix[4]azacrown (1) and calix[4]-bis-azacrown (2) in which an indoaniline chromophore was attached on the nitrogen atom of the azacrown unit with one methylene spacer were synthesized. The 1H NMR spectrum of the ligand 1 and Ca2+ proved that the metal ion is entrapped by the calix[4]azacrown unit and by the conjugated indoaniline system. From the UV/vis band shifts upon metal ion complexation, Zn2+ ion was found to give the largest band shifts compared to other metal cations, indicating that Zn2+ ion (Ka = 18 760 M-1 for 1 and Ka = 19 930 M-1 for 2) was selectively encapsulated by the calix[4]azacrown cavity with assistance of the pendent indoaniline sidearm.

AB - Two novel chromogenic 1,3-alternate calix[4]azacrown (1) and calix[4]-bis-azacrown (2) in which an indoaniline chromophore was attached on the nitrogen atom of the azacrown unit with one methylene spacer were synthesized. The 1H NMR spectrum of the ligand 1 and Ca2+ proved that the metal ion is entrapped by the calix[4]azacrown unit and by the conjugated indoaniline system. From the UV/vis band shifts upon metal ion complexation, Zn2+ ion was found to give the largest band shifts compared to other metal cations, indicating that Zn2+ ion (Ka = 18 760 M-1 for 1 and Ka = 19 930 M-1 for 2) was selectively encapsulated by the calix[4]azacrown cavity with assistance of the pendent indoaniline sidearm.

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EP - 6518

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

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ER -

Chromogenic indoaniline armed-calix[4]azacrowns

Abstract

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