Calix[4]arene-based chromogenic chemosensor for the α-phenylglycine anion: Synthesis and chiral recognition

Guang Yan Qing; Yong Bing He; Yang Zhao; Chen Guang Hu; Shun Ying Liu; Xi Yang

doi:10.1002/ejoc.200500704

Calix[4]arene-based chromogenic chemosensor for the α-phenylglycine anion: Synthesis and chiral recognition

Guang Yan Qing
, Yong Bing He^*
, Yang Zhao
, Chen Guang Hu
, Shun Ying Liu
, Xi Yang

^*此作品的通讯作者

Wuhan University

科研成果: 期刊稿件 › 文章 › 同行评审

66 引用（Scopus）

摘要

Calix[4]arene-based two-armed chiral anion receptors 3a and 3b have been synthesized and examined for their chiral anion-binding abilities by UV/Vis absorption and ¹H NMR spectroscopy. The results of nonlinear curve fitting indicate that 3a and 3b form 1:1 stoichiometric complexes with the L- or D-α-phenylglycine anion by multiple hydrogen-bonding interactions and exhibit good enantioselective recognition for the enantiomers of the α-phenylglycine anions (3a: K_ass(L)/K_ass(D) = 4.76; 3b: K_ass(D)/K_ass(L) = 2.84). The marked colour changes observed for the complexation of 3a with the chiral anions and the good enantioselective recognition reveal that receptor 3a could be used as a good chiral chromogenic chemosensor for the enantiomers of the α-phenylglycine anion.

源语言	英语
页（从-至）	1574-1580
页数	7
期刊	European Journal of Organic Chemistry
期	6
DOI	https://doi.org/10.1002/ejoc.200500704
出版状态	已出版 - 13 3月 2006
已对外发布	是

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@article{a9e87c7ef79748d5b41a2d1ce7713f3d,

title = "Calix[4]arene-based chromogenic chemosensor for the α-phenylglycine anion: Synthesis and chiral recognition",

abstract = "Calix[4]arene-based two-armed chiral anion receptors 3a and 3b have been synthesized and examined for their chiral anion-binding abilities by UV/Vis absorption and 1H NMR spectroscopy. The results of nonlinear curve fitting indicate that 3a and 3b form 1:1 stoichiometric complexes with the L- or D-α-phenylglycine anion by multiple hydrogen-bonding interactions and exhibit good enantioselective recognition for the enantiomers of the α-phenylglycine anions (3a: Kass(L)/Kass(D) = 4.76; 3b: Kass(D)/Kass(L) = 2.84). The marked colour changes observed for the complexation of 3a with the chiral anions and the good enantioselective recognition reveal that receptor 3a could be used as a good chiral chromogenic chemosensor for the enantiomers of the α-phenylglycine anion.",

keywords = "Anion receptor, Calixarenes, Chiral recognition, Chirality, Chromogenic sensor, UV/Vis spectra",

author = "Qing, \{Guang Yan\} and He, \{Yong Bing\} and Yang Zhao and Hu, \{Chen Guang\} and Liu, \{Shun Ying\} and Xi Yang",

year = "2006",

month = mar,

day = "13",

doi = "10.1002/ejoc.200500704",

language = "英语",

pages = "1574--1580",

journal = "European Journal of Organic Chemistry",

issn = "1434-193X",

publisher = "Wiley-VCH Verlag",

number = "6",

}

TY - JOUR

T1 - Calix[4]arene-based chromogenic chemosensor for the α-phenylglycine anion

T2 - Synthesis and chiral recognition

AU - Qing, Guang Yan

AU - He, Yong Bing

AU - Zhao, Yang

AU - Hu, Chen Guang

AU - Liu, Shun Ying

AU - Yang, Xi

PY - 2006/3/13

Y1 - 2006/3/13

N2 - Calix[4]arene-based two-armed chiral anion receptors 3a and 3b have been synthesized and examined for their chiral anion-binding abilities by UV/Vis absorption and 1H NMR spectroscopy. The results of nonlinear curve fitting indicate that 3a and 3b form 1:1 stoichiometric complexes with the L- or D-α-phenylglycine anion by multiple hydrogen-bonding interactions and exhibit good enantioselective recognition for the enantiomers of the α-phenylglycine anions (3a: Kass(L)/Kass(D) = 4.76; 3b: Kass(D)/Kass(L) = 2.84). The marked colour changes observed for the complexation of 3a with the chiral anions and the good enantioselective recognition reveal that receptor 3a could be used as a good chiral chromogenic chemosensor for the enantiomers of the α-phenylglycine anion.

AB - Calix[4]arene-based two-armed chiral anion receptors 3a and 3b have been synthesized and examined for their chiral anion-binding abilities by UV/Vis absorption and 1H NMR spectroscopy. The results of nonlinear curve fitting indicate that 3a and 3b form 1:1 stoichiometric complexes with the L- or D-α-phenylglycine anion by multiple hydrogen-bonding interactions and exhibit good enantioselective recognition for the enantiomers of the α-phenylglycine anions (3a: Kass(L)/Kass(D) = 4.76; 3b: Kass(D)/Kass(L) = 2.84). The marked colour changes observed for the complexation of 3a with the chiral anions and the good enantioselective recognition reveal that receptor 3a could be used as a good chiral chromogenic chemosensor for the enantiomers of the α-phenylglycine anion.

KW - Anion receptor

KW - Calixarenes

KW - Chiral recognition

KW - Chirality

KW - Chromogenic sensor

KW - UV/Vis spectra

UR - https://www.scopus.com/pages/publications/33645053485

U2 - 10.1002/ejoc.200500704

DO - 10.1002/ejoc.200500704

M3 - 文章

AN - SCOPUS:33645053485

SN - 1434-193X

SP - 1574

EP - 1580

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 6

ER -

Calix[4]arene-based chromogenic chemosensor for the α-phenylglycine anion: Synthesis and chiral recognition

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