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

Wuhan University

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

65 Scopus citations

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: 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.

Original language	English
Pages (from-to)	1574-1580
Number of pages	7
Journal	European Journal of Organic Chemistry
Issue number	6
DOIs	https://doi.org/10.1002/ejoc.200500704
State	Published - 13 Mar 2006
Externally published	Yes

Keywords

Anion receptor
Calixarenes
Chiral recognition
Chirality
Chromogenic sensor
UV/Vis spectra

Access to Document

10.1002/ejoc.200500704

Cite this

@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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this