Novel calix[4]arene-based receptors with bis-squaramide moieties for colorimetric sensing of anions via two different interaction modes

Can Jin; Man Zhang; Chao Deng; Yangfan Guan; Jun Gong; Dunru Zhu; Yi Pan; Juli Jiang; Leyong Wang

doi:10.1016/j.tetlet.2012.11.117

Novel calix[4]arene-based receptors with bis-squaramide moieties for colorimetric sensing of anions via two different interaction modes

Can Jin, Man Zhang, Chao Deng, Yangfan Guan, Jun Gong, Dunru Zhu, Yi Pan, Juli Jiang, Leyong Wang

College of Chemical Engineering

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

50 Scopus citations

Abstract

Novel calix[4]arene-based anion receptors 1-3 with bis-squaramide moieties were designed and synthesized. Their sensing properties with various anions were investigated by UV-vis, ESI-MS, and ¹H NMR spectra. The experimental results revealed that there were two types of interaction modes where receptor 1 bound biologically important H₂PO₄^-, F ^-, and AcO^- ions selectively over other anions in the hydrogen bonding interaction mode, while receptors 2 and 3 displayed deprotonation behavior with basic anions (F^-, AcO^-, and H₂PO₄^-) via acid-base interaction mode. Receptors 2 and 3 were proved to be efficient 'naked-eye' sensors for F ^- and AcO^- with marked color changes.

Original language	English
Pages (from-to)	796-801
Number of pages	6
Journal	Tetrahedron Letters
Volume	54
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2012.11.117
State	Published - 20 Feb 2013

Keywords

Anion receptor
Anion recognition
Calix[4]arene
Interaction mode
Squaramide

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10.1016/j.tetlet.2012.11.117

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title = "Novel calix[4]arene-based receptors with bis-squaramide moieties for colorimetric sensing of anions via two different interaction modes",

abstract = "Novel calix[4]arene-based anion receptors 1-3 with bis-squaramide moieties were designed and synthesized. Their sensing properties with various anions were investigated by UV-vis, ESI-MS, and 1H NMR spectra. The experimental results revealed that there were two types of interaction modes where receptor 1 bound biologically important H2PO4-, F -, and AcO- ions selectively over other anions in the hydrogen bonding interaction mode, while receptors 2 and 3 displayed deprotonation behavior with basic anions (F-, AcO-, and H2PO4-) via acid-base interaction mode. Receptors 2 and 3 were proved to be efficient 'naked-eye' sensors for F - and AcO- with marked color changes.",

keywords = "Anion receptor, Anion recognition, Calix[4]arene, Interaction mode, Squaramide",

author = "Can Jin and Man Zhang and Chao Deng and Yangfan Guan and Jun Gong and Dunru Zhu and Yi Pan and Juli Jiang and Leyong Wang",

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doi = "10.1016/j.tetlet.2012.11.117",

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T1 - Novel calix[4]arene-based receptors with bis-squaramide moieties for colorimetric sensing of anions via two different interaction modes

AU - Jin, Can

AU - Zhang, Man

AU - Deng, Chao

AU - Guan, Yangfan

AU - Gong, Jun

AU - Zhu, Dunru

AU - Pan, Yi

AU - Jiang, Juli

AU - Wang, Leyong

PY - 2013/2/20

Y1 - 2013/2/20

N2 - Novel calix[4]arene-based anion receptors 1-3 with bis-squaramide moieties were designed and synthesized. Their sensing properties with various anions were investigated by UV-vis, ESI-MS, and 1H NMR spectra. The experimental results revealed that there were two types of interaction modes where receptor 1 bound biologically important H2PO4-, F -, and AcO- ions selectively over other anions in the hydrogen bonding interaction mode, while receptors 2 and 3 displayed deprotonation behavior with basic anions (F-, AcO-, and H2PO4-) via acid-base interaction mode. Receptors 2 and 3 were proved to be efficient 'naked-eye' sensors for F - and AcO- with marked color changes.

AB - Novel calix[4]arene-based anion receptors 1-3 with bis-squaramide moieties were designed and synthesized. Their sensing properties with various anions were investigated by UV-vis, ESI-MS, and 1H NMR spectra. The experimental results revealed that there were two types of interaction modes where receptor 1 bound biologically important H2PO4-, F -, and AcO- ions selectively over other anions in the hydrogen bonding interaction mode, while receptors 2 and 3 displayed deprotonation behavior with basic anions (F-, AcO-, and H2PO4-) via acid-base interaction mode. Receptors 2 and 3 were proved to be efficient 'naked-eye' sensors for F - and AcO- with marked color changes.

KW - Anion receptor

KW - Anion recognition

KW - Calix[4]arene

KW - Interaction mode

KW - Squaramide

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Novel calix[4]arene-based receptors with bis-squaramide moieties for colorimetric sensing of anions via two different interaction modes

Abstract

Keywords

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