Thiourea-isothiouronium conjugate for strong and selective binding of very hydrophilic H2PO4- anion at the 1,2-dichloroethane-water interface

Ryo Kato; Ying Yu Cui; Seiichi Nishizawa; Tomoyuki Yokobori; Norio Teramae

doi:10.1016/j.tetlet.2004.04.001

Thiourea-isothiouronium conjugate for strong and selective binding of very hydrophilic H₂PO₄^- anion at the 1,2-dichloroethane-water interface

Ryo Kato, Ying Yu Cui, Seiichi Nishizawa, Tomoyuki Yokobori, Norio Teramae

SCI - Chemistry

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

41 Citations (Scopus)

Abstract

Potential use of a surfactant-like receptor is demonstrated at the 1,2-dichloroethane-water interface for strong and selective binding of H ₂PO₄^- over Br^- and Cl^-. The analysis by interfacial tensiometry reveals that the interfacial adsorption of a thiourea-isothiouronium conjugate, BT-C₁, is significantly stabilized by the binding of H₂PO₄^- with the adsorption constant of 1.7×10⁵M^-1 while the interfacial adsorptivity of this receptor is relatively moderate for Br ^- (0.81×10⁵M^-1) and Cl^- (0.63×10⁵M^-1). Such complexation-induced interfacial adsorption behaviors of BT-C₁ are discussed as a basis for the development of receptor-based chemical sensors for phosphate anions.

Original language	English
Pages (from-to)	4273-4276
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	22
DOIs	https://doi.org/10.1016/j.tetlet.2004.04.001
Publication status	Published - 2004 May 24

Keywords

Adsorption
Anion
Interface
Isothiouronium
Phosphate
Receptor
Recognition
Thiourea

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{83c498df4d394e19a744dabc1fce92c8,

title = "Thiourea-isothiouronium conjugate for strong and selective binding of very hydrophilic H2PO4- anion at the 1,2-dichloroethane-water interface",

abstract = "Potential use of a surfactant-like receptor is demonstrated at the 1,2-dichloroethane-water interface for strong and selective binding of H 2PO4- over Br- and Cl-. The analysis by interfacial tensiometry reveals that the interfacial adsorption of a thiourea-isothiouronium conjugate, BT-C1, is significantly stabilized by the binding of H2PO4- with the adsorption constant of 1.7×105M-1 while the interfacial adsorptivity of this receptor is relatively moderate for Br - (0.81×105M-1) and Cl- (0.63×105M-1). Such complexation-induced interfacial adsorption behaviors of BT-C1 are discussed as a basis for the development of receptor-based chemical sensors for phosphate anions.",

keywords = "Adsorption, Anion, Interface, Isothiouronium, Phosphate, Receptor, Recognition, Thiourea",

author = "Ryo Kato and Cui, {Ying Yu} and Seiichi Nishizawa and Tomoyuki Yokobori and Norio Teramae",

note = "Funding Information: We thank Drs. Hinako Ando and Kazuo Sasaki, Instrumental Analysis Center for Chemistry, Faculty of Science, Tohoku University, for microanalyses and 1 H NMR measurements. This work was partially supported by Grants-in-Aid for Scientific Research (A), No 14204074, for Scientific Research on Priority Research Areas (B), No 13129201, and for the COE Project, Giant Molecules and Complex Systems, 2003, from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. Partial support by RFTF from the Japan Society for Promotion of Science (JSPS) is also acknowledged.",

year = "2004",

month = may,

day = "24",

doi = "10.1016/j.tetlet.2004.04.001",

language = "English",

volume = "45",

pages = "4273--4276",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "22",

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TY - JOUR

T1 - Thiourea-isothiouronium conjugate for strong and selective binding of very hydrophilic H2PO4- anion at the 1,2-dichloroethane-water interface

AU - Kato, Ryo

AU - Cui, Ying Yu

AU - Nishizawa, Seiichi

AU - Yokobori, Tomoyuki

AU - Teramae, Norio

N1 - Funding Information: We thank Drs. Hinako Ando and Kazuo Sasaki, Instrumental Analysis Center for Chemistry, Faculty of Science, Tohoku University, for microanalyses and 1 H NMR measurements. This work was partially supported by Grants-in-Aid for Scientific Research (A), No 14204074, for Scientific Research on Priority Research Areas (B), No 13129201, and for the COE Project, Giant Molecules and Complex Systems, 2003, from the Ministry of Education, Culture, Sports, Science, and Technology, Japan. Partial support by RFTF from the Japan Society for Promotion of Science (JSPS) is also acknowledged.

PY - 2004/5/24

Y1 - 2004/5/24

N2 - Potential use of a surfactant-like receptor is demonstrated at the 1,2-dichloroethane-water interface for strong and selective binding of H 2PO4- over Br- and Cl-. The analysis by interfacial tensiometry reveals that the interfacial adsorption of a thiourea-isothiouronium conjugate, BT-C1, is significantly stabilized by the binding of H2PO4- with the adsorption constant of 1.7×105M-1 while the interfacial adsorptivity of this receptor is relatively moderate for Br - (0.81×105M-1) and Cl- (0.63×105M-1). Such complexation-induced interfacial adsorption behaviors of BT-C1 are discussed as a basis for the development of receptor-based chemical sensors for phosphate anions.

AB - Potential use of a surfactant-like receptor is demonstrated at the 1,2-dichloroethane-water interface for strong and selective binding of H 2PO4- over Br- and Cl-. The analysis by interfacial tensiometry reveals that the interfacial adsorption of a thiourea-isothiouronium conjugate, BT-C1, is significantly stabilized by the binding of H2PO4- with the adsorption constant of 1.7×105M-1 while the interfacial adsorptivity of this receptor is relatively moderate for Br - (0.81×105M-1) and Cl- (0.63×105M-1). Such complexation-induced interfacial adsorption behaviors of BT-C1 are discussed as a basis for the development of receptor-based chemical sensors for phosphate anions.

KW - Adsorption

KW - Anion

KW - Interface

KW - Isothiouronium

KW - Phosphate

KW - Receptor

KW - Recognition

KW - Thiourea

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JO - Tetrahedron Letters

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