Design and synthesis of preorganized tripodal fluororeceptors based on hydrogen bonding of thiourea groups for optical phosphate ion sensing

S. I. Sasaki, Daniel Citterio, S. Ozawa, K. Suzuki

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109 Citations (Scopus)

Abstract

Expecting a preorganization effect, tripodal anion host molecules were designed and synthesized. It was demonstrated that two kinds of new thiourea derivatives having a six-fold substituted benzene ring as a preorganized spacer were effective for recognition of the tetrahedral dihydrogen phosphate anion. A tripodal fluororeceptor 1 having a pyrene moiety adjacent to the thiourea binding site showed long-wavelength emission upon addition of guest anions in acetonitrile. On the other hand, a tripodal thiourea receptor 2 connected to anthracene groups via methylene units showed a decrease in fluorescence intensity upon addition of anions. In both cases, the degree of the change in emission intensity was in the order of H2PO4 - > CH3COO- > Cl- ≫ ClO4 -, which is clearly different from that of reference compounds having only one binding site. Association constants (Ka) of these tripodal fluororeceptors also confirmed the dihydrogen phosphate selectivity over the more basic acetate anion in this homogeneous solution system. The characteristics of the fluororeceptors using the preorganization effect were shown to be promising for the development of chemical ion sensors with a specific anion selectivity.

Original languageEnglish
Pages (from-to)2309-2313
Number of pages5
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number12
Publication statusPublished - 2001

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Thiourea
Anions
Hydrogen bonds
Phosphates
Ions
Binding Sites
Benzene
Acetates
Fluorescence
Derivatives
Wavelength
Molecules
Sensors

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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title = "Design and synthesis of preorganized tripodal fluororeceptors based on hydrogen bonding of thiourea groups for optical phosphate ion sensing",
abstract = "Expecting a preorganization effect, tripodal anion host molecules were designed and synthesized. It was demonstrated that two kinds of new thiourea derivatives having a six-fold substituted benzene ring as a preorganized spacer were effective for recognition of the tetrahedral dihydrogen phosphate anion. A tripodal fluororeceptor 1 having a pyrene moiety adjacent to the thiourea binding site showed long-wavelength emission upon addition of guest anions in acetonitrile. On the other hand, a tripodal thiourea receptor 2 connected to anthracene groups via methylene units showed a decrease in fluorescence intensity upon addition of anions. In both cases, the degree of the change in emission intensity was in the order of H2PO4 - > CH3COO- > Cl- ≫ ClO4 -, which is clearly different from that of reference compounds having only one binding site. Association constants (Ka) of these tripodal fluororeceptors also confirmed the dihydrogen phosphate selectivity over the more basic acetate anion in this homogeneous solution system. The characteristics of the fluororeceptors using the preorganization effect were shown to be promising for the development of chemical ion sensors with a specific anion selectivity.",
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T1 - Design and synthesis of preorganized tripodal fluororeceptors based on hydrogen bonding of thiourea groups for optical phosphate ion sensing

AU - Sasaki, S. I.

AU - Citterio, Daniel

AU - Ozawa, S.

AU - Suzuki, K.

PY - 2001

Y1 - 2001

N2 - Expecting a preorganization effect, tripodal anion host molecules were designed and synthesized. It was demonstrated that two kinds of new thiourea derivatives having a six-fold substituted benzene ring as a preorganized spacer were effective for recognition of the tetrahedral dihydrogen phosphate anion. A tripodal fluororeceptor 1 having a pyrene moiety adjacent to the thiourea binding site showed long-wavelength emission upon addition of guest anions in acetonitrile. On the other hand, a tripodal thiourea receptor 2 connected to anthracene groups via methylene units showed a decrease in fluorescence intensity upon addition of anions. In both cases, the degree of the change in emission intensity was in the order of H2PO4 - > CH3COO- > Cl- ≫ ClO4 -, which is clearly different from that of reference compounds having only one binding site. Association constants (Ka) of these tripodal fluororeceptors also confirmed the dihydrogen phosphate selectivity over the more basic acetate anion in this homogeneous solution system. The characteristics of the fluororeceptors using the preorganization effect were shown to be promising for the development of chemical ion sensors with a specific anion selectivity.

AB - Expecting a preorganization effect, tripodal anion host molecules were designed and synthesized. It was demonstrated that two kinds of new thiourea derivatives having a six-fold substituted benzene ring as a preorganized spacer were effective for recognition of the tetrahedral dihydrogen phosphate anion. A tripodal fluororeceptor 1 having a pyrene moiety adjacent to the thiourea binding site showed long-wavelength emission upon addition of guest anions in acetonitrile. On the other hand, a tripodal thiourea receptor 2 connected to anthracene groups via methylene units showed a decrease in fluorescence intensity upon addition of anions. In both cases, the degree of the change in emission intensity was in the order of H2PO4 - > CH3COO- > Cl- ≫ ClO4 -, which is clearly different from that of reference compounds having only one binding site. Association constants (Ka) of these tripodal fluororeceptors also confirmed the dihydrogen phosphate selectivity over the more basic acetate anion in this homogeneous solution system. The characteristics of the fluororeceptors using the preorganization effect were shown to be promising for the development of chemical ion sensors with a specific anion selectivity.

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