Specific chiral sensing of amino acids using induced circularly polarized luminescence of bis(diimine)dicarboxylic acid europium(III) complexes

Kazuhiro Okutani; Koichi Nozaki; Munetaka Iwamura

doi:10.1021/ic500196m

Specific chiral sensing of amino acids using induced circularly polarized luminescence of bis(diimine)dicarboxylic acid europium(III) complexes

Kazuhiro Okutani, Koichi Nozaki, Munetaka Iwamura^*

^*Corresponding author for this work

Department of Chemistry

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

73 Scopus citations

Abstract

The circularly polarized luminescence (CPL) from [Eu(pda)₂] ^- (pda = 1,10-phenanthroline-2,9-dicarboxylic acid) and [Eu(bda) ₂]^- (bda = 2,2-bipyridine-6,6-dicarboxylic acid) in aqueous solutions containing various amino acids was investigated. The europium(III) complexes exhibited bright-red luminescence assignable to the f-f transition of the Eu^III ion when irradiated with UV light. Although the luminescence was not circularly polarized in the solid state or in aqueous solutions, in accordance with the achiral crystal structure, the complexes exhibited detectable induced CPL (iCPL) in aqueous solutions containing chiral amino acids. In the presence of l-pyrrolidonecarboxylic acid, both [Eu(pda) ₂]^- and [Eu(bda)₂]^- showed similar iCPL intensity (g_lum ∼ 0.03 for the ⁵D₀ → ⁷F₁ transition at 1 mol·dm^-3 of the amino acid). On the other hand, in the presence of l-histidine or l-arginine, [Eu(pda)₂]^- exhibited intense CPL (g _lum ∼ 0.08 for the ⁵D₀ → ⁷F₁ transition at 0.10 mol·dm^-3 of the amino acid), whereas quite weak CPL was observed for [Eu(bda)₂] ^- under the same conditions (g_lum < 0.01). On the basis of analysis of the iCPL intensities in the presence of 12 amino acids, [Eu(pda)₂]^- was found to be a good chiral CPL probe with high sensitivity (about 10^-2 mol·dm^-3) and high selectivity for l-histidine at pH 3 and for l-arginine at pH 7. The mechanism of iCPL was evaluated by analysis of the fine structures in the luminescence spectra and the amino acid concentration dependence of g_lum. For the [Eu(pda)₂]^--histidine/arginine systems, the europium(III) complexes possess coordination structures similar to that in the crystal with slight distortion to form a chiral structure due to specific interaction with two zwitterionic amino acids. This mechanism was in stark contrast to that of the europium(III) complex-pyrrolidonecarboxylic acid system in which one amino acid coordinates to the Eu^III ion to yield an achiral coordination structure.

Original language	English
Pages (from-to)	5527-5537
Number of pages	11
Journal	Inorganic Chemistry
Volume	53
Issue number	11
DOIs	https://doi.org/10.1021/ic500196m
State	Published - 2014/06/02

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Physical and Theoretical Chemistry
Inorganic Chemistry

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@article{656512c800ee4c21b3c8864fb6cd1ad3,

title = "Specific chiral sensing of amino acids using induced circularly polarized luminescence of bis(diimine)dicarboxylic acid europium(III) complexes",

abstract = "The circularly polarized luminescence (CPL) from [Eu(pda)2] - (pda = 1,10-phenanthroline-2,9-dicarboxylic acid) and [Eu(bda) 2]- (bda = 2,2-bipyridine-6,6-dicarboxylic acid) in aqueous solutions containing various amino acids was investigated. The europium(III) complexes exhibited bright-red luminescence assignable to the f-f transition of the EuIII ion when irradiated with UV light. Although the luminescence was not circularly polarized in the solid state or in aqueous solutions, in accordance with the achiral crystal structure, the complexes exhibited detectable induced CPL (iCPL) in aqueous solutions containing chiral amino acids. In the presence of l-pyrrolidonecarboxylic acid, both [Eu(pda) 2]- and [Eu(bda)2]- showed similar iCPL intensity (glum ∼ 0.03 for the 5D0 → 7F1 transition at 1 mol·dm-3 of the amino acid). On the other hand, in the presence of l-histidine or l-arginine, [Eu(pda)2]- exhibited intense CPL (g lum ∼ 0.08 for the 5D0 → 7F1 transition at 0.10 mol·dm-3 of the amino acid), whereas quite weak CPL was observed for [Eu(bda)2] - under the same conditions (glum < 0.01). On the basis of analysis of the iCPL intensities in the presence of 12 amino acids, [Eu(pda)2]- was found to be a good chiral CPL probe with high sensitivity (about 10-2 mol·dm-3) and high selectivity for l-histidine at pH 3 and for l-arginine at pH 7. The mechanism of iCPL was evaluated by analysis of the fine structures in the luminescence spectra and the amino acid concentration dependence of glum. For the [Eu(pda)2]--histidine/arginine systems, the europium(III) complexes possess coordination structures similar to that in the crystal with slight distortion to form a chiral structure due to specific interaction with two zwitterionic amino acids. This mechanism was in stark contrast to that of the europium(III) complex-pyrrolidonecarboxylic acid system in which one amino acid coordinates to the EuIII ion to yield an achiral coordination structure.",

author = "Kazuhiro Okutani and Koichi Nozaki and Munetaka Iwamura",

year = "2014",

month = jun,

day = "2",

doi = "10.1021/ic500196m",

language = "英語",

volume = "53",

pages = "5527--5537",

journal = "Inorganic Chemistry",

issn = "0020-1669",

publisher = "American Chemical Society",

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TY - JOUR

T1 - Specific chiral sensing of amino acids using induced circularly polarized luminescence of bis(diimine)dicarboxylic acid europium(III) complexes

AU - Okutani, Kazuhiro

AU - Nozaki, Koichi

AU - Iwamura, Munetaka

PY - 2014/6/2

Y1 - 2014/6/2

N2 - The circularly polarized luminescence (CPL) from [Eu(pda)2] - (pda = 1,10-phenanthroline-2,9-dicarboxylic acid) and [Eu(bda) 2]- (bda = 2,2-bipyridine-6,6-dicarboxylic acid) in aqueous solutions containing various amino acids was investigated. The europium(III) complexes exhibited bright-red luminescence assignable to the f-f transition of the EuIII ion when irradiated with UV light. Although the luminescence was not circularly polarized in the solid state or in aqueous solutions, in accordance with the achiral crystal structure, the complexes exhibited detectable induced CPL (iCPL) in aqueous solutions containing chiral amino acids. In the presence of l-pyrrolidonecarboxylic acid, both [Eu(pda) 2]- and [Eu(bda)2]- showed similar iCPL intensity (glum ∼ 0.03 for the 5D0 → 7F1 transition at 1 mol·dm-3 of the amino acid). On the other hand, in the presence of l-histidine or l-arginine, [Eu(pda)2]- exhibited intense CPL (g lum ∼ 0.08 for the 5D0 → 7F1 transition at 0.10 mol·dm-3 of the amino acid), whereas quite weak CPL was observed for [Eu(bda)2] - under the same conditions (glum < 0.01). On the basis of analysis of the iCPL intensities in the presence of 12 amino acids, [Eu(pda)2]- was found to be a good chiral CPL probe with high sensitivity (about 10-2 mol·dm-3) and high selectivity for l-histidine at pH 3 and for l-arginine at pH 7. The mechanism of iCPL was evaluated by analysis of the fine structures in the luminescence spectra and the amino acid concentration dependence of glum. For the [Eu(pda)2]--histidine/arginine systems, the europium(III) complexes possess coordination structures similar to that in the crystal with slight distortion to form a chiral structure due to specific interaction with two zwitterionic amino acids. This mechanism was in stark contrast to that of the europium(III) complex-pyrrolidonecarboxylic acid system in which one amino acid coordinates to the EuIII ion to yield an achiral coordination structure.

AB - The circularly polarized luminescence (CPL) from [Eu(pda)2] - (pda = 1,10-phenanthroline-2,9-dicarboxylic acid) and [Eu(bda) 2]- (bda = 2,2-bipyridine-6,6-dicarboxylic acid) in aqueous solutions containing various amino acids was investigated. The europium(III) complexes exhibited bright-red luminescence assignable to the f-f transition of the EuIII ion when irradiated with UV light. Although the luminescence was not circularly polarized in the solid state or in aqueous solutions, in accordance with the achiral crystal structure, the complexes exhibited detectable induced CPL (iCPL) in aqueous solutions containing chiral amino acids. In the presence of l-pyrrolidonecarboxylic acid, both [Eu(pda) 2]- and [Eu(bda)2]- showed similar iCPL intensity (glum ∼ 0.03 for the 5D0 → 7F1 transition at 1 mol·dm-3 of the amino acid). On the other hand, in the presence of l-histidine or l-arginine, [Eu(pda)2]- exhibited intense CPL (g lum ∼ 0.08 for the 5D0 → 7F1 transition at 0.10 mol·dm-3 of the amino acid), whereas quite weak CPL was observed for [Eu(bda)2] - under the same conditions (glum < 0.01). On the basis of analysis of the iCPL intensities in the presence of 12 amino acids, [Eu(pda)2]- was found to be a good chiral CPL probe with high sensitivity (about 10-2 mol·dm-3) and high selectivity for l-histidine at pH 3 and for l-arginine at pH 7. The mechanism of iCPL was evaluated by analysis of the fine structures in the luminescence spectra and the amino acid concentration dependence of glum. For the [Eu(pda)2]--histidine/arginine systems, the europium(III) complexes possess coordination structures similar to that in the crystal with slight distortion to form a chiral structure due to specific interaction with two zwitterionic amino acids. This mechanism was in stark contrast to that of the europium(III) complex-pyrrolidonecarboxylic acid system in which one amino acid coordinates to the EuIII ion to yield an achiral coordination structure.

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U2 - 10.1021/ic500196m

DO - 10.1021/ic500196m

M3 - 学術論文

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AN - SCOPUS:84901773926

SN - 0020-1669

VL - 53

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JO - Inorganic Chemistry

JF - Inorganic Chemistry

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ER -

Specific chiral sensing of amino acids using induced circularly polarized luminescence of bis(diimine)dicarboxylic acid europium(III) complexes

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