Ion-responsive fluorescent compounds. 1. Effect of cation binding on photophysical properties of benzoxazinone derivative linked to monoaza-15-crown-5

Fery–Forgues, Suzanne; Bris, M.-T. Le; Guette, J.‐P.; Valeur, Bernard

doi:10.1021/j100333a013

Cited by 272 publications

(125 citation statements)

References 0 publications

Supporting

Mentioning

112

Contrasting

Unclassified

Order By: Relevance

“…For alkali metal and alkaline earth cations several examples of this strategy are reported for crown ether (2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12), cryptand (13,14), hemispherand (15), calixarene (16,17), and cyclophane hosts (18). Phenols ( l , 4 , 12), polycyclic aromatic (3,13,18), and heteroaromatic chromophores (5,8,9,11) have all been exploited. Despite the successes, there is still a need for photoionophores for alkali metal cations that could be used in aqueous solution over a range of pH values (10).…”

Section: Thomas M F~e Smentioning

confidence: 99%

Photoionophores derived from crown ether polycarboxylic acids: synthesis, ion binding, and spectroscopic characterization

Fyles¹,

Suresh²

1994

Can. J. Chem.

View full text Add to dashboard Cite

Three types of potential photoionophores based on polycarboxylic acid crown ethers were prepared, and their cation complexation behaviours and spectroscopic properties were surveyed. The first type were neutral macropolycyclic hosts prepared by capping across the faces of the crown ether with aromatic diamine chromophores. The second were bis-crown ether carboxylates bearing a bridging aromatic chromophore. The third type appended an additional chromophore-donor site on the crown ether carboxylic acid framework. Cation complexation was examined by potentiometric titration. The neutral ligands were rather poor hosts for alkali metal cations. The other two types of crown ether carboxylates showed a combination of size selectivity and electrostatic stabilization, leading to significant and selective ion binding in water. Ligands of the third type also exhibited cation-dependent absorption spectra in neutral and basic aqueous solution. No significant alkali metal or alkaline earth cation-induced perturbation of the emission spectra was uncovered, but a sodium-and cesium-dependent long wavelength emission enhancement was observed in one of the neutral ligand systems. Photoionophores are selective complexing agents for specific phores investigated. Each case builds on the tendency of the ionic species in which the complexed guest species induces a carboxylic acid groups to occupy axial positions on the macroperturbation in the electronic state of the host molecule. Perturcyclic periphery (22). In case of type A this would lead to capbations can be detected by absorption or emission spectroscopy ping across the face of the macrocycle; hence, this type is to define chromoionophores (1, 2) or fluoroionophores (2), respectively. In principle, ion-selective complexing agents could be modified by addition of a suitable chromophore to yield a functional photoionophore with the selectivity of the unmodified ion-binding host. For alkali metal and alkaline earth cations several examples of this strategy are reported for crown ether (2-12), cryptand (13,14), hemispherand (15), calixarene (16,17), and cyclophane hosts (18). Phenols ( l , 4 , 12), polycyclic aromatic (3, 13, 18), and heteroaromatic chromophores (5, 8,9, 11) have all been exploited. Despite the successes, there is still a need for photoionophores for alkali metal cations that could be used in aqueous solution over a range of pH values (10). The majority of the known photoionophores are either insoluble in water, insensitive to alkali metal cations, or pH sensitive.This paper evaluates several potential photoionophores referred to as captand. The additional arms above and below the macrocyclic plane place the chromophore in proximity to a bound cation and define a three-dimensional cavity (23, 24).Type B is akin to other bis-crown ethers (25), with the additional feature that the chromophore lies between the rings. The crown ethers are expected to act as independent carboxylate crown ethers. Type C unites several themes in crown ether chemistry: lariat ether structu...

show abstract

Section: Thomas M F~e Smentioning

confidence: 99%

Photoionophores derived from crown ether polycarboxylic acids: synthesis, ion binding, and spectroscopic characterization

Fyles¹,

Suresh²

1994

Can. J. Chem.

View full text Add to dashboard Cite

show abstract

“…Another reason could be a side complexation reaction where the metal ion is stabilized by the crown ether but the structure does not undergo a backbone twist. [ 21,22 ] To get a better understanding of the side complexation reaction, a detailed NMR spectroscopy study was carried out with (17-Crown-5)T2 and (20-Crown-6)T2 and different alkali metal salts MX. The structure of the small molecule (17-Crown-5)T2 is shown in Figure 2 a where the crown ether protons (A-D) as well as the aromatic protons (E) are labeled.…”

Section: Characterization Of the Backbone Twistmentioning

confidence: 99%

Sodium and Potassium Ion Selective Conjugated Polymers for Optical Ion Detection in Solution and Solid State

Giovannitti

Nielsen

Rivnay

et al. 2015

Adv Funct Materials

View full text Add to dashboard Cite

This paper presents the development of alkali metal ion selective small molecules and conjugated polymers for optical ion sensing. A crown ether bithiophene unit is chosen as the detecting unit, as both a small molecule and incorporated into a conjugated aromatic structure. The complex formation and the resulting backbone twist of the detector unit is investigated by UV-vis and NMR spectroscopy where a remarkable selectivity toward sodium or potassium ions is found. X-ray diffraction analysis of single crystals with and without alkali metal ions is carried out and a difference of the dihedral angle of more than 70° is observed. In a conjugated polymer structure, the detector unit has a higher sensitivity for alkali metal ion detection than its small molecule analog. Ion selectivity is retained in polymers with solubility in polar solvents facilitated by the attachment of polar ethylene glycol side chains. This design concept is further evolved to develop a sodium-salt solid state sensor based on blends of the detecting polymer with a polyvinyl alcohol matrix where the detection of sodium ions is achieved in aqueous salt solutions with concentrations similar to biologically important environments.

show abstract

“…The emission from the Ir Ⅲ moiety was continuously weakened with the addition of Nd(TTA) 3 -⋅2H 2 O, and when the Nd Ⅲ /Ir Ⅲ ratio of concentration [27] , using the linear approximation method [28] , the relevant expression can be used to illustrate the change in luminescence as follows [29] :…”

Section: Spectrofluorometric Titrationsmentioning

confidence: 99%

Synthesis and photophysical properties of IrIII-LnIII (Ln = Nd, Yb, Er) bimetallic complexes containing bipyrimidines as bridging ligands

Chen

Jiang

Lou

et al. 2009

Sci. China Ser. B-Chem.

View full text Add to dashboard Cite

Bipyrimidines have been chosen as (N^N)(N^N) bridging ligands for connecting metal centers.Ir Ⅲ -Ln Ⅲ(Ln = Nd, Yb, Er) bimetallic complexes [Ir(dfppy) 2 (μ-bpm)Ln(TTA) 3 ]Cl were synthesized by using Ir(dfppy) 2 (bpm)Cl as the ligand coordinating to lanthanide complexes Ln(TTA) 3 ⋅2H 2 O. The stability constants between Ir(dfppy) 2 (bpm)Cl and lanthanide ions were measured by fluorescence titration. The obvious quenching of visible emission from Ir Ⅲ complex in the Ir Ⅲ -Ln Ⅲ (Ln = Nd, Yb, Er) bimetallic complexes indicates that energy transfer occurred from Ir Ⅲ center to lanthanides. NIR emissions from Nd Ⅲ , Yb Ⅲ, and Er Ⅲwere obtained under the excitation of visible light by selective excitation of the Ir Ⅲ -based chromophore. It was proven that Ir(dfppy) 2 (bpm)Cl as the ligand could effectively sensitize NIR emission from Nd Ⅲ , Yb Ⅲ, and Er Ⅲ .

show abstract

Ion-responsive fluorescent compounds. 1. Effect of cation binding on photophysical properties of benzoxazinone derivative linked to monoaza-15-crown-5

Cited by 272 publications

References 0 publications

Photoionophores derived from crown ether polycarboxylic acids: synthesis, ion binding, and spectroscopic characterization

Photoionophores derived from crown ether polycarboxylic acids: synthesis, ion binding, and spectroscopic characterization

Sodium and Potassium Ion Selective Conjugated Polymers for Optical Ion Detection in Solution and Solid State

Synthesis and photophysical properties of IrIII-LnIII (Ln = Nd, Yb, Er) bimetallic complexes containing bipyrimidines as bridging ligands

Contact Info

Product

Resources

About