Azathia crown ethers carrying pyrene pendant as receptor molecules for metal sensor systems

Ocak, Ümmühan; Ocak, Miraç; Parlayan, Semanur; Başoğlu, Aysel; Çağlar, Yasemin; Bahadır, Zekeriyya

doi:10.1016/j.jlumin.2010.12.008

Cited by 9 publications

(7 citation statements)

References 34 publications

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“…Several host molecules possessing the modular structure referred above, among them crown ethers too, have been synthesized, and their selectivities for different metal ions or organic cations have been studied [27][28][29][30][31][32][33][34][35][36][37]. Some reported aza-and azathiacrown ethers contain a pyrene fluorophore unit attached by a methylene spacer to the nitrogen atom of the crown ether, which enables PET type fluorescence response in the presence of inorganic cations [38][39][40][41][42]. Optically active azacrown etherbased PET chemosensors having a modular structure and a binaphthyl chiral unit [43] or alkyl groups at their chiral centers [44] were also synthesized.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Complexation Studies of Optically Active Aza- and Diazacrown Ethers Containing a Pyrene Fluorophore Unit

Pál

Gede

Móczár

et al. 2019

Period. Polytech. Chem. Eng.

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Novel enantiopure azacrown [(R,R)-1 and (S,S)-1] and diazacrown [(R,R)-2–(R,R)-4 and (S,S)-2–(S,S)-4] ethers containing a pyrene fluorophore unit and two phenyl groups at their chiral centers were obtained in multistep syntheses. The action of these chemosensors is based on the photoinduced electron transfer (PET) process, thus they show fluorescence enhancement in the presence of protonated primary amines and amino acid esters. Their recognition abilities toward the enantiomers of 1-phenylethylamine hydrogen perchlorate (PEA), 1-(1-naphthyl) ethylamine hydrogen perchlorate (NEA), phenylglycine methyl ester hydrogen perchlorate (PGME), and phenylalanine methyl ester hydrogen perchlorate (PAME) were examined in acetonitrile using fluorescence spectroscopy.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Complexation Studies of Optically Active Aza- and Diazacrown Ethers Containing a Pyrene Fluorophore Unit

Pál

Gede

Móczár

et al. 2019

Period. Polytech. Chem. Eng.

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“…Pyrene and its derivatives are often used as fluorescent materials owing to several advantageous features including photochemical inertness, dual fluorescence (monomer/excimer) and high emission quantum yield . Thus far, many substances containing linked pyrenes and crown ethers have been designed to serve as fluorescent metal ion sensors . These types of sensors can be roughly categorized into three groups based on their response to metal ions.…”

Section: Introductionmentioning

confidence: 99%

“…These types of sensors can be roughly categorized into three groups based on their response to metal ions. The first two sensor groups are those that undergo turn‐ON or turn‐OFF responses typically caused by the removal or installation of photoinduced electron transfer (PET) or heavy atom effect promoted quenching pathways. In the third group, sensing is based on monomer/excimer emission switching induced by changes in spatial distances between two pyrene moieties.…”

Section: Introductionmentioning

confidence: 99%

“…In the third group, sensing is based on monomer/excimer emission switching induced by changes in spatial distances between two pyrene moieties. Moreover, the pyrene and crown ether groups in these types of sensors are normally linked by flexible chains, such as methylene (), ether , oligoethylene glycol , ester , amine , amide (), imine , triazole , sulfoxide and DNA units. As a consequence, decreases in fluorescence efficiencies by thermal (nonradiative) decay pathways arising from molecular motion are inevitable.…”

Section: Introductionmentioning

confidence: 99%

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Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions

Maeda

Tanaka

Aratani

et al. 2019

Photochem & Photobiology

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Substances containing ethynylpyrenes linked to either one or four benzocrown ethers were synthesized, and their absorption and fluorescence spectroscopic responses to metal ions were assessed. Addition of metal perchlorates to solutions of these substances promotes short wavelength shifts in their absorption and fluorescence maxima and increases in their fluorescence intensities. The magnitudes of the fluorescence intensity increases are dependent on the ring size and number of the crown ether and the nature of the metal cation. Association constants for complex formation were calculated using fluorescence intensity versus concentration data. Analysis using Job's plots showed that the substances containing one benzocrown ether moiety form 1:1 complexes with metal ions. Results of experiments employing repeated addition and removal of Mg(ClO4)2 demonstrate that the ON‐OFF fluorescence response can be repeated at least three times. Results of molecular orbital calculations show that complexation with metal ions lowers the energies of both the π and π* levels of the ethynylpyrene moiety and that in some cases the vacant orbital on the metal becomes the LUMO of the complex. An explanation of the spectroscopic changes promoted by metal ions is proposed in terms of electrostatic repulsion and structural regulation.

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“…However, PAN and many macrocycles are often almost insoluble in water [18,19], divorcing them from immediate application in an aqueous medium, a severe limitation for biology or the natural environment where water is the primary solvent. For characterisation, chromoionophoric macrocycles may be dissolved and tested in polar aprotic solvents like acetonitrile, dichloromethane [20] or dimethyl sulfoxide [21] which co-dissolve some metal salts (e.g. picrates).…”

Section: Introductionmentioning

confidence: 99%

Fibre optic absorbance meter with low limit of detection for waterborne cations

Tuwei

Williams

Grell

2016

Sensors and Actuators B: Chemical

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We report an evanescent wave based fibre optic absorbance meter that enables the colorimetric detection of waterborne cations with water insoluble chromoionophoric sensitisers. This establishes an alternative to the PVC membrane based transducers that are conventionally used for this purpose. Here, a water insoluble sensitiser is coated as a thin film on an unclad section of a multimode optical fibre to overlap with the evanescent field of a light beam propagating along the fibre core. The colorimetric response of the sensitiser when in contact with waterborne cation leads to increased absorption of virtual photons associated with the evanescent field. The resulting intensity loss of the propagating beam is detected by a bespoke newly designed self-referenced evanescent wave absorbance meter with beam intensity modulation and Lock-in amplification. We validate our transducer with the well characterised water insoluble sensitizer, 1-(2-pyridylazo)-2-naphthol (PAN), for the detection of aqueous Zn 2+ cations. We find a limit of detection (LoD) of 54 nM Zn 2+ , 28 times lower compared to a PVC membrane based sensor using same sensitiser for same cation (Albero et al., Journal of Pharmaceutical and Biomedical Analysis 29 (2002), 779). Our evanescent wave absorbance meter can easily be adapted to other colorimetric sensitisers, including chromoionophoric complex forming macrocycles.

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Azathia crown ethers carrying pyrene pendant as receptor molecules for metal sensor systems

Cited by 9 publications

References 34 publications

Synthesis and Complexation Studies of Optically Active Aza- and Diazacrown Ethers Containing a Pyrene Fluorophore Unit

Synthesis and Complexation Studies of Optically Active Aza- and Diazacrown Ethers Containing a Pyrene Fluorophore Unit

Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions

Fibre optic absorbance meter with low limit of detection for waterborne cations

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