Synthesis of pyrenocrown ethers as fluorescent sensors and their recognition ability of metal ions

Maeda, Hideaki; Hirose, Kenji; Segi, Masahito

doi:10.1016/j.jlumin.2018.08.032

Cited by 9 publications

(4 citation statements)

References 67 publications

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“…If sandwich complexes of 1‐4 :M n+ = 2:1 for cations whose sizes are larger than the cavity of the crown ether cycle are formed, emission of pyrene excimer may be observed . However, that kind of emission was not observed due to the low concentration of 1‐4 (1.0 × 10 −5 m ).…”

Section: Resultsmentioning

confidence: 99%

“…In investigations carried out recently, we designed and synthesized a variety of functional fluorescent materials that contain the pyrene fluorophore (52)(53)(54)(55)(56)(57)(58)(59)(60)(61)(62)(63). In these studies, we observed that alkynylpyrenes are highly emissive and, as a result, they can be utilized as fluorescent probes for the detection of amino acids, proteins and DNA (53).…”

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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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions

Maeda

Tanaka

Aratani

et al. 2019

Photochem & Photobiology

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“…On the other hand, many studies have been conducted on compounds that link pyrene with crown ethers or oligoethylene glycols as fluorescence sensors that recognize metal ions. 50–92 They can be classified into three types, turn-ON 50–58 and turn-OFF types 59–63 depending on photoinduced electron transfer and heavy atom effect, and monomer/excimer emission switching type 64–84 depending on the spatial distance between two pyrenes.…”

Section: Introductionmentioning

confidence: 99%

(1,6)Pyrenophanes containing crown ether moieties as fluorescence sensors for metal and ammonium ions. Formation of sandwich, dumbbell, and pseudorotaxane complexes

et al. 2023

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“…Pyrene and its derivatives are often used as fluorescent materials because of their photochemical inertness, dual luminescence, and high emission quantum yields. − Especially in recent years, supramolecular chemical sensors based on pyrene monomer-excimer dual luminescence have attracted increasing attention. , Moreover, these sensors have been well applied for the detection of metal ions, − explosives, and biological particles. , However, to our knowledge, there are few reports , about the multiple stimuli -responsive ratiometric sensors based on pyrene.…”

Section: Introductionmentioning

confidence: 99%

Multiple Stimuli-Responsiveness Fluorescent Probe Derived from Cyclopolymers and Pyrene-Ended Ammonium Salts

Wang

Yang

Shi

et al. 2020

ACS Appl. Polym. Mater.

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A multiple stimuli-responsiveness fluorescent probe was fabricated by host-guest recognition between cyclopolymers with larger pseudocrown ether cavities in the backbones and pyrene-ended ammonium salts. Also, this fluorescent probe exhibits ratiometric responsiveness to chloride anions, organic bases, and temperature, as well as a dual luminescence responsiveness to nitro-compounds. These properties of this probe endow it with potential application in multiple stimuliresponsive chemical fluorescence sensors. Moreover, it was found that the cyclopolymers with pyrenes grafted on the backbone increased the excimer/ monomer emission ratio of the fluorescent polypseudorotaxane, which would be expected to present higher sensitivity and responsiveness to an external environment or stimuli-factors.

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Synthesis of pyrenocrown ethers as fluorescent sensors and their recognition ability of metal ions

Cited by 9 publications

References 67 publications

Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions

Ethynylpyrene Linked Benzocrown Ethers as Fluorescent Sensors for Metal Ions

(1,6)Pyrenophanes containing crown ether moieties as fluorescence sensors for metal and ammonium ions. Formation of sandwich, dumbbell, and pseudorotaxane complexes

Multiple Stimuli-Responsiveness Fluorescent Probe Derived from Cyclopolymers and Pyrene-Ended Ammonium Salts

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