Cyclic siloxanes conjugated with fluorescent aromatic compounds as fluoride sensors

Prigyai, Nicha; Chanmungkalakul, Supphachok; Thanyalax, Sutthiroj; Sukwattanasinitt, Mongkol; Ervithayasuporn, Vuthichai

doi:10.1039/d0ma00476f

Cited by 8 publications

(9 citation statements)

References 46 publications

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“…Pyrene derivatives have been very often used to produce luminescent gels with different applications, 4,9,15,[103][104][105] most of them mediated by hydrogen bonding. 4,15,23,106 On the other hand, few but consistent studies proved the ability of bent-core compounds as gelators.…”

Section: Gelation Properties and Photo-physics In The Gel Statementioning

confidence: 99%

Luminescent assemblies of pyrene-containing bent-core mesogens: liquid crystals, π-gels and nanotubes

et al. 2022

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Section: Gelation Properties and Photo-physics In The Gel Statementioning

confidence: 99%

Luminescent assemblies of pyrene-containing bent-core mesogens: liquid crystals, π-gels and nanotubes

et al. 2022

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“…From our previous reports, the SQ cage provides outstanding potential to sense anions. ,, The SQ cage has an empty internal void which could encapsulate anions inside the cage, and the surface of the cage can interact with the anions by electrostatic interaction. Owing to the electron deficiency of the silicon, the interaction between silicon and an anion is possible.…”

Section: Introductionmentioning

confidence: 99%

Mono and Dumbbell Silsesquioxane Cages as Dual-Response Fluorescent Chemosensors for Fluoride and Polycyclic Aromatic Hydrocarbons

et al. 2022

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Pyrene-conjugated monomeric (2) and dimeric (5) shaped-silsesquioxane (SQ) cages, as chemical sensors for detecting fluoride and polycyclic aromatic hydrocarbons (PAHs), were prepared by Heck-coupling reactions between vinyl-functionalized SQ cages and bromo-substituted pyrenes. These sensors give a remarkable deep-blue fluorescence, which could be quenched in the presence of fluoride and electron-withdrawing PAHs. Interestingly, both sensors 2 and 5 show a rapid detection toward PAHs, while a high number of vinylic silicon atoms in a monomeric cage-based sensor 2 detected fluoride relatively faster than a bulky dumbbell sensor 5. In addition, these sensors also provide a naked-eye color of fluoride detection through an intramolecular charge-transfer presenting in yellow and pink (λ max ∼ 495 and 520 nm) for mono and dumbbell sensors, respectively. The limit of detection for fluoride and PAH (e.g., 1pyrenecarboxaldehyde and 1-nitropyrene) detections is approximately 1−3 μM. The computational calculation for the further mechanistic study of PAHs detection revealed that an emission of SQ was absorbed by PAHs, thereby resulting in aggregationcaused quenching.

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“…Recently, cyclosiloxanes having fluorescence moieties with appropriate linkers have been widely studied. Cycloteterasiloxane having naphthyl, anthryl, pyrenyl, − and BODIPY, with alkyl and alkenyl linkers have been prepared. However, cyclosiloxanes in which polycyclic aromatic hydrocarbons such as anthracene and pyrene are directly connected to silicon atoms have scarcely been reported.…”

Section: Introductionmentioning

confidence: 99%

“…West and co-workers reported that fluorescence cyclotri- and tetrasiloxanes contain silafluorene and silole skeletons. Fluorescent properties of a cyclotetrasiloxane having naphthalene diimides via decamethylene spacer and cyclotetrasiloxanes bearing 9-anthrylethenyl and 1-pyrenylethenyl groups , (via ethenyl spacers) have also been reported. Fluorescence and sensing ability of cyclotetrasiloxane-based porous polymers with pyrene, tetraphenylethene, and spirobifulorene were also described by Wang et al Nemoto et al reported that a siloxane-bridged cyclic dimer with 1,6-pyrenylene moieties showed strong excimer emission due to the parallel arrangement of two pyrenyl groups from the restricted cyclophane structure .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Cyclotri- and Tetrasiloxanes with Pyrenyl Groups

et al. 2022

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Cyclosiloxanes directly bearing polyaromatic groups on silicon atoms have scarcely been reported. Herein, hexa(1pyrenyl)cyclotrisiloxane (2) and octa(1-pyrenyl)cyclotetrasiloxane (3) were successfully prepared from di(1-pyrenyl)silanediol (1) in the presence of a weak base such as tetraethylammonium acetate and triethylamine in MeCN. The structure of the cyclosiloxanes bearing multiple pyrenyl groups in the solid and solution states was evaluated by NMR, X-ray crystallography, and density functional theory (DFT) calculations. All pyrenyl groups of 2 were oriented outward, and no π−π stacking of adjacent pyrenyl groups was observed. However, all pairs of adjacent pyrenyl groups at 1-and 3-positions in 3 are oriented in the same direction and were π−π stacked with respect to each other. The UV−vis spectra of 2 and 3 in organic solvents showed a slight broadening of the peaks, as observed for typical pyrene derivatives. Interestingly, the fluorescence spectra of 2 showed small monomer and strong excimer emissions; however, those of 3 showed only a strong excimer emission in all solvents. Partially pyrenylated cyclotri-and tetrasiloxanes (compounds 4 and 5) showed solvent-dependent monomer and excimer spectra as observed for di(1-pyrenyl)silane derivatives, implying that the excimer emissions of 2 and 3 arise from mainly geminal and vicinal pyrenyl groups, respectively.

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Cyclic siloxanes conjugated with fluorescent aromatic compounds as fluoride sensors

Abstract: When cyclic siloxanes were exposed to fluoride ions, a blue-shift and enhanced fluorescence emissions appeared in most organic solvents.

Cited by 8 publications

References 46 publications

Luminescent assemblies of pyrene-containing bent-core mesogens: liquid crystals, π-gels and nanotubes

Luminescent assemblies of pyrene-containing bent-core mesogens: liquid crystals, π-gels and nanotubes

Mono and Dumbbell Silsesquioxane Cages as Dual-Response Fluorescent Chemosensors for Fluoride and Polycyclic Aromatic Hydrocarbons

Synthesis and Characterization of Cyclotri- and Tetrasiloxanes with Pyrenyl Groups

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