Synthesis, crystal structure and complexation with dibenzylammonium ion of a novel class of crownophanes containing bridged fragments of fluorenone and stilbene

Luk’yanenko, N. G.; Kirichenko, T. I.; Lyapunov, A. Yu.; Kulygina, Catherine Yu.; Simonov, Yurii A.; Fonarı, Marina S.; Botoshansky, Mark

doi:10.1016/j.tetlet.2004.02.061

Cited by 13 publications

(7 citation statements)

References 18 publications

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“…Methods.-All the products were purified using silica gel column chromatography, either conventional or flash chromatography. 1 H and 13 C NMR spectra were acquired using BRUKER AVANCE 500 MHz and 150 MHz equipment, with tetramethylsilane (TMS) as an internal standard and chemical shifts (δ) were reported in ppm scale. A Perkin-Elmer Spectrum RX1 FTIR instrument was used to generate Fourier transform infrared (FTIR) spectra in transmittance mode in the range of wave number 400-4000 cm −1 .…”

Section: Methodsmentioning

confidence: 99%

“…The structure of chemosensor NS was confirmed by spectroscopic analysis viz. FTIR, 1 H-NMR, 13 C-NMR spectroscopies (Figs. S1-S3).…”

Section: Methodsmentioning

confidence: 99%

“…Fluorenones based materials have recently sparked significant interest in a variety of applications including electrochemical sensors due to their unique properties including highly polarized extended aromatic system and the presence of the carbonyl oxygen which act as a powerful H-acceptor. 13 The fluorenones provide better recognition sites with ability to easily manoeuvre the surface functional groups and thus pave a way for better specificity of sensor. Mano et al had utilized 2,5,7-trinitro-9fluorenone-4-carboxylic acid to assist the electro-catalytic oxidation of Nicotinamide adenine dinucleotide (NAD + /NADH) by using divalent cation as a bridging unit.…”

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confidence: 99%

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Fluorenone Decorated RGO Based Electrochemical Sensor for Rapid Detection of Chlorpyrifos in Vegetable and Soil Samples

Neha¹,

Kaur²,

Kumari³

et al. 2023

J. Electrochem. Soc.

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A novel synthetically accessible electrochemical sensor has been developed for the detection of chlorpyrifos (CPS) at a very minimal level by utilizing a glassy carbon electrode (GCE) modified with RGO functionalized fluorenone derivative (RGO-NS). The structural and morphological aspects of the derived composite were assessed by Fourier transform infrared spectroscopy, X-ray diffraction, field-emission scanning electron microscopy, and density functional theory with in-depth electrochemical analysis. The fluorenone appended with distinct functionalities has supported the reversible redox reactions of CPS, thus, boosting the specificity of the sensor. The design of the electrochemical sensors involved functionalization of RGO possessing high adsorption capacity, which has further amplified the electrochemical sensitivity. The sensing response has been credited to the reduction associated with hydrogen ion which on addition of CPS gets quenched due to catalytic reaction between the two. The synergy has resulted in the low detection limit of 8.89 ng ml-1 for CPS along with reliable detection of CPS in soil samples without spiking. The framework has the excellent future prospects in the practical management of pernicious pesticides usually employed in agricultural fields and their residues on food products posing a serious danger to human health.

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Section: Methodsmentioning

confidence: 99%

“…The structure of chemosensor NS was confirmed by spectroscopic analysis viz. FTIR, 1 H-NMR, 13 C-NMR spectroscopies (Figs. S1-S3).…”

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Fluorenone Decorated RGO Based Electrochemical Sensor for Rapid Detection of Chlorpyrifos in Vegetable and Soil Samples

Neha¹,

Kaur²,

Kumari³

et al. 2023

J. Electrochem. Soc.

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“…As examples, fluorenones have been described as central units in polymeric electronic devices, [1] incorporated as hosts in catenanes, [2] cyclophanes [3] or crownphanes, [4] as the pendant arm on porphyrins, [5] or even as sensitizers in photoinduced synthesis of PAHs. Such motifs have been described in numerous recent papers dealing with material sciences or potent biologically active compounds.…”

Section: Introductionmentioning

confidence: 99%

A Flexible Strategy Towards Thienyl‐, Oxazolyl‐ and Pyridyl‐Fused Fluorenones

et al. 2013

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The preparation of new thienyl‐, oxazolyl‐, and pyridyl‐fused benzo[c]fluorenones has been developed from a unique and easily available common precursor. Starting from bromotetralone, a short sequence allowed the construction of various heterocycles followed by Suzuki coupling and final acid‐promoted formation of the central cyclopentanone unit. The flexible strategy allowed the selective preparation of fused penta‐ to hepta‐cyclic architectures. Fully aromatic targets have been obtained through the application of an oxidation process. The influence of structural modulations on the photophysical properties are described.

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“…Because of this, cyclophanes are widely used in membrane transport and as catalysts, sen sors, and components of catenanes and rotaxanes that are prototypes of molecular machines and nanoelectronic devices. 7- 15 Recently, [16][17][18][19][20][21][22] we have described the syntheses and properties of first representatives of fluorenonophanes containing two fluorenone fragments or the fluorenone and stilbene fragments linked by flexible polyether chains or conformationally rigid p xylylene bridges. We have demonstrated that fluorenonophanes form stable inclu sion complexes with electron deficient organic mol ecules 16-20 and are promising templates for self assembly of [2]catenanes on their basis.…”

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confidence: 99%

Synthesis and properties of first representatives of crownophanes containing the f luorenone and naphthalene fragments

2007

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A new family of crownophanes containing the fluorenone and naphthalene fragments linked by oligo(oxyethylene) bridges were synthesized. Reactions of these ligands with the paraquat dication gave inclusion complexes of the pseudorotaxane type that were detected by FAB mass spectrometry, 1 H NMR spectroscopy, and electronic absorption spectroscopy.Design, synthesis, and application of various macro cyclic receptors that can selectively discriminate between metal ions, anions, and organic molecules belong to the main problems of the chemistry of "guest-host" com plexes. Cyclophanes, which are macrocycles containing two or more aromatic fragments linked by various bridges, hold a central position among such receptors. 1-6 The size, shape, charge, and hydrophobicity of a cyclophane, as well as its tendency toward various intermolecular in teractions with a guest molecule, can be easily changed by introduction in the receptor structure of rationally se lected aromatic fragments, bridges between them, and functional groups, which allows effective control of its complexing properties. Because of this, cyclophanes are widely used in membrane transport and as catalysts, sen sors, and components of catenanes and rotaxanes that are prototypes of molecular machines and nanoelectronic devices. 7-15Recently, 16-22 we have described the syntheses and properties of first representatives of fluorenonophanes containing two fluorenone fragments or the fluorenone and stilbene fragments linked by flexible polyether chains or conformationally rigid p xylylene bridges. We have demonstrated that fluorenonophanes form stable inclu sion complexes with electron deficient organic mol ecules 16-20 and are promising templates for self assembly of [2]catenanes on their basis. 21,22Here we describe the synthesis and properties of new crownophanes containing the fluorenone and naphtha lene fragments connected by oligo(oxyethylene) chains with different lengths.Crownophanes 1a-d were obtained as shown in Scheme 1.Alkylation of 2,7 dihydroxy 9H fluoren 9 one 2 23 with oligo(ethylene glycol) chlorohydrins 3a-d in DMF in the presence of K 2 CO 3 or in EtOH in the presence of KOH gave diols 4a-c or 4d in 78-80% yields. Reactions of these diols with p toluenesulfonyl chloride in a mixture of 1,4 dioxane and chloroform in the presence of Et 3 N at 0-5 °C for 30 h afforded ditosylates 5a-d in good yields (70-88%). The latter reacted with 1,5 dihydroxy naphthalene 6 at high dilution in DMF in the presence of K 2 CO 3 . After workup of the reaction mixture and puri fication by column chromatography, we obtained fluore none containing crownophanes 1a-d in moderate yields. The yield of the smallest crownophane 1a was low; the yields of crownophanes 1b-d were virtually independent of the ring size.The 1 H NMR spectra of crownophanes 1a-d show a set of signals at δ 3.65-4.38, which are typical of oligo(ethylene glycol) fragments, a characteristic set of signals (two doublets and a doublet of doublets) for the fluorenone protons, and a triplet and two doublets ...

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Synthesis, crystal structure and complexation with dibenzylammonium ion of a novel class of crownophanes containing bridged fragments of fluorenone and stilbene

Cited by 13 publications

References 18 publications

Fluorenone Decorated RGO Based Electrochemical Sensor for Rapid Detection of Chlorpyrifos in Vegetable and Soil Samples

Fluorenone Decorated RGO Based Electrochemical Sensor for Rapid Detection of Chlorpyrifos in Vegetable and Soil Samples

A Flexible Strategy Towards Thienyl‐, Oxazolyl‐ and Pyridyl‐Fused Fluorenones

Synthesis and properties of first representatives of crownophanes containing the f luorenone and naphthalene fragments

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