13755-95-8Relevant articles and documents
Selective chromogenic detection of cyanide in aqueous solution – Spectral, electrochemical and theoretical studies
Lakshmi, P. Raja,Jayasudha,Elango, Kuppanagounder P.
, p. 318 - 323 (2019)
A bisimidazole ensemble (R) possessing naphthoquinone as signaling unit is synthesized and characterized using 1H and 13C NMR and LC-MS spectral techniques. Anion sensing behaviour of the receptor has been investigated using electronic and fluorescence spectral techniques. The receptor exhibits a striking colour change from yellow to brown selectively with cyanide in aqueous HEPES buffer-DMSO (1:1 v/v) medium with a detection limit of 1 μM. Job's continuous variation method suggests that the stoichiometry of the interaction is 1:2 (R:CN?). The binding constant for receptor-cyanide complex was found to be 8.7 × 102 M?1. The mechanism of detection of cyanide occurs via deprotonation of imidazole N-H protons, which is well supported by electrochemical study. DFT based theoretical calculations shows that the energy gap between HOMO and LUMO decreases from 3.3086 (in R) to 1.7799 eV (in R + CN?), which is responsible for the red-shift observed in the UV–Vis spectrum of R upon addition of cyanide ions. The present quinone-bisimidazole based receptor shows few advantages over similar bisimidazoles reported elsewhere.
New naphthoquinone-imidazole hybrids: Synthesis, anion recognition properties, DFT studies and acid dissociation constants
Nural, Yahya,Kele?, Ergin,Ayd?ner, Burcu,Sefero?lu, Nurgül,Atabey, Hasan,Sefero?lu, Zeynel
, (2021)
The two new naphthoquinone-imidazole based dyes containing indole and pyrene moiety were synthesized and their molecular structures were confirmed by FT-IR, 1H/13C NMR, and HRMS. The anion selectivity and sensitivity of dyes were studied with selected TBA salts in DMSO and binary mixture DMSO:Water (1:1, v/v). These interaction mechanisms were verified by spectrophotometric, spectrofluorometric, and 1H NMR titration methods. While the both dyes interact with F?, AcO?, CN?, and H2PO4? in DMSO, only CN? interact with dyes in the aqueous solution. In addition, the experimental results were explained by DFT calculations. The acid dissociation constants of the dyes were determined in 25.0 ± 0.1 °C, 0.1 M NaCl ionic strength in 40% (v/v) DMSO-Water aqueous solution, and acid dissociation constants relating protonated carbonyl group and nitrogen atoms were determined for each dye.
Long-Life, High-Rate Lithium-Organic Batteries Based on Naphthoquinone Derivatives
Lee, Joungphil,Kim, Hoon,Park, Moon Jeong
, p. 2408 - 2416 (2016)
We report the facile synthesis of new naphthoquinone (NQ) derivatives for use in lithium-organic batteries to improve performance. The rational design of these NQ derivatives is based on theoretical calculations. Our lithium-organic batteries demonstrate remarkable charge-discharge properties, for example, a high discharge capacity of 250 mAh g-1 (363 mAh cm-3), discharge potential plateaus in the range of 2.3-2.5 V, and 99% capacity retention after 500 cycles at 0.2C. In particular, the batteries had excellent rate performance up to 50C with reversible redox behavior, unlike most other organic cathode materials. The key to success was a simple molecular substitution, addition of amino groups at the 2- and 3- positions of the NQ ring, yielding 2,3-diamino-1,4-naphthoquinone (DANQ). DANQ has an exceptionally low band gap of 2.7 eV and greater than 20-fold enhancement in the lithium diffusion rate compared to unmodified NQ. The fundamental shortcoming of the organic molecules, i.e., their solubility in the electrolyte, was resolved by covalent linking of the amino groups to the surfaces of the cathode framework. The cyclization of amino groups in DANQ yielded 1H-naphtho[2,3-d]imidazole-4,9-dione (IMNQ), enabled us to achieve a 0.15 V enhancement in the redox potential owing to the delocalized electron distribution in the heteroaromatic ring. Our work suggests that NQ derivatives with modulated charge/ion transport properties are a viable alternative to the more widely studied lithium metal oxides.
A diquinone-imidazole ensemble for selective colorimetric sensing of cyanide in aqueous medium via anion induced NIR absorption
Jayasudha, Palanisamy,Manivannan, Ramalingam,Elango, Kuppanagounder P.
, p. 25473 - 25479 (2016)
A diquinone-imidazole ensemble (R) is rationally designed, synthesized and employed as a selective and sensitive colorimetric sensor for cyanide ions in DMSO:H2O (1:4 v/v). 1H NMR titration indicates that the mechanism of sensing involves the formation of a H-bond between CN- and imidazole N-H. As rationalized, the R-CN- complex exhibited intense NIR-absorption (913 nm; logε 4.3) with a 428 nm red-shift from the absorbance maximum of free R. DFT calculations indicate that the R-CN- complex is perfectly planar with a HOMO-LUMO energy gap of 0.9826 eV which is optimal for NIR-absorption.
Spectroscopic, electrochemical and theoretical studies on anion recognition by receptors with redox active ferrocene and quinone centers bridged by imidazole
Satheshkumar, Angupillai,Manivannan, Ramalingam,Elango, Kuppanagounder P.
, p. 98 - 106 (2014)
Two chromogenic sensors possessing two redox-active centers (quinone and ferrocene) bridged by imidazole anion recognition group have been synthesized and screened for their anion sensing properties. Both the receptors exhibited dramatic color change upon the addition of fluoride and cyanide ions so that we could finish anion recognition by visual detection without resorting to any spectroscopic instruments. The evaluation of the receptor interaction with anions was performed by UV-Vis titration experiments in DMSO. UV-Vis titrations revealed that receptor 1, wherein the imidazole moiety is directly attached to naphthoquinone unit, exhibited a relatively larger bathochromic shift of the intramolecular charge transfer (ICT) band than 2 in which the imidazole receptor unit is away from the quinone moiety. Receptor 1 displays a higher (Δδ = 0.269, 0.352 ppm) downfield shift of the imidazole N-H proton than 2 (Δδ = 0.070, 0.122 ppm) indicating that the anion binding pattern of these chemosensors was H-bond interaction. Also, the UV-Vis and 1H NMR results indicated that the receptor-CN- binding is relatively stronger than receptor-F- interaction. The redox activities of the quinone and ferrocenyl centers in 1 and 2 have been characterized by cyclic and differential pulse voltammetries. Electrochemical titrations revealed that the receptor 1 sensed CN- ions with an anodic shift of -198 mV in the oxidation potential of ferrocene moiety when compared to -188 mV with the receptor 2. Addition of incremental amounts of F- and CN- ions, to these two receptors, shifts the E 1/2 of the quinone redox couple to less negative potentials. DFT (B3LYP/3-21G) calculations performed for both free receptor and receptor-anion complexes are in good agreement with the observed spectroscopic and electrochemical data.
Novel highly functionalized 1,4-naphthoquinone 2-iminothiazole hybrids: Synthesis, photophysical properties, crystal structure, DFT studies, and anti(myco)bacterial/antifungal activity
Gemili, Muge,Nural,Kele?,Ayd?ner,Sefero?lu, Nurgül,ülger, Mahmut,?ahin,Erat,Sefero?lu, Zeynel
, p. 536 - 546 (2019)
In this paper, a series of novel highly functionalized 1,4-naphthoquinone 2-iminothiazole hybrids were synthesized via a cyclization reaction of 2,3-diaminonaphthalene-1,4-dione N-aroylthioureas and α-bromoketones in good to excellent yields (74–94%). The
Are N,N-dihydrodiazatetracene derivatives antiaromatic?
Miao, Shaobin,Brombosz, Scott M.,Schleyer, Paul V R.,Wu, Judy I.,Barlow, Stephen,Marder, Seth R.,Hardcastle, Kenneth I.,Bunz, Uwe H. F.
, p. 7339 - 7344 (2008)
The synthesis and X-ray characterization of two new dialkynylated diazatetracenes and the corresponding N,N-dihydrodiazatetracenes are reported. The dialkynylated heteroacenes are packed in a brick-wall motif that enforces significant overlap of their π-faces. Cyclic voltammetry indicates that the dehydrogenated forms are easily reduced to their radical anions in solution. The planarity of these species validates the discussion of their aromaticity. Nucleus Independent Chemical Shift (NICS) computations demonstrate that both of these 20 π and 24 π electron systems are aromatic. Both experimental and computational results suggest that the aromaticity of the dihydroheteroacenes is reduced.
Design, synthesis and characterization of indole based anion sensing receptors
Manivannan, Ramalingam,Satheshkumar, Angupillai,El-Mossalamy, El-Sayed H.,Al-Harbi, Laila M.,Kosa, Samia A.,Elango, Kuppanagounder P.
, p. 3936 - 3947 (2015)
The design and synthesis of six new receptors (R1-R6) and their anion sensing properties through multiple channels are reported. These receptors are constructed in such a way that they possess indole groups as the binding sites and different acceptors units of varying electron acceptor strengths. Receptors R1, R3 and R5 could recognize fluoride ions visually and spectroscopically with high selectivity over other anions in DMF, which was demonstrated by a visual detection experiment and UV-Vis, fluorescence and 1H NMR spectral studies. The remaining three receptors (R2, R4 and R6) exhibited colour changes with both fluoride and cyanide ions. The binding constants for fluoride binding by these receptors were determined to be in the order of 104 to 106 M-1 and found to depend on the electron accepting property of the acceptor unit in the intra molecular charge transfer (ICT) transition existing with the indole donor units. 1H NMR titration experiments not only provide evidence for the existence of H-bonding interactions between the indolic N-H groups of these receptors and F-, but also offer key insight into the strengths of the receptor-anion complexes of stoichiometry 1:2. The higher fluoride binding ability of the receptor containing the naphthoquinone signalling unit has been interpreted in terms of the greater electron deficiency of the acceptor unit (quinone) and enhanced H-bond donating character of the indole N-H group. The results of the electrochemical and DFT computation studies corroborate well with the spectroscopic studies.
A fused donor-acceptor system based on an extended tetrathiafulvalene and a ruthenium complex of dipyridoquinoxaline
Chesneau, Bertrand,Hardouin-Lerouge, Marie,Hudhomme, Pietrick
, p. 4868 - 4871 (2010)
An application of the Horner-Wadsworth-Emmons reaction carried out on a ruthenium compound as the electrophilic precursor is described for the synthesis of fused donor-acceptor system 1 based on an extended tetrathiafulvalene and a ruthenium complex of dipyridoquinoxaline units.
High-capacity metal ion battery organic electrode material, and preparation method and application thereof
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Paragraph 0043-0045, (2021/06/21)
The invention belongs to the field of ion battery electrode materials, and particularly relates to a high-capacity metal ion battery organic electrode material, and a preparation method and application thereof. The metal ion battery organic electrode material is an organic conjugated compound containing hexaazabenzene and a quinone functional group, the organic conjugated compound contains a plurality of redox active sites, and the theoretical capacity is greater than 500mAh g. The novel conjugated organic electrode material is obtained by carrying out dehydration condensation on the quinonoid compound of o-phenylenediamine and cyclohexanehexone. When the obtained conjugated organic electrode material is used as an aqueous zinc ion battery, high-specific-capacity output and excellent cycling stability and rate capability are realized, and the capacity reaches up to 430 mAh g under the current density of 100 mA g. The conjugated organic material designed by the invention solves the technical problems of lower capacity and poorer rate capability when the existing organic material is used as a zinc ion battery electrode material, and is expected to be used in the field of next-generation environment-friendly and high-energy-density energy storage batteries.
