Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Isatin-1,8-Naphthalimide Hydrazones: A Study of Their Sensor and ON/OFF Functionality.

ABSTRACT: Five novel hydrazones derived from substituted isatins were synthesized as potential anion sensors. Using UV-VIS, FTIR, NMR and fluorescence spectroscopy, these compounds' tautomeric equilibrium and Z-E photoisomerization were studied in DMF and CHCl?, depending on the hydrazone concentrations, the presence of basic anions and light stimulation. Anion recognition aspects (PF?-, HSO?-, Br-, Cl-, NO?-, F- and CH?COO-) and these receptors' detection limits were also studied. We also tested the light-stimulated ON-OFF functionality of these compounds in the presence or absence of these anions.

SUBMITTER: Tisovsky P

PROVIDER: S-EPMC6385022 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Isatin-1,8-Naphthalimide Hydrazones: A Study of Their Sensor and ON/OFF Functionality.

Tisovský Pavol P Horváth Miroslav M Csicsai Klaudia K Donovalová Jana J Filo Juraj J Cigáň Marek M Sokolík Róbert R Addová Gabriela G Gáplovský Anton A

Molecules (Basel, Switzerland) 20190122 3

Five novel hydrazones derived from substituted isatins were synthesized as potential anion sensors. Using UV-VIS, FTIR, NMR and fluorescence spectroscopy, these compounds' tautomeric equilibrium and Z-E photoisomerization were studied in DMF and CHCl₃, depending on the hydrazone concentrations, the presence of basic anions and light stimulation. Anion recognition aspects (PF₆-, HSO₄-, Br-, Cl-, NO₃-, F- and CH₃COO<su ...[more]

PMID: 30678292

Similar Datasets

ON/OFF Photostimulation of Isatin Bipyridyl Hydrazones: Photochemical and Spectral Study.

Project description:Four novel isatin hydrazones containing bipyridyl fragments were synthesized as potential ON/OFF switches. Hydrazone Z-isomers exhibit high thermal stability. The characteristic photochemical reaction for all studied hydrazones is the Z-E isomerization in CHCl3. After irradiation of hydrazones 1 and 2 in dimethylformamide (DMF), the photoreaction products are tautomers. When using light with the appropriate wavelength, the photo-tautomerization reaction is reversible. In these conditions, studied hydrazones have ON/OFF switch properties. In the case of hydrazones 1 and 2, by alternating heat and light stimulation it is possible to control the isomerization process reversibly. In the presence of fluoride ions, NH hydrogen from the studied hydrazones is cleaved, and the corresponding anions are formed. The resulting anions of Z-isomers are changed to the corresponding E-isomer at room temperature.

| S-EPMC6680666 | biostudies-literature

N-(4-Chloro-phenyl)-1,8-naphthalimide.

Project description:In the title compound, C(18)H(10)ClNO(2), the naphthalimide ring system is almost planar, the rings forming dihedral angles of 2.05?(3), 2.26?(3) and 0.80?(3)°. The attached benzene ring of the 4-chloro-phenyl substituent is inclined to the mean plane of the naphthalimide ring system by 75.77?(11)°. In the crystal structure, symmetry-related mol-ecules are linked by C-H?O inter-actions. There are also weak ?-? contacts between the naphthalimide rings [centroid-centroid distance = 3.732?(3)?Å].

| S-EPMC2969255 | biostudies-literature

N-(2-Hydroxy-ethyl)-1,8-naphthalimide.

Project description:In the mol-ecule of the title compound, C(14)H(11)NO(3), the naphthalimide ring system is nearly planar (r.m.s. deviation 0.0139 Å). In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers forming R(2) (2)(14) ring motifs. π-π contacts between the naphthalimide rings [centroid-centroid distances = 3.648 (3), 3.783 (3), 3.635 (3), 3.722 (3) and 3.755 (3) Å] may further stabilize the structure.

| S-EPMC2969747 | biostudies-literature

Synthesis and Fluorescent Property Study of Novel 1,8-Naphthalimide-Based Chemosensors.

Project description:A series of novel mono- and di-substituted N-n-butyl-1,8-naphthalimide derivatives were synthesized simultaneously via a three-step reaction. The single crystal structure of N-n-butyl-4-[N',N'-bis(2',4'-dichlorobenzoyl)ethylamino]-1,8-naphthalimide (3f) was determined. The UV-vis and fluorescence properties of compound 3f were investigated. The 3f showed highly selective and sensitive fluorescence changes response towards Pb2+. A titration of monomer with Pb2+ ion was performed. When Pb2+ ion concentration increased from 0 to 10 eq., the fluorescent intensity of 3f decreased from 199.97 to 48.21. The pH effect on 3f showed that it is stable in a wide range of pH. The results indicated that 3f might be a probe molecule for Pb2+.

| S-EPMC6017435 | biostudies-literature

N-(4-Amino-phen-yl)-1,8-naphthalimide hemihydrate.

Project description:The title compound, C(18)H(12)N(2)O(2)·0.5H(2)O, was prepared by the reaction of 1,4-phenyl-enediamine with 1,8-naphthalic anhydride in refluxing dimethyl-formamide. The structure is stabilized by N-H?O and O-H?O hydrogen bonds. There are ?-? stacking inter-actions [centroid-centroid distances of 3.718?(2), 3.510?(2) and 3.546?(2)?Å] and C-H?? inter-actions between the mol-ecules. The water molecule lies on a twofold rotation axis. Its two H atoms are disordered equally over two positions.

| S-EPMC2915319 | biostudies-literature

N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide.

Project description:In the title compound, C(21)H(20)N(2)O(3), the naphthalimide unit is almost planar (r.m.s. deviation for the 15 non-H atoms = 0.059?Å). The carboximide N atom and the five C atoms of the 2-methyl-prop-2-enoyl substituent also lie in a plane (r.m.s. deviation = 0.009?Å), which subtends an angle of 84.34?(7)° to the naphthalamide plane. This orients the =CH(2) group of the vinyl fragment towards the naphthalimide rings, giving the mol-ecule an extended configuration. The piperidine ring adopts a chair conformation and there is evidence for some delocalization between the naphthalene and piperidine units, the C-N(pip) bond length being 1.404?(4)?Å. In the crystal structure, ?-? contacts with centroid-centroid distances of 3.5351?(18) and 3.7794?(18)?Å supported by C-H?O hydrogen bonds link adjacent mol-ecules in a head-to-tail fashion, forming dimers. These are further stabilized by other C-H?O contacts of varying strength, which stack the mol-ecules down the b axis.

| S-EPMC2979536 | biostudies-literature

A simple sensor based on 1,8-naphthalimide with large Stokes shift for detection of hypochlorous acid in living cells.

Project description:Hypochlorous acid (HOCl), one of the most reactive and deleterious reactive oxygen species (ROS), plays a vital role in many pathological and physiological processes. However, as a result of the highly reactive and diffusible nature of HOCl, its uncontrolled production may lead to an adverse effect on host physiology. Because of its biological importance, many efforts have been focused on developing selective fluorescent probes to image HOCl. However, it is still challenging to design a fluorescent probe with exclusive selectivity towards HOCl. In this study, a novel fluorescent probe for HOCl, Probe 1 was rationally designed based on 1,8-naphthalimide. As the concentration of HOCl increased, the fluorescence intensity of the probe gradually decreased, and the solution color changed from yellow-green to colorless, indicating this is a "naked-eye sensor". Probe 1 has a large Stokes shift (120 nm), which can effectively avoid fluorescence self-absorption. In addition, Probe 1 shows excellent selectivity to HOCl among different ions including common ROS, high sensitivity, fast response (<2 min), high fluorescence quantum yield (Φ = 0.93) and low detection limit (0.237 μM). Finally, the imaging results in HeLa cells showed that the probe could be used for the detection of exogenous and endogenous HOCl, and proved the potential of the probe as a biosensor for the detection of HOCl.

| S-EPMC9072363 | biostudies-literature

New Acceptor-Donor-Acceptor Systems Based on Bis-(Imino-1,8-Naphthalimide).

Project description:In this paper, six novel symmetrical bis-(imino-1,8-naphthalimides) differing in core and N-substituent structure were synthesized, and their thermal (TGA, DSC), optical (UV-Vis, PL), electrochemical (DPV, CV) properties were evaluated. The compounds were stable to 280 °C and could be transferred into amorphous materials. Electrochemical investigations showed their ability to occur reductions and oxidations processes. They exhibited deep LUMO levels of about -3.22 eV and HOMO levels above -5.80 eV. The optical investigations were carried out in the solutions (polar and non-polar) and in films and blends with PVK:PBD. Bis-(imino-1,8-naphthalimides) absorbed electromagnetic radiation in the range of 243-415 nm and emitted light from blue to yellow. Their capacity for light emission under voltage was preliminarily tested in devices with an active layer consisting of a neat compound and a blend with PVK:PBD. The diodes emitted green or red light.

| S-EPMC8196752 | biostudies-literature

The Synthesis and Antitumor Activity of 1,8-Naphthalimide Derivatives Linked 1,2,3-Triazole.

Project description:In this study, acenaphthylene was used as the raw material, and a series of novel 1,8-naphthalimide-1,2,3-triazole derivatives was obtained through oxidation, acylation, alkylation, and click reactions, and subsequently, their anti-tumor activities were tested. After screening, we found that Compound 5e showed good activity against H1975 lung cancer cells, with the half maximal inhibitory concentration (IC50) reaching 16.56 μM.

| S-EPMC8076741 | biostudies-literature

Luminescence and Electrochemical Activity of New Unsymmetrical 3-Imino-1,8-naphthalimide Derivatives.

Project description:A new series of 1,8-naphtalimides containing an imine bond at the 3-position of the naphthalene ring was synthesized using 1H, 13C NMR, FTIR, and elementary analysis. The impact of the substituent in the imine linkage on the selected properties and bioimaging of the synthesized compounds was studied. They showed a melting temperature in the range of 120-164 °C and underwent thermal decomposition above 280 °C. Based on cyclic and differential pulse voltammetry, the electrochemical behavior of 1,8-naphtalimide derivatives was evaluated. The electrochemical reduction and oxidation processes were observed. The compounds were characterized by a low energy band gap (below 2.60 eV). Their photoluminescence activities were investigated in solution considering the solvent effect, in the aggregated and thin film, and a mixture of poly(N-vinylcarbazole) (PVK) and 2-tert-butylphenyl-5-biphenyl-1,3,4-oxadiazole (PBD) (50:50 wt.%). They demonstrated low emissions due to photoinduced electron transport (PET) occurring in the solution and aggregation, which caused photoluminescence quenching. Some of them exhibited light emission as thin films. They emitted light in the range of 495 to 535 nm, with photoluminescence quantum yield at 4%. Despite the significant overlapping of its absorption range with emission of the PVK:PBD, incomplete Förster energy transfer from the matrix to the luminophore was found. Moreover, its luminescence ability induced by external voltage was tested in the diode with guest-host configuration. The possibility of compound hydrolysis due to the presence of the imine bond was also discussed, which could be of importance in biological studies that evaluate 3-imino-1,8-naphatalimides as imaging tools and fluorescent materials for diagnostic applications and molecular bioimaging.

| S-EPMC8509721 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data