55490-87-4

Usage

Uses

Used in Chemical Research:
(9-Anthrylmethylene)malononitrile is used as a fluorescent probe for detecting metal ions due to its unique optical properties, which allow for sensitive and selective detection.
Used in Organic Synthesis:
As a building block in organic synthesis, (9-Anthrylmethylene)malononitrile is utilized for the creation of various organic compounds, contributing to the development of new chemical entities and materials.
Used in Materials Science:
(9-Anthrylmethylene)malononitrile is studied for its potential applications in materials science, where its optical properties could be harnessed to develop advanced materials with specific characteristics.
Used in Photonics:
(9-ANTHRYLMETHYLENE)MALONONITRILE is also being explored for use in photonics, where its unique optical properties may be applied to create innovative photonic devices and systems.

InChI:InChI=1/C18H10N2/c19-11-13(12-20)9-18-16-7-3-1-5-14(16)10-15-6-2-4-8-17(15)18/h1-10H

Upstream product

• 642-31-9 9-anthracene aldehyde 
• 109-77-3 malononitrile 
• 98178-26-8 9-anthracenecarboxaldehyde dimethyl acetal 

Relevant academic research and scientific papers

Binding interactions and FRET between bovine serum albumin and various phenothiazine-/anthracene-based dyes: A structure-property relationship

The present study demonstrates binding interactions and F?rster resonance energy transfer (FRET) between bovine serum albumin (BSA) and a series of structurally and electronically diverse phenothiazine (PTZ) and anthracene (ANT) dyes. Upon selective excitation of tryptophan (Trp) residues of BSA, radiationless energy transfer to a dye takes place, resulting in fluorescence quenching of the former. Fluorescence quenching mechanisms, FRET parameters, possible locations, and binding constants of dyes with the BSA have been examined to deduce a structure-property relationship. The mechanism of quenching is apparently static in nature. PTZ dyes with heteroatoms and a pentyl tail (C5-PTZ) attached to them were found to have a stronger binding affinity with BSA as compared to ANT dyes. Stronger binding affinities of C5-PTZ dyes with BSA result in greater energy transfer efficiencies (ET). A dye with a strong electron-withdrawing group present in it has shown better energy accepting capability. A FRET study with dicyanoaniline (DCA) analogs of PTZ and ANT dyes (C5-PTZDCA and ANTDCA, respectively) revealed that ET depends on electronic and structural factors of molecules. An almost orthogonal geometry between ANT and DCA moieties (～79°) in ANTDCA induces the greater extent of electron transfer from ANT to DCA, showing a higher ET for this dye as compared to C5-PTZDCA in which the torsion angle is only ～38°. Further, the observed facts have been validated by experimentally determined bandgaps (using cyclic voltammetry experiments) for all the dyes. Thus, the hydrophobic character and the presence of interactive substituents along with the electron-accepting abilities majorly control the FRET for such dyes with BSA.

Single-crystalline, size, and orientation controllable nanowires and ultralong microwires of organic semiconductor with strong photoswitching property

Single-crystalline, precise size-controlled nanowires and ultralong microwires with lengths reaching several millimeters of organic semiconductor 1 were prepared in large scale by cast assembly. The size and density of the nanowires and microwires could be controlled by simply adjusting the concentration of 1 in casting solutions. More importantly, the formation of these nanowires and microwires showed no substrate and solvent dependence and was orientation controllable. Highly reproducible and sensitive photo response characteristics were observed in these nanowires and microwires. Fast and reversible photo-switchers based on multiple or individual single-crystal microwires were fabricated via "multi times gold wire mask moving" technique with switch ratio over 100.

Nanochannel-based {BaZn}-organic framework for catalytic activity on the cycloaddition reaction of epoxides with CO2and deacetalization-Knoevenagel condensation

Herein, the rare combination of BaII (5s) and ZnII (3d) in the presence of the structure-oriented TDP6- ligand generated the nanochannel-based hybrid material {[(CH3)2NH2]2[BaZn(TDP)(H2O)]·DMF·5H2O}n (NUC-51, H6TDP = 2,4,6-tri(2,4-dicarboxyphenyl)pyridine), which possesses excellent physicochemical characteristics such as nanoscopic channels, high porosity, large specific surface area, and high heat/water-resistance. To the best of our knowledge, this is the first 3D [BaIIZnII(CO2)6(H2O)]-based nano-porous host framework, whose activated state possesses the coexistence of Lewis acid-base sites including 4-coordinated Zn2+ ions, 7-coordinated Ba2+ ions, uncoordinated carboxyl oxygen atoms, and Npyridine atoms. Catalytic experiments exhibited that activated NUC-51a possesses a high catalytic activity on the cycloaddition reactions of epoxides with CO2 at 55 °C, which can be ascribed to its structural advantages of nanoscale channels and rich bifunctional active sites. Moreover, NUC-51a could significantly accelerate the deacetalization-Knoevenagel condensation reaction in DMSO solvent at 70 °C.

Two new calix[4]resorcinarene-based coordination cages adjusted by metal ions for the Knoevenagel condensation reaction

Two new calix[4]resorcinarene-based coordination cages, namely, [Zn4(TPC4R)(PDC)4]·2DMF·6H2O (1-Zn) and [In11(TPC4R)2(PDC)16(μ2-OH)2(H2O)2]·[(CH

Photoelectrochemical and thermal characterization of aromatic hydrocarbons substituted with a dicyanovinyl unit

Seven aromatic hydrocarbons bearing a dicyanovinyl unit were prepared to determine the relationship between both the number of aromatic rings and location of acceptor substituent on their thermal and optoelectronic properties. Additionally, the density functional theory calculations were performed. The obtained compounds showed temperatures of the beginning of thermal decomposition in the range of 137–289 °C, being above their respective melting points found between 88 and 248 °C. They were electrochemically active and showed quasi-reversible reduction process (except for 2-(phen-1-yl)methylene)malononitrile). Electrochemically estimated energy band gaps were below 3.0 eV, in the range of 2.10–2.50 eV. The absorption and emission spectra were recorded in CHCl3 and NMP and in solid state. All compounds strongly absorbed radiation with absorption maximum ranging from 307 to 454 nm ascribed to the intramolecular charge transfer between the donor and acceptor units. The aromatic hydrocarbons were luminescent in all investigated media and exhibited higher photoluminescence quantum yields in the solid state due to the aggregation induced emission phenomena. Electroluminescence ability of selected compounds was tested in a diode with guest-host configuration. Additionally, the selected compound together with a commercial N719 was applied in the dye-sensitized solar cell.

Bifunctional design of stable metal-organic framework bearing triazole–carboxylate mixed ligand: Highly efficient heterogeneous catalyst for knoevenagel condensation reaction under mild conditions

A highly water stable zinc metal–organic framework (ZnMOF), {[Zn(HL)2]}n, was synthesized using a triazole–carboxylate-based mixed ligand (L = 5-(4H-1,2,4-triazol-4-yl)isophthalic acid). A 2D MOF was formed by hydrothermal synthesis, and extended to a 3D supramolecular network through strong hydrogen bonding. This MOF was fully characterized by Fourier-transformation infrared spectroscopy, thermogravimetric analysis, single-crystal X-ray diffraction (XRD), powder XRD and elemental analysis. Owing to the d10 configuration of this ZnMOF, its luminescent properties were suitable for the sensing of the CN? ions over other anions, as inferred from the florescence result. However, regarding the catalytic mechanism, this ZnMOF showed a strong ability to react with CN?, which might be due to the hydrogen bonding between the COOH groups without coordination. This interaction behavior with CN? ions makes the ZnMOF a promising heterogeneous catalyst for Knoevenagel condensations using malononitrile and aldehyde derivatives as reactants under mild conditions. All reactions were conducted in water as a green solvent.

Effecting structural diversity in a series of Co(ii)-organic frameworks by the interplay between rigidity of a dicarboxylate and flexibility of bis(tridentate) spanning ligands

In a one-pot self-assembly reaction of Co(OAc)2·4H2O, thiophene-2,5-dicarboxylic acid (H2tdc) and four different bis(tridentate) polypyridyl spanning ligands under ambient conditions, a series of structurally diverse metal-organic frameworks has been synt

Design, synthesis and biological evaluation of new series of hexahydroquinoline and fused quinoline derivatives as potent inhibitors of wild-type EGFR and mutant EGFR (L858R and T790M)

New series of hexahydroquinoline and fused quinoline derivatives were designed and synthesized. The thirty seven new compounds were screened for in vitro antitumor activity against HepG2, HCT-116 and MCF-7 cancer cells. Results indicated that compounds 2e

1,4,5,6,7,8-Hexahydroquinolines and 5,6,7,8-tetrahydronaphthalenes: A new class of antitumor agents targeting the colchicine binding site of tubulin

New series of 2-amino-1,4,5,6,7,8-hexahydroquinoline-3-carbonitriles 3a,b and 2-amino-5,6,7,8-tetrahydronaphthalene-1,3-dicarbonitriles 4a-h were synthesized and evaluated for their antitumor activity. In vitro antitumor screening of the new members again

Two Hg(II)-based Macrocycles Offering Hydrogen Bonding Cavities: Influence of Cavity Structure on Heterogeneous Catalysis

We present synthesis and characterization of two Hg-macrocycles offering H-bonding based cavities of varying dimensions. Both Hg-macrocycles illustrate noteworthy difference in their catalytic performance that has been related to their cavity structures.