27287-82-7

Usage

Uses

Used in Organic Synthesis:
(Pyren-1-ylmethylidene)propanedinitrile is utilized as an intermediate in organic synthesis for the creation of various complex organic molecules. Its specific structural features allow for the development of novel compounds with potential applications in different industries.
Used in Materials Science:
In the field of materials science, (pyren-1-ylmethylidene)propanedinitrile is used as a building block for the development of new materials with unique properties. Its incorporation into materials can lead to advancements in areas such as polymer science and composite materials.
Used in Optoelectronic Devices:
(Pyren-1-ylmethylidene)propanedinitrile is also used as a component in the design and fabrication of optoelectronic devices. Its properties make it a promising candidate for applications in organic light-emitting diodes (OLEDs) and organic field-effect transistors (OFETs), where it can contribute to improved performance and functionality.
Ongoing Research:
(pyren-1-ylmethylidene)propanedinitrile's structure and properties make it a promising candidate for various technological applications. As a result, ongoing research is being conducted to explore its potential uses in industry and academia, with the aim of discovering new applications and enhancing its performance in existing ones.

Upstream product

• 3029-19-4 pyrene-1-aldehyde 
• 109-77-3 malononitrile 

Relevant academic research and scientific papers

Microporous coordination polymer [Zn4(dmf)(ur)2(ndc)4] as a heterogeneous catalyst for the Knoevenagel reaction

The catalytic properties of the microporous metal-organic coordination polymer [Zn4(dmf)(ur)2(ndc)4] (dmf is N,N'-dimethylformamide, ur is urotropine, and ndc2- is 2,6-naphthalenedicarboxylate) for the Knoevenagel reaction were studied. The reaction between aromatic aldehydes (benzaldehyde, α-naphthaldehyde, 4-biphenylaldehyde, and 1-pyrenaldehyde) and malononitrile was studied. The coordination polymer was shown to be a heterogeneous catalyst that makes it possible to achieve 95% yield in the reaction between benzaldehyde and malononitrile. The selectivity of the catalyst depends on the size of aldehydes used in the reaction.

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.

Switching on Supramolecular Catalysis via Cavity Mediation and Electrostatic Regulation

Synthetic supercontainers constructed from divalent metal ions, carboxylate linkers, and sulfonylcalix[4]arene-based container precursors exhibit great promise as enzyme mimics that function in organic solvents. The capacity of these artificial hosts to catalyze Knoevenagel condensation can be switched on when the aldehyde substrate possesses a molecular size and shape matching the nanocavity of the supercontainers. In contrast, little reactivity is observed for other aldehydes that do not match the binding pocket. This substrate-dependent catalytic selectivity is attributed to the Br?nsted acidity of the metal-bound water molecules located inside the nanocavity, which is amplified when the size/shape of the aldehyde substrate fits the binding cavity. The electrostatic environment of the binding cavity and the Br?nsted acidity of the supercontainer can be further modulated using tetraalkylammonium-based regulators, leading to higher reactivity for the otherwise unreactive aldehydes.

Effect of electron withdrawing anchoring groups on the optoelectronic properties of pyrene sensitizers and their interaction with TiO2: A combined experimental and theoretical approach

A series of pyrene sensitizers (PC, PN, PMN, PR) with various electron withdrawing anchoring groups have been synthesized to understand their consequence on the optoelectronic properties. All the sensitizers have been characterized by NMR, mass spectroscopic and IR techniques. Absorption measurements revealed that charge transfer transition was enhanced by introducing electron withdrawing groups. Effect of solvents on the absorption and emission properties of the sensitizers was probed through multi-parameter Catalán solvent scales. Thermal stability of the sensitizers was found to be influenced by the presence of COOH group. DFT/TDDFT calculations were performed to gain insight into the structure and electronic properties of the pyrene sensitizers. To investigate the binding affinity of pyrene sensitizers with TiO2, absorption measurement was performed and the results suggest that the sensitizer having COOH group along with a CN group (PC) show higher binding affinity over other sensitizers containing COOH group (PR) and NO2 group (PN). Further, laser flash photolysis measurement was carried out to study the electron transfer process between the sensitizers and TiO2. Electron injection into the conduction band of TiO2 was confirmed by the detection of cation radical of the sensitizer. We envisage that the results from this work will pave the way to design new efficient sensitizers with predetermined electron withdrawing anchoring groups and their photophysical properties for photovoltaic applications.

Intramolecular Charge Transfer Properties of Dicyanovinyl-Substituted Aromatics

A series of five dicyanovinyl (DCV)-substituted aromatic compounds (referred to collectively as Ar-DCV, where Ar = 1-phenyl, 1-naphthyl, 9-anthracenyl, 9-phenanthrenyl, and 1-pyrenyl) were prepared and their ground- and excited-state properties were examined.Solvent-dependent NMR studies indicate that the ground state of the Ar-DCV compounds is polar.Strong intramolecular charge transfer (ICT) absorption bands were observed for each compound.The position of the ICT absorption is nearly independent of solvent polarity and the molar absorptivity is related to the twist angle between the aromatic donor and the DCV acceptor.The fluorescence spectra are highly solvatochromatic and the fluorescence energy correlates with the solvent polarity parameter Δf in a variety of solvents.The fluorescence quantum yields are low and no emission was observed from phenyl-DCV.An excited state model is proposed which explains the solvent dependence of the ICT absorption and emission of the series of Ar-DCV compounds.

Unravelling the effect of anchoring groups on the ground and excited state properties of pyrene using computational and spectroscopic methods

Anchoring groups play an important role in dye sensitized solar cells (DSCs). In order to acquire a suitable anchoring group for DSCs, a deeper understanding of the effect of anchoring groups on the ground and excited state properties of the dye is significant. In this context, various anchoring group connected pyrene derivatives are successfully synthesized and well characterized by using 1H, 13C-NMR, FT-IR and EI-MS spectrometry. The anchoring groups employed are carboxylic acid, malonic acid, acrylic acid, malononitrile, cyanoacrylic acid, rhodanine and rhodanine-3-acetic acid. The optimized geometries, HOMO-LUMO energy gap, light harvesting efficiency (LHE) and electronic absorption spectra of these dyes are studied by using density functional theory (DFT) calculations. The results show that pyrene connected with anchoring groups with weak electron pulling strength (PC, PAC and PMC) has a larger HOMO-LUMO energy gap, whereas that connected with anchoring groups with strong electron pulling strength (PCC, PMN, PR and PRA) has a reduced HOMO-LUMO energy gap. These molecules with a reduced energy gap are primarily preferred for DSC applications. Moreover, P, PC, PAC and PMC molecules undergo π → π? transition, whereas PCC, PMN, PR and PRA molecules show significant charge transfer along with π → π? transition. UV-visible absorption spectral studies on these dyes reveal that connecting various anchoring groups with different electron pulling abilities enables the pyrene chromophore to absorb in the longer wavelength region. Notably, an efficient bathochromic shift is observed for PCC, PMN, PR and PRA molecules in both electronic absorption and fluorescence spectral measurements, which suggests that the excitation is delocalized throughout the entire π-system of the molecules. Both theoretical and spectral studies reveal that dyes with an ICT character (PCC, PMN, PR and PRA) are suitable for dye sensitized solar cell applications.

Organogel media for on-bead screening in combinatorial catalysis

Poly(vinylidene fluoride) (PVdF) forms thermoreversible gels with a number of dipolar aprotic solvents. Gels were prepared containing chromogenic substrates, subject to transformation by polymer-bound catalysts. When the catalysts were mixed with inactive beads and applied to the surface of the gels, the active beads were identifiable through colour changes. Active beads could also be visualised by thermographic imaging. These methods hold promise for catalyst discovery from split-and-mix combinatorial libraries.

Discrete coordination molecule container and preparation method and small molecule catalysis application thereof

The invention relates to a discrete coordination molecule container and a preparation method and application thereof. The structure of the discrete coordination molecule container is [M4 (mu4-B) (X)]6Y6Z2, wherein M is a metal element; b is H2O (water); X is a thiacalix [4] arene ligand; Y is an asymmetric tricarboxylic acid ligand; and Z is a symmetric tricarboxylic acid ligand. The discrete coordination molecule container provided by the invention is provided with a functionally modified inner cavity, a specific nano inner cavity structure realizes enrichment of an organic reaction substrate and enhances contact with catalytic active sites, and meanwhile, an acidic active center of mu4-H2O and an alkaline active center of imino form an acid-base dual catalytic active center. The discrete coordination molecular container provided by the invention is used for homogeneous catalysis of Knoevenagel condensation reaction, and has efficient catalytic activity.

New quinoline- and isoquinoline-based multicomponent methods for the synthesis of 1,1(3,3)-dicyanotetrahydrobenzoindolizines

Convenient multicomponent methods for the synthesis of benzannulated dihydroindolizines based on quinoline or isoquinoline, malononitrile, aromatic aldehydes and α-halomethylcarbonyl compounds were developed. Several alternative protocols of using the reactants were studied, starting with separate generation of two most probable intermediates and ending with the four-component condensation of all reactants. The scope of applicability of these methods was found, depending on the initial compounds used. The reaction is highly stereoselective with predominant formation of one of the possible isomers.

Native and modified chitosan-based hydrogels as green heterogeneous organocatalysts for imine-mediated Knoevenagel condensation

A variety of methylenemalononitriles and ethyl cyanoacrylates derived from both aromatic and heteroaromatic aldehydes were synthesized by Knoevenagel condensation catalysed with native and modified chitosan-based heterogeneous catalysts. The efficiency of our hydrogel organocatalysts, chitosan hydrogel beads and ureidyl-chitosan derivative hydrogel disks, was evaluated as function of pH, temperature and catalyst concentration by considering reaction rates, conversions, E/Z stereoselectivities, and kinetic studies of a model reaction between 4-nitrobenzaldehyde and ethyl cyanoacetate. An unprecedented study by solid state 13C CP MAS NMR of the employed catalyst when reaction was quenched after a 50% of conversion, has demonstrated that an imine-chitosan intermediate is formed during this process. Analysis of E/Z ethyl cyanoacrylate isomer mixtures for determining the corresponding stereoselectivity was carried out by NMR measuring carbon-proton coupling constants (3JC,H) using a novel CLIP-HSQMCB experiment. Additionally, DFT calculations let us rationalise the observed E/Z stereoselectivities as well as to evaluate the role of ureidyl moiety on interaction with aldehydes and imine intermediate formation with chitosan derivative.