15058-15-8

Usage

Uses

Used in Fragrance and Flavor Industry:
Propanedinitrile, (2-methyl-4H-1-benzopyran-4-ylidene)is used as a fragrance and flavoring agent for its sweet and hay-like scent. It is widely utilized in perfumes, soaps, and cosmetics to provide a pleasant and distinctive aroma.
Used in Medicinal Applications:
Propanedinitrile, (2-methyl-4H-1-benzopyran-4-ylidene)is being researched for its potential medicinal properties, such as anti-inflammatory, anti-coagulant, and anti-cancer effects. Its diverse pharmacological activities make it a promising candidate for the development of new therapeutic agents.
Used in Research and Development:
Due to its unique chemical structure and properties, Propanedinitrile, (2-methyl-4H-1-benzopyran-4-ylidene)is used in research and development for the synthesis of various coumarin derivatives and other related compounds. This contributes to the advancement of scientific knowledge and the discovery of new applications in different fields.

Upstream product

• 5751-48-4 2-methylchromone 
• 109-77-3 malononitrile 
• 51138-52-4 2-methylbenzopyran-4-thione 
• 7250-94-4 o-acetoxyacetophenone 
• 85-90-5 3-methylchromone 
• 90-02-8 salicylaldehyde 
• 16636-62-7 1-(2'-hydroxyphenyl)butane-1,3-dione 
• 118-93-4 o-hydroxyacetophenone 
• 141-78-6 ethyl acetate 
• 88912-80-5 4-Diphenylmethylene-2-methyl-4H-1-benzopyran 
• 88912-82-7 9-(2-Methyl-4H-1-benzopyran-4-ylidene)-9H-xanthene 

Downstream Products

• 1357262-52-2 (E)-diethyl 2,2'-((4-(2-(4-(dicyanomethylene)-4H-chromen-2-yl)vinyl)phenyl)azanediyl)diacetate 
• 1430329-72-8 (E)-2-(2-(4-azidostyryl)-4H-chromen-4-ylidene)malononitrile 
• 1430329-73-9 2-(2-((E)-4-aminostyryl)-4H-chromen-4-ylidene)malononitrile 
• 1470308-67-8 C₂₀H₁₃N₃O 

Relevant academic research and scientific papers

Molecular Chemiluminescent Probes with a Very Long Near-Infrared Emission Wavelength for in Vivo Imaging

Chemiluminescence imaging is imperative for diagnostics and imaging due to its intrinsically high sensitivity. To improve in vivo detection of biomarkers, chemiluminophores that simultaneously possess near-infrared (NIR) emission and modular structures amenable to construction of activatable probes are highly desired; however, these are rare. Herein, we report two chemiluminophores with record long NIR emission (>750 nm) via integration of dicyanomethylene-4H-benzothiopyran or dicyanomethylene-4H-benzoselenopyran with dioxetane unit. Caging of the chemiluminophores with different cleavable moieties produces NIR chemiluminescence probes (NCPs) that only produce signals upon reaction with reactive oxygen species or enzymes, for example, β-galactosidase, with a tissue-penetration depth of up to 2 cm. Thus, this study provides NIR chemiluminescence molecular scaffolds applicable for in vivo turn-on imaging of versatile biomarkers in deep tissues.

An I6P7 peptide modified fluorescent probe for bio-imaging

The I6P7 peptide was proved to specifically bind to the interleukin-6 receptor, which can be exploited as an effective tumor-targeting moiety. Herein, a novel tumor-targeting fluorescent probe (DMP) conjugated with the I6P7 peptide was designed and synthesized. This probe was validated to possess valuable photophysical properties. The biocompatibility was evaluated by investigating its cytotoxicity on HUVEC and U87 cells, respectively. The tumor cell affinity has been confirmed by bio-imaging of this probe on different human cancer cells (U87, A549 and MCF-7 cells) and normal cells (HUVEC cell). The probe demonstrates low cytotoxicity, high tumor cell affinity and favorable mitochondria-targeting capability. Overall, these results revealed that DMP can serve as an important fluorescent probe for tumor-targeted bio-imaging.

New chromophores based on 2-(4-vinylchromen-2-ylidene)malononitrile and 2-(2-vinylchromen-4-ylidene)malononitrile

New derivatives of 2-(4-vinylchromen-2-ylidene)malononitrile and 2-(2-vinylchromen-4-ylidene)malononitrile were synthesized using the Knoevenagel reaction of 2-(4-methyl-chromen-2-ylidene)malononitrile and 2-(2-methylchromen-4-ylidene)malononitrile, respectively, with the participation of [1-(2-n-butoxyethyl)-2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinolin-6-yl)]-carbaldehyde. First hyperpolarizability (β) was calculated for the obtained compounds using the M05-2X functional and 6-31+G (d) basis. Optical properties and solvatochromism in solvents of different polarity (toluene, 1,4-dioxane, chlorobenzene, dichloromethane, DMF, and ethanol) were also investigated.

Probing hydrazine with a near-infrared fluorescent chemodosimeter

Hydrazine is highly toxic to humans and animals when inhaled or in contact with the skin. It is also a very important chemical used as propellant, metal corrosion inhibitor, pharmaceutical and intermediate. The simple detection of hydrazine in solution and biosystems becomes very important as a consequence of the foregoing applications. Herein, we report a two-photon fluorescent probing method using a NIR fluorescent chemodosimeter, displaying turn-on fluorescence and color change after cleaving an O-acetyl moiety by hydrazine, which exhibits good selectivity and sensitively in solution and living cells.

A near-infrared fluorescent probe for rapid detection of hydrogen peroxide in living cells

A new near-infrared and colorimetric fluorescent molecular probe was developed for rapid detection of H2O2. The near-infrared fluorescence OFF-ON switch is triggered by transformation of phenylboronic acid unit to phenol in the presence of H2O2. No quinone methides are released in this process, which is preferable for in vivo studies. In addition, probe 1 at low concentration exhibits high quality optical imaging during a short period in in vitro cell study.

An Activatable AIEgen Probe for High-Fidelity Monitoring of Overexpressed Tumor Enzyme Activity and Its Application to Surgical Tumor Excision

Monitoring fluctuations in enzyme overexpression facilitates early tumor detection and excision. An AIEgen probe (DQM-ALP) for the imaging of alkaline phosphatase (ALP) activity was synthesized. The probe consists of a quinoline-malononitrile (QM) core decorated with hydrophilic phosphate groups as ALP-recognition units. The rapid liberation of DQM-OH aggregates in the presence of ALP resulted in aggregation-induced fluorescence. The up-regulation of ALP expression in tumor cells was imaged using DQM-ALP. The probe permeated into 3D cervical and liver tumor spheroids for imaging spatially heterogeneous ALP activity with high spatial resolution on a two-photon microscopy platform, providing the fluorescence-guided recognition of sub-millimeter tumorigenesis. DQM-ALP enabled differentiation between tumor and normal tissue ex vivo and in vivo, suggesting that the probe may serve as a powerful tool to assist surgeons during tumor resection.

A near-infrared fluorescent probe for rapid detection of carbon monoxide in living cells

A near-infrared (NIR) and colorimetric fluorescent probe system was developed for Carbon Monoxide (CO) via a Pd0-mediated Tsuji-Trost reaction. In this probe, phenoxide anion formation (DPCO?) was acted as the signal unit and an allyl carbonate group was used as the recognition unit. This non-fluorescent probe molecule can release the relevant fluorophore after conversion of Pd2+ to Pd0 by CO. The probe system including probe 1 and Pd2+ can be used for “naked-eye” detection of CO, and exhibited high selectivity to CO over various other sensing objects. More importantly, the probe system has great potential for fluorescence imaging of intracellular CO in living cells.

A “turn-on” fluorescent probe with high selectivity and large stokes shift for the detection of hydrogen peroxide and its bioimaging applications

Hydrogen peroxide (H2O2) plays pivotal roles in various biological functions and pharmacological activities. High selectivity and sensitivity remain challenges for fluorescent probes to detection of H2O2 with a large stokes shift. Herein, a new “turn-on” fluorescent probe (DCM-C) was designed based on the mechanism of intramolecular charge transfer (ICT). In PBS buffer (10 mM, pH 7.4, with 20% DMSO, v/v), DCM-C exhibited high selectivity and sensitivity for H2O2 over other interfering analytes with a large stokes shift (187 nm), and the detection limit was as low as 35.5 nM. In addition, the probe was effective for detecting exogenous and endogenous H2O2 in living cells, and identifying stained in cytoplasm. Moreover, the probe has been used successfully for determining H2O2 in zebrafish by fluorescence imaging.

Molecular Aggregation of Naphthalene Diimide(NDI) Derivatives in Electron Transport Layers of Inverted Perovskite Solar Cells and Their Influence on the Device Performance

One of key factors to design applicable electron transport layers (ETLs) for perovskite solar cells is the morphology of ETLs since a good morphology would help to facilitate the carrier transport at two interfaces (perovskiteETL and ETLcathode). However, one drawback of most organic ETL small molecules is the internal undesired accumulation, which would cause the formation of inappropriate morphology and rough ETL surface. Here, by elaborately designing the side chains of NDI derivatives, the molecular interaction could be modified to achieve the aggregation in different degrees, which would eventually affect the accumulation of molecules and surface qualities of ETLs. By speculating from the comparison between the absorption spectra of solutions and films, the sequence of extent of molecule interaction and aggregation was built among three NDI derivatives, which is further confirmed by direct evidence of atomic force microscopy (AFM) images. Then, carrier exaction abilities are simply studied by steady-state photoluminescence spectroscopy. The carrier transport process is also discussed based on cyclic voltammetry, time-resolved photoluminescence spectroscopy and mobility. NDIF1 are proven to have the appropriate internal aggregation to smooth the contact with cathode and low series resistance, and a device performance of 15.6 % is achieved. With the ability of preventing the thermal diffusion of Ag towards the perovskite surface due to the strong interaction between molecules, NDIF2 at high concentration shows the highest fill factor (80 %).

Synthesis and evaluation of styrylpyran fluorophores for noninvasive detection of cerebral β-amyloid deposits

The development of amyloid-specific fluorophores allows the visualization of cerebral β-amyloid deposits using optical imaging technology. In the present study, a series of smart styrylpyran fluorophores with compact donor-acceptor architecture were designed and evaluated for noninvasive detection of cerebral β-amyloid deposits. Spectral behavior of the fluorophores changed significantly (optical turn-on) upon binding to β-amyloid aggregates. Computational studies were conducted to correlate the experimental Kd values with calculated binding energies, speculating the relationship between fluorophore structure and β-amyloid affinity. In vivo studies demonstrated that PAD-2 could discriminate APP/PS1 transgenic mice from wild type controls, with specific labeling of cerebral β-amyloid deposits confirmed by ex vivo observation. Collectively, these styrylpyran fluorophores could provide a new scaffold for the development of optical imaging probes targeting cerebral β-amyloid deposits.