70503-00-3

Upstream product

• 28286-88-6 4-dicyanomethylene-2,6-dimethyl-4H-pyran 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 124-40-3 dimethyl amine 
• 1122-91-4 4-bromo-benzaldehyde 

Relevant academic research and scientific papers

Synthesis method of pyranylidene malononitrile photosensitizer lead compound and application thereof

The invention relates to a synthesis method of the pyranylidene malononitrile photosensitizer lead compound and an application thereof, 2,6-dimethyl-4-pyranylidene malononitrile is taken as a substrate, three micromolecular photosensitizers (PS1-3) with different chain lengths are constructed, the structure is shown as a formula (I), and photodynamic properties and fluorescence properties of the photosensitizers are different. The invention also discloses an application in cell-level tumor imaging and treatment. The lead compound disclosed by the invention has the characteristics of simple structure, small molecular weight, definite chemical structure, easiness in preparation, purification and further modification, low cytotoxicity and the like. The cell experiments prove that near-infrared imaging and photodynamic therapy of cells can be realized by virtue of an external visible light source, and the growth of tumors is remarkably inhibited. Therefore, the monomolecular photosensitizer lead compound provided by the invention has a good application prospect in the aspect of breast cancer treatment.

Transition metal-catalyzed C–N cross-coupling reaction of bromine-substituted pyranilidene derivatives: synthesis, characterization, and optical properties study of pyran-based chromophores

Abstract: In this work, the C–N cross-coupling reaction between bromine-substituted pyranilidene derivatives, and a variety of secondary amines was studied in the presence of transition metal catalysts. The CuI/l-proline, Pd(OAC)2/PPh3, and MnCl2.6H2O/l-proline were chosen as catalyst/ligand systems. The copper-catalyzed Ullmann amination reaction in the presence of l-proline as auxiliary ligand shows the best yield. The structure of pyran-based chromophores was confirmed using FT-IR, 1H NMR, 13C NMR, and mass spectroscopy. Additionally, the linear optical properties of final compounds were investigated using UV–Vis and fluorescent spectroscopy. The large stokes shifts for final compounds show the capability of using these compounds in optical applications. Graphic abstract: [Figure not available: see fulltext.].

Two-photon pumped emission of polymeric thin film doped with dicyanopyranone derivative

Two-photon pumped up-conversion emission of polymeric thin film doped with an organic fluorophore dye (1) is described. It is found that 1 exhibits strong two-photon pumped up-conversion emission in polymeric thin film, and the mechanism shows that the up-conversion emission results from efficient two-photon absorption.

Investigation of 1H NMR chemical shifts of organic dye with hydrogen bonds and ring currents

The 1H NMR chemical shifts were theoretically computed for the organic dyes 2-(2,6-dimethyl-4H-pyran-4-ylidene)-malononitrile (1), cyano-(2,6-dimethyl-4H-pyran-4-ylidene)-acetic acid methyl ester (2), 2-(2,6-bis(4-(dimethylamino)styryl)-4H-pyran-4-ylidene)-malononitrile (3), and methyl 2-(2,6-bis(4-(dimethylamino)styryl)-4H-pyran-4-ylidene)-2-cyanoacetate (4) at the GIAO/B3LYP/6-311++G(d,p)//B3LYP/6-311++G(d,p) level of theory. Moreover, the intramolecular rotational barriers of the molecules were calculated to evaluate the internal flexibility with respect to the torsional degrees of freedom, and the nuclear-independent chemical shifts (NICS) were employed to analyze the ring currents. The difference was explained in terms of intramolecular hydrogen bonds and ring currents of the molecules. The 1H NMR spectra were reproduced by experiments for the comparison with computationally constructed data. Our results suggest a good guideline in interpreting 1H NMR chemical shifts using computational methods and furthermore a reliable perspective for designing molecular structures.