22304-67-2

Upstream product

• 28006-86-2 3,5-dibromo-2,6-dimethoxytoluene 
• 608-25-3 2-methylbenzene-1,3-diol 
• 76-05-1 trifluoroacetic acid 
• 3473-63-0 formamidine acetic acid 
• 100-97-0 hexamethylenetetramine 
• 5673-07-4 2,6-dimethoxytoluene 
• 22304-74-1 4,6-dimethoxy-5-methyl-1,3-benzenedicarbaldehyde 

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• 1427388-11-1 C₂₁H₁₈N₆O₄ 

Relevant academic research and scientific papers

Photo- and thermochromic spirans 37.*New symmetrical bisspiropyrans of the indoline series

New symmetrical bisspiropyrans of the indoline series, which have photochromic properties and are characterized by substantially higher absorption capacity of cyclic isomers in comparison to the monospiropyrans, were obtained on the basis of 4,6-dihydroxy

Novel lysosome-targeted fluorescent molecular rotors based on a cyanine-like modular system and their application in living cells

Two novel fluorescence molecular rotors DpIn and NaIn were designed and synthesized involving of indolium units linked with meta-diphenol or ortha-naphthalenediol moiety, respectively. They underwent intramolecular charge transfer to form a cyanine-like modular system at a physiological pH. In glycerol aqueous solutions, the probe DpIn exhibited NIR strong emission (3-fold) at ca. 700 nm, while the probe NaIn displayed a turn-on emission (8-fold) with a larger Stokes shift (⊿λ ≈ 97 nm). The HeLa cell imaging experiments indicated probe DpIn and NaIn both exhibited excellent selectivity for staining intracellular lysosomes instead of mitochondria. 1H NMR spectra revealed that more electrons were accumulated around benzene ring of indolium groups, which could be the evidence for its basic character leading to the lysosomes targeted staining. Furthermore, the probe NaIn proved to be an ideal lysosome-targeting tracer for monitor the changes of viscosity caused by stimuli in living cells.

Structure-Activity Relationship Studies of Coumarin-like Diacid Derivatives as Human G Protein-Coupled Receptor-35 (hGPR35) Agonists and a Consequent New Design Principle

A series of coumarin-like diacid derivatives were designed and synthesized as novel agonists of human G-protein-coupled receptor 35 (hGPR35). Active compounds were characterized to possess one acidic group on both sides of a fused tricyclic aromatic scaff

A deep-red fluorescent molecular rotor based on donor-two-acceptor modular system for imaging mitochondrial viscosity

A new donor-two-acceptor modular fluorescence rotor DpCy7 involving a phenolate donor unit and two benzothiazolium acceptor moieties was designed and synthesized. The DpCy7 underwent an internal charge transfer to form a Cy7-like longer conjugated system fluorochrome at a physiological pH. The probe exhibited a strong turn-on (8.5-fold) deep-red emission with a larger Stokes shift in glycerol aqueous solutions with restriction of rotation. Both the fluorescence intensity and fluorescence lifetime displayed the linear relationship of viscosity changes in the logarithmic plots. Furthermore, the HeLa cell imaging experiments of DpCy7 indicated that the rotor could be used to monitor the mitochondrial viscosity in living cells. This new type of deep-red fluorescence rotor provides a potential platform for determining viscosity at subcellular levels.

Near infrared emission cyanine fluorescent dye capable of being used for detecting physiological viscosity and preparation method thereof

Near infrared emission cyanine fluorescent dye capable of being used for detecting physiological viscosity and a preparation method thereof are disclosed. The near infrared emission cyanine fluorescent dye is synthesized by changing a methine chain design in a structure of classical cyanine dye, and a synthesis method is safe and simple. In a pure water system, Stokes displacement exceeds 90 nm, the shortcoming that the Stokes displacement of traditional cyanine dye results in self-quenching is greatly improved, and the maximum emission wavelength (670 nm) is located in a near-infrared regionand is suitable for cell imaging. The fluorescence intensity of the dye is significantly enhanced with increasing viscosity, and the dye has high selectivity and sensitivity to viscosity. In cell imaging experiments, the dye exhibits better water solubility, biocompatibility, and less biotoxicity, can perform targeting positioning on subcellular organelle mitochondria, and detects changes of the viscosity in the mitochondria. In summary, the invention provides a design and synthesis method for novel near-infrared emission cyanine dye which can be used for detecting the physiological viscosity.

One-step Access to Resorcinsalens—Solvent-Dependent Synthesis, Tautomerism, Self-sorting and Supramolecular Architectures of Chiral Polyimine Analogues of Resorcinarene

Substituted 2,4- and 4,6-dihydroxyisophthalaldehydes were condensed with optically pure and racemic trans-1,2-diaminocyclohexane to form resorcinarene-like polyimine macrocycles (resorcinsalens), the structure and stoichiometry of which were controlled by the choice of the reaction medium. Particularly, the cyclocondensation reactions were driven by the solubility, tautomerization, or by social self-sorting. The resorcinsalens crystallized as inclusion compounds, in which the guest molecules were situated either in channels or in voids. In the highly hydrated crystals of one of the [2+2] macrocycles and chloroform-solvated crystals of a [4+4] product the channels were interconnected, as in zeolites, enabling possible migration of loosely bound solvent molecules in three dimensions. The association mode depended on the structural modification of the host molecule and the type of included solvent molecule(s).

Formylation of phenols using formamidine acetate

We report a new method to formylate phenol derivatives using formamidine acetate and acetic anhydride. This general-purpose transformation is a significant improvement over many other methods and does not require high temperatures or the addition of strong acid or base. Mono-, di-, and tri-formylated product can be obtained, depending on the substrate and conditions used.

Supramolecular lanthanide metallogrids exhibiting field-induced single-ion magnetic behavior

A supramolecular strategy has been applied to construct two tetranuclear lanthanide complexes for investigating the magnetic properties of individual lanthanide ions. The LnIII complexes (Ln = Dy, Tb) display field-induced slow magnetization relaxation, typical of single-molecule magnet behavior. The four lanthanide ions in the molecules are well separated by distances of ca. 9 A, and thus the slow magnetization relaxation should be assigned to single-ion magnet (SIM) behavior. Therefore, the present complexes are novel supramolecular aggregates of four isolated SIMs. The Royal Society of Chemistry 2013.

General and efficient protocol for formylation of aromatic and heterocyclic phenols

A convenient, general procedure for formylation of diverse range of phenols with the Duff protocol has been developed. The procedure gives dialdehydes when possible. Georg Thieme Verlag KG Stuttgart · New York.

Conjugated macrocycles related to the porphyrins. Part 18: Synthesis and spectroscopic characterization of electron-rich benzi- and oxybenziporphyrins: Influence of steric and electronic factors on porphyrinoid aromaticity

Although 4,6-dihydroxyisophthalaldehydes failed to condense with tripyrranes to produce porphyrinoid products, the related dimethoxydialdehydes reacted with tripyrrane 9 to give, following oxidation with aqueous ferric chloride solution, nonaromatic dimet