22245-51-8

Usage

Uses

Used in Biochemical Applications:
Pyrene-4-carbaldehyde is used as a fluorescent probe for various biochemical applications, such as studying protein-protein interactions, monitoring enzyme activity, and detecting specific biomolecules. Its fluorescent properties allow for sensitive and selective detection of target molecules, making it a valuable tool in research and diagnostics.
Used in Environmental Applications:
In environmental science, Pyrene-4-carbaldehyde serves as a fluorescent probe for monitoring and analyzing environmental samples. It can be used to detect the presence of pollutants, assess water quality, and study the behavior of contaminants in the environment.
Used in Organic Solar Cells:
Pyrene-4-carbaldehyde is used as a photosensitizer in the development of organic solar cells. Its ability to absorb light and generate excited states makes it a promising candidate for improving the efficiency and performance of solar cell devices.
Used in Synthesis of Heterocyclic Compounds:
Pyrene-4-carbaldehyde is utilized as a precursor in the synthesis of heterocyclic compounds, which are important building blocks in the pharmaceutical and chemical industries. Its unique structure and reactivity contribute to the formation of diverse and complex molecular architectures.
Used in Chemical Research:
Pyrene-4-carbaldehyde is employed in chemical research to study the properties and reactions of polycyclic aromatic hydrocarbons. Its use in various chemical transformations and reactions helps to advance the understanding of PAH chemistry and its potential applications in materials science and other fields.

InChI:InChI=1/C17H10O/c18-10-14-9-13-5-1-3-11-7-8-12-4-2-6-15(14)17(12)16(11)13/h1-10H

Upstream product

• 129-00-0 pyrene 
• 4885-02-3 Dichloromethyl methyl ether 
• 24295-83-8 1-Formyl-3,4,5,8,9,10-hexahydro-pyran 
• 1732-13-4 1,2,3,6,7,8-hexahydropyrene 
• 22245-54-1 4-hydroxymethylpyrene 
• 1732-26-9 4-bromopyrene 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 73529-24-5 4-oxiranylpyrene 
• 957-38-0 1-(chloromethyl)pyrene 
• 129-00-0 pyrene 

Relevant academic research and scientific papers

Efficient oxidation of promutagenic hydroxymethylpyrenes by cDNA-expressed human alcohol dehydrogenase ADH2 and its inhibition by various agents

Alkylated polycyclic aromatic hydrocarbons can be metabolically activated via benzylic hydroxylation and sulphation to electrophilically reactive esters. However, we previously found that the predominant biotransformation route for the hepatocarcinogen 1-hydroxymethylpyrene (1-HMP) in the rat in vivo is the oxidation of the side chain by alcohol dehydrogenases (ADHs) and aldehyde dehydrogenases to the carboxylic acid. Inhibition of this pathway by ethanol (competing ADH substrate) or 4-methylpyrazole (ADH inhibitor) led to a dramatic increase in the 1-HMP-induced DNA adduct formation in rat tissues in the preceding study. In order to elucidate the role of individual ADHs in the metabolism of alkylated polycyclic aromatic hydrocarbons, we expressed the various members of the human ADH family in bacteria. Cytosolic preparations from bacteria expressing ADH2 clearly oxidized hydroxymethylpyrene isomers (1-, 2- and 4-HMP) with the highest rate. This form was purified to near homogeneity to perform detailed kinetic analyses. High catalytic efficiencies (Vmax/Km) were observed with HMPs. Thus, this value was 10,000-fold higher for 2-HMP than for the reference substrate, ethanol. The corresponding aldehydes were also efficiently reduced by ADH2. 4-Methylpyrazole inhibited the oxidation of the HMP isomers as well as the reverse reaction. Daidzein, cimetidine and the competing substrate ethanol were further compounds that inhibited the ADH2-mediated oxidative detoxification of 1-HMP.

Synthesis method of high-purity 1-pyrenecarboxaldehyde

The invention discloses a synthesis method of high-purity 1-pyrenecarboxaldehyde. The synthesis method is characterized in that pyrene is fed into an organic solvent; stirring is performed for dissolution; dichloromethyl methyl ether is injected and added into reaction liquid; the reaction liquid is cooled by ice-salt bath; then, a mixed solution of TiCI4 and dichloromethane is dropwise added; the reaction liquid is subjected to quenching reaction; after the quenching is completed, water is added; stirring is performed for layering; an organic phase is subjected to working procedures such as washing and drying; a crude product 1-pyrenecarboxaldehyde is obtained; the crude product 1-pyrenecarboxaldehyde is subjected to heating and backflow dissolution by organic solvents; active carbon is added for decoloration; through the working procedures of heat filtering, cooling crystallization and the like, the 1-pyrenecarboxaldehyde is obtained; the GC content is 99.5 percent; the total yield of the reaction is 80 percent or higher. The used synthesis raw materials are cheap, can be easily obtained, and are industrial products; the reaction conditions are mild; the risk is low; the operation is convenient; the reaction is easy to control; the synthesis method is suitable for industrial production.

Electronic Structure and Multicatalytic Features of Redox-Active Bis(arylimino)acenaphthene (BIAN)-Derived Ruthenium Complexes

The article examines the newly designed and structurally characterized redox-active BIAN-derived [Ru(trpy)(R-BIAN)Cl]ClO4 ([1a]ClO4-[1c]ClO4), [Ru(trpy)(R-BIAN)(H2O)](ClO4)2 ([3a](ClO4)2-[3c](ClO4)2), and BIAO-derived [Ru(trpy)(BIAO)Cl]ClO4 ([2a]ClO4) (trpy = 2,2′:6′,2′′-terpyridine, R-BIAN = bis(arylimino)acenaphthene (R = H (1a+, 3a2+), 4-OMe (1b+, 3b2+), 4-NO2 (1c+, 3c2+), BIAO = [N-(phenyl)imino]acenapthenone). The experimental (X-ray, 1H NMR, spectroelectrochemistry, EPR) and DFT/TD-DFT calculations of 1an-1cn or 2an collectively establish {RuII-BIAN0} or {RuII-BIAO0} configuration in the native state, metal-based oxidation to {RuIII-BIAN0} or {RuIII-BIAO0}, and successive electron uptake processes by the α-diimine fragment, followed by trpy and naphthalene π-system of BIAN or BIAO, respectively. The impact of the electron-withdrawing NO2 function in the BIAN moiety in 1c+ has been reflected in the five nearby reduction steps within the accessible potential limit of -2 V versus SCE, leading to a fully reduced BIAN4- state in [1c]4-. The aqua derivatives ({RuII-OH2}, 3a2+-3c2+) undergo simultaneous 2e-/2H+ transfer to the corresponding {RuIV-O} state and the catalytic current associated with the RuIV/RuV response probably implies its involvement in the electrocatalytic water oxidation. The aqua derivatives (3a2+-3c2+) are efficient and selective precatalysts in transforming a wide variety of alkenes to corresponding epoxides in the presence of PhI(OAc)2 as an oxidant in CH2Cl2 at 298 K as well as oxidation of primary, secondary, and heterocyclic alcohols with a large substrate scope with H2O2 as the stoichiometric oxidant in CH3CN at 343 K. The involvement of the {RuIV-O} intermediate as the active catalyst in both the oxidation processes has been ascertained via a sequence of experimental evidence.

Recognition of double-stranded DNA using energetically activated duplexes with interstrand zippers of 1-, 2- or 4-pyrenyl-functionalized O2′-alkylated RNA monomers

Despite advances with triplex-forming oligonucleotides, peptide nucleic acids, polyamides and-more recently-engineered proteins, there remains an urgent need for synthetic ligands that enable specific recognition of double-stranded (ds) DNA to accelerate studies aiming at detecting, regulating and modifying genes. Invaders, i.e., energetically activated DNA duplexes with interstrand zipper arrangements of intercalator-functionalized nucleotides, are emerging as an attractive approach toward this goal. Here, we characterize and compare Invaders based on 1-, 2- and 4-pyrenyl-functionalized O2′-alkylated uridine monomers X-Z by means of thermal denaturation experiments, optical spectroscopy, force-field simulations and recognition experiments using DNA hairpins as model targets. We demonstrate that Invaders with +1 interstrand zippers of X or Y monomers efficiently recognize mixed-sequence DNA hairpins with single nucleotide fidelity. Intercalator-mediated unwinding and activation of the double-stranded probe, coupled with extraordinary stabilization of probe-target duplexes (ΔTm/modification up to +14.0 °C), provides the driving force for dsDNA recognition. In contrast, Z-modified Invaders show much lower dsDNA recognition efficiency. Thus, even very conservative changes in the chemical makeup of the intercalator-functionalized nucleotides used to activate Invader duplexes, affects dsDNA-recognition efficiency of the probes, which highlights the importance of systematic structure-property studies. The insight from this study will guide future design of Invaders for applications in molecular biology and nucleic acid diagnostics.

Retro-cycloaddition reaction of pyrrolidinofullerenes

(Chemical Equation Presented) All things retro: Pyrrolidinofullerenes undergo a retro-cycloaddition reaction to afford the corresponding fullerene (C60, C70, or an endohedral C80 metallofullerene; see scheme) in quantitative yield upon treatment with an excess of a dipolarophile (maleic anhydride or N-phenyl-maleimide) in o-dichlorobenzene. The reaction works efficiently with higher fullerenes and has allowed the isolation of one of the constitutional isomers of Sc 3N@C80.

2-[(arylmethyl)amino]-2-methyl-1,3-propanediol DNA intercalators. An examination of the effects of aromatic ring variation on antitumor activity and DNA binding

The effects of variation of aromatic ring size, shape, and side-chain position on antitumor activity and DNA binding in a series of carbocyclic 2-[(arylmethyl)amino]-2-methyl-1,3-propanediols (AMAPs) were examined. In general, the interaction of AMAPs wit