6470-87-7Relevant academic research and scientific papers
Novel Family of Gelators of Organic Fluids and the Structure of Their Gels
Lin, Yih-chyuan,Kachar, Bechara,Weiss, Richard G.
, p. 5542 - 5551 (1989)
The macroscopic and microscopic properties of a new family of thermally reversible gelators (ALS) of organic fluids and their gels have been investigated by a variety of techniques.Each ALS contains a 2-substituted anthracenyl-type group coupled directly or indirectly to C3 of a steroidal group.Only weak intermolecular interactions (dipolar and van der Waals forces) need hold the gelator networks in place.In spite of this, a gel of 2percent cholesteryl 4-(2-anthryloxy)butanoate (CAB) in 4-heptanol can be retained in a sealed vessel at room temperature for several months.Experiments with a variety of organic fluids demonstrate that specific gelator-solvent interactions are not necessary for the gels to form.Thus, n-alkanes from heptane to hexadecane afford the same gelation temperature (Tg) with CAB.Molecular shape of fluid is an important factor in Tg since methylcyclohexane is gelled by CAB at a lower temperature than are the n-alkanes, and 4-heptanol is gelled at a higher temperature.The kinetics of gel formation and the Tg have been followed by changes in intensities of absorption, fluorescence, and circular dichroism spectra.The intermolecular packing arrangement among neighboring CAB gelator molecules has been probed by using the above spectral techniques in addition to X-ray diffraction and (1)H NMR studies.They indicate a stacked, helical arrangement for CAB molecules with the anthracenyl groups overlapping partially.Optical and electron microscopies have allowed the gelator structure in CAB/1-octanol and CAB/dodecane gels to be elucidated: they consist of molecular domains (several micrometers in diameter) of fibrous bundles; the fibers have rectangular cross sections of 20.9 nm X 10.4 nm (dodecane gel) and 25.3 nm X 8.2 nm (1-octanol gel).Additionally, the fibers of the CAB/1-octanol gel are helically twisted.These results are compared with information from other gel systems in which the gelator forms intertwined fibers.
Photoinduced charge transfer between tetracyano-anthraquino-dimethane derivatives and conjugated polymers for photovoltaics
Zerza, Gerald,Scharber, Markus C.,Brabec, Christroph J.,Sariciftci, N. Serdar,Goemez, Rafael,Segura, Jose L.,Martin, Nazario,Srdanov, Vojislav I.
, p. 8315 - 8322 (2000)
The photoinduced charge transfer between tetracyano-anthraquino-dimethane (TCAQ) derivatives and poly[2-methoxy-5-(3,7-dimethyloctyloxy)-1,4-phenylenevinylene] (MDMO-PPV) has been studied by photoinduced absorption (PIA) spectroscopy in the VIS and IR spectral region and by light induced electron spin resonance (LESR). Studies on three different TCAQ derivatives with different side chain substitutions are reported. Among them a supermolecule with TCAQ attached to a fullerene have been synthesized to serve as tandem electron acceptor. The photoinduced absorption in the Vis/near-IR range shows a broad plateau around 1.8 eV followed by two peaks at 1.35 and 1.24 eV with an additional broad feature below 0.5 eV for all three acceptors in composite with MDMO-PPV. All PIA features have a power law excitation intensity dependence with an exponent close to 0.5 as expected for bimolecular kinetics. LESR studies show one absorption at a g-factor of 2.0028 with a width (peak-to-peak) of 3.5 G, originating from TCAQ anion radical and the polymer cation radical. Evidence for the formation of a C60 anion was found in the case of electron transfer from the MDMO-PPV polymer to the TCAQ-C60 acceptor dyade from these LESR studies. Finally bulk-heterojunction type thin film structures of MDMO-PPV as donor and the TCAQ derivatives as acceptor have been fabricated and tested as photovoltaic devices.
Electrochemically driven host-guest interactions on patterned donor/acceptor self-assembled monolayers
Maglione, Maria Serena,Casado-Montenegro, Javier,Fritz, Eva-Corinna,Crivillers, Núria,Ravoo, Bart Jan,Rovira, Concepció,Mas-Torrent, Marta
, p. 3038 - 3041 (2018)
Here, on ITO//Au patterned substrates SAMs of ferrocene (Fc) on the Au regions and of anthraquinone (AQ) on the ITO areas are prepared, exhibiting three stable redox states. Furthermore, by selectively oxidizing or reducing the Fc or AQ units, respectively, the surface properties are locally modified. As a proof-of-concept, such a confinement of the properties is exploited to locally form host-guest complexes with β-cyclodextrin on specific surface regions depending on the applied voltage.
Cross-dehydrogenative Coupling of N-Aryl Tetrahydroisoquinolines Catalyzed by an Anthraquinone-containing Polymeric Photosensitizer
Wang, Fei,Yu, Dan,Chen, Yang,Sun, Jing,Wang, Jing-Yun,Zhou, Ming-Dong
, p. 4087 - 4094 (2021/11/09)
This work reports the photocatalytic application of an anthraquinone-containing polymeric photosensitizer (AQ-PHEMA) in the visible light-induced cross-dehydrogenative-coupling of N-aryl tetrahydroisoquinolines with several nucleophiles, including nitromethane, 1-methyl-2-alkyl ketone and dialkyl (aryl) phosphine oxide. The results revealed that the reaction could be catalyzed by AQ-PHEMA efficiently to afford a series of 1-substituted-2-aryl-1,2,3,4-tetrahydroisoquinolines in good to excellent yields with nice substrate tolerance under aerobic conditions at room temperature. The practical application potential was also showcased by a gram-scale synthesis. More importantly, the utilization of AQ-PHEMA as a heterogeneous photosensitizer also showed nice recyclability and reusability of the catalyst, whereas AQ-PHEMA can be easily separated and reused for at least 8 times without significant loss of photocatalytic activity.
Design, synthesis, and molecular docking studies of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives as xanthine oxidase inhibitors
Zhang, Ting-Jian,Li, Song-Ye,Yuan, Wei-Yan,Zhang, Yi,Meng, Fan-Hao
, p. 893 - 901 (2018/03/21)
A series of N-(9,10-anthraquinone-2-carbonyl)amino acid derivatives (1a–j) was designed and synthesized as novel xanthine oxidase inhibitors. Among them, the L/D-phenylalanine derivatives (1d and 1i) and the L/D-tryptophan derivatives (1e and 1j) were effective with micromolar level potency. In particular, the L-phenylalanine derivative 1d (IC50?=?3.0?μm) and the D-phenylalanine derivative 1i (IC50?=?2.9?μm) presented the highest potency and were both more potent than the positive control allopurinol (IC50?=?8.1?μm). Preliminary SAR analysis pointed that an aromatic amino acid fragment, for example, phenylalanine or tryptophan, was essential for the inhibition; the D-amino acid derivative presented equal or greater potency compared to its L-enantiomer; and the 9,10-anthraquinone moiety was welcome for the inhibition. Molecular simulations provided rational binding models for compounds 1d and 1i in the xanthine oxidase active pocket. As a result, compounds 1d and 1i could be promising lead compounds for further investigation.
Palladium-Catalyzed Decarbonylative Difluoromethylation of Acid Chlorides at Room Temperature
Pan, Fei,Boursalian, Gregory B.,Ritter, Tobias
supporting information, p. 16871 - 16876 (2018/11/23)
Methods for the direct synthesis of difluoromethylated arenes are sparse, despite the importance of the difluoromethyl group in medical, agro-, and materials chemistry. A palladium-catalyzed decarbonylative cross-coupling reaction of acid chlorides with a difluoromethyl zinc reagent is achieved to access difluoromethylated compounds. The transformation proceeds at room temperature and shows broad functional group tolerance, thus providing a general and efficient method for decarbonylative difluoromethylation of a wide range of aromatic carboxylic acids.
2 - substituted - 9, 10 - anthraquinone compound, preparation method and use thereof
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, (2017/08/15)
The invention belongs to the technical field of medicine, and particularly relates to 2-substituted-9,10-anthraquinone compounds represented by the general formula I, the general formula II, the general formula III and the general formula IV, and pharmaceutically acceptable salts, hydrates or solvates and pharmaceutically acceptable carriers thereof. A preparation method comprises the steps: with phthalic anhydride as a starting material, carrying out a Friedel-Crafts reaction, concentrated sulfuric acid dehydration, NBS bromization and sodium azide substitution, generating a key intermediate 2-azide methyl-9,10-anthraquinone, and finally in the presence of copper sulfate pentahydrate and vitamin C, carrying out a Husigen cycloaddition reaction with substituted alkyne; or carrying out concentrated sulfuric acid dehydration, cyclization, chromium trioxide oxidation and thionyl chloride chlorination, to obtain anthraquinone-2-formyl chloride, then carrying out an acylation reaction with various L-amino acid methyl esters, further hydrolyzing, and thus obtaining the target compounds. The prepared compounds show good results in in-vitro antitumor activity tests.
Analyte sensor
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Page/Page column 24; 25, (2016/09/13)
Matrix materials, such as sol-gels and polymers derivatives to contain a redox active material can be used to form electrodes and probes suitable for use in pH meters and other analyte sensing devices.
Tuning reductive and oxidative photoinduced electron transfer in amide-linked anthraquinone-porphyrin-ferrocene architectures
Melomedov, Jascha,Ochsmann, Julian Robert,Meister, Michael,Laquai, Frédéric,Heinze, Katja
supporting information, p. 1984 - 2001 (2015/04/27)
Porphyrin amino acids 3a-3h with meso substituents Ar of tunable electron-donating power (Ar = 4-C6H4OnBu, 4-C6H4OMe, 4-C6H4Me, Mes, C6H5, 4-C6H4F, 4-C6H4CF3, C6F5) have been linked at the N terminus to anthraquinone Q as electron acceptor through amide bonds to give Q-PAr dyads 4a-4h. These were conjugated to ferrocene Fc at the C terminus as electron donor to give the acceptor-chromophore-donor Q-PAr-Fc triads 6a-6h. To further modify the energies of the electronically excited and charge-separated states, the triads 6a-6h were metallated with zinc(II) to give the corresponding Q-(Zn)PAr-Fc triads Zn-6a-Zn-6h. The Q-PAr1 dyad (Ar1 = C6H5) was further extended with a second porphyrin PAr2 (Ar2 = 4-C6H4Me) as well as appended to a ferrocene to give the tetrad Q-PAr1-PAr2-Fc 9. Almost all the conjugates show strongly reduced fluorescence quantum yields and excited-state lifetimes, which has been interpreted as photoinduced electron transfer (PET) either from the excited porphyrin to the quinone (oxidative PET) or from the ferrocene to the excited porphyrin (reductive PET). Electrochemical data, absorption spectroscopy, steady-state emission, time-resolved fluorescence, transient absorption pump-probe spectroscopy as well as DFT calculations have been used to elaborate the preferred PET pathway (reductive vs. oxidative PET) in these architectures with systematically varied electron-donating substituents at the central chromophore. The initial photoinduced electron transfer (PET) in anthraquinone-(porphyrinAr)n-ferrocenes (n = 1, 2) is modulated by the HOMO and LUMO levels of the porphyrin chromophores by meso substituent effects. Electrochemical and spectroscopic data as well as DFT calculations were used to elaborate the preferred PET pathway in these architectures with different electron donation on the porphyrin.
Hybrid functional mesostructured thin films with photo-oxidative properties in the visible range
Saint-Cricq, Philippe,Pigot, Thierry,Nicole, Lionel,Sanchez, Clement,Lacombe, Sylvie
supporting information; experimental part, p. 5281 - 5283 (2010/01/31)
Hybrid mesostructured thin films functionalised with organic photosensitiser molecules demonstrated high efficiency for the decontamination of polluted atmosphere via singlet oxygen production.
