6931-31-3Relevant academic research and scientific papers
Fluorescent phenanthroimidazoles functionalized with heterocyclic spacers: Synthesis, optical chemosensory ability and two-photon absorption (TPA) properties
Ferreira, Rosa Cristina M.,Costa, Susana P. G.,Gon?alves, Hugo,Belsley, Michael,Raposo, Maria Manuela M.
, p. 12866 - 12878 (2017)
Three series of fluorescent phenanthroimidazoles bearing heterocyclic spacers were synthesized in moderate to excellent yields and evaluated as optical chemosensors for ions as well as two-photon absorbing chromophores. Interaction of compounds 5-7 with anions and cations in acetonitrile and acetonitrile/H2O (95:5) showed them to be selective receptors for several anions (AcO-, CN- and F-) and cations (Fe3+, Cu2+ and Pd2+), with compound 7a being the most sensitive receptor for Fe3+ and Cu2+. On the other hand, compounds 5a, 7b and 7c were the most sensitive receptors for AcO-, CN- and F-. The binding stoichiometry between the receptors and the anions and cations was found to be 1:2 (ligand to anion/metal cation). The binding process was also followed by 1H NMR titrations. The evaluation of the TPA properties of chosen phenanthroimidazoles 7a-c by the two-photon induced fluorescence method revealed that compound 7c, which contains a bithienyl spacer, exhibited the highest TPA cross-section (σ2) value.
Phenanthroimidazole derivatives as a chemosensor for picric acid: A first realistic approach
Ahmed, Ruby,Ali, Abid,Ahmad, Musheer,Alsalme, Ali,Khan, Rais Ahmad,Ali, Farman
, p. 20092 - 20100 (2020/12/21)
A series of phenanthroimidazole (PI) derivatives (M1-M3): 2-phenyl-1H-phenanthro [9,10-d]imidazole (M1), 2-anthryl-1H-phenanthro[9,10-d]imidazole (M2), and 2-pyrenyl-1H-phenanthro[9,10-d]imidazole (M3) were synthesized and characterized using various spectroscopic techniques. The fluorescence quenching studies or sensing properties of the molecules M1-M3 with picric acid (PA) were studied. The molecules (M1-M3) exhibit strong fluorescence with a peak emission wavelength at 386, 486 and 456 nm. This emission gets quenched with the addition of PA. The mechanism of fluorescence quenching involves proton transfer from PA to M in the ground state, followed by the formation of a complex between the cation (M+) and picrate anion (PA-). The proton transfer breaks the conjugation inside the imidazole ring which in turn leads to loss of fluorescence. The proof of proton transfer was evident from the single X-ray crystal structure of the co-crystals (M1+-PA- and M3+-PA-) and their Hirshfeld surface analysis. Time-resolved fluorescence measurements reveal that quenching is static. The complex formation constant (Ks) and life-time for all the molecules are measured. This journal is
Synthesis of 5-(4-(1H-phenanthro[9,10-d]imidazol-2-yl)benzylidene)thiazolidine-2,4-dione as promising DNA and serum albumin-binding agents and evaluation of antitumor activity
Singh, Iqubal,Rani, Richa,Luxami, Vijay,Paul, Kamaldeep
, p. 267 - 280 (2019/02/06)
A series of phenanthro[9,10-d]imidazole/oxazole and acenaphtho[1,2-d]imidazole with different aryl groups at C2-position has been synthesized. These compounds were in vitro evaluated for antitumor activity against a panel of 60 human cancer cell lines. Co
Citrate trisulfonic acid: A heterogeneous organocatalyst for the synthesis of highly substituted Imidazoles
Kanaani, Elham,Nasr-Esfahani, Masoud
, p. 119 - 125 (2018/09/11)
Citrate trisulfonic acid (CTSA), as a novel recyclable and eco-benign organocatalyst, was employed for the efficient and one-pot synthesis of trisubstituted imidazoles and tetrasubstituted imidazoles using aldehydes, ammonium acetate or aniline, and benzoin, benzyl, or 9,10-phenanthrenequinone under solvent-free conditions providing high to excellent yields. CTSA is easily prepared via the reaction of trisodium citrate and chlorosulfonic acid in high purity. Compared to the conventional procedures, the present method offers several advantages, including high yields, easy work-up, short reaction time, reusability of the catalyst, and simple purification of the products.
Urea-Zinc Chloride Eutectic Mixture-Mediated One-Pot Synthesis of Imidazoles: Efficient and Ecofriendly Access to Trifenagrel
Higuera, Natalia López,Pe?a-Solórzano, Diana,Ochoa-Puentes, Cristian
supporting information, p. 225 - 229 (2019/01/14)
The low-melting mixture urea-ZnCl 2 was evaluated as a novel reaction medium for the synthesis of imidazoles. The reaction between a dicarbonyl compound, ammonium acetate, and an aromatic aldehyde is efficiently catalyzed by the eutectic solvent, yielding a wide variety of triaryl-1 H -imidazoles or 2-aryl-1 H -phenanthro[9,10- d ]imidazoles in good to excellent yields. In addition, the eutectic solvent was reused in five cycles without loss of its catalytic activity. This protocol was further explored for the synthesis of the drug trifenagrel, giving an excellent yield.
Efficientone-pot synthesis of imidazoles catalyzed by silica-supported La0.5Pb0.5MnO3 nano particles as anovel and reusable perovskite oxide
Zahedi, Najmeh,Javid, Ali,Mohammadi, Mohammad Kazem,Tavakkoli, Haman
, p. 157 - 166 (2018/04/20)
Silica-supported La0.5Pb0.5MnO3 nanoparticles was prepared and used as a new perovskite-type catalyst for rapid and efficient synthesis of substituted imidazoles by an one-pot three-component condensation of [9,10]-phenanthraquinone, aryl aldehydes and ammonium acetate in excellent yield under reflux, and also solvent-free conditions.
Photoenolization via excited state proton transfer and ion sensing studies of hydroxy imidazole derivatives
Shahid, Mohammad,Misra, Arvind
, p. 190 - 199 (2016/12/16)
A light stimulated photo-enolization in hydroxy imidazole systems (o-hydroxynaphthyl phenanthroimidazole, 3 and o-hydroxyphenyl phenanthroimidazole, 4) by excited state proton transfer induces “turn Off” fluorescence and ratiometric changes in the absorption spectrum. Benzyl phenanthroimidazole (5) does not exhibit the photo-enolization due to absence of o-hydroxyl group. Solvatochromism, time resolved photoluminescence measurement and ionic interactions studies of 3–5 are examined in semi-aqueous medium through UV–vis and fluorescence spectroscopy. Fluorescent probe 3 exhibits fluorescence “turn Off” and “turn On” responses with acetate ions in semi-aqueous medium by tuning the excitation wavelength.
Preparation, Characterization, and Application of Preyssler Heteropoly Acid Immobilized on Magnetic Nanoparticles as a Green and Recoverable Catalyst for the Synthesis of Imidazoles
Javid,Khojastehnezhad,Pombeiro
, p. 3000 - 3005 (2018/02/21)
An efficient, magnetically separable catalyst was synthesized by immobilization of Preyssler heteropoly acid (HPA) on Ni0.5Zn0.5Fe2O4 magnetite nanoparticles (MNPs) coated with hydroxyapatite (HA). The catalyst was characterized by scaning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD), FT-IR, energy dispersive spectroscopy (EDS), and TGA. Activity of this catalyst was tested in the synthesis of imidazole derivatives via one-pot three-component condensation of [9,10]-phenanthraquinone with aryl aldehydes and ammonium acetate at room temperature under solvent-free conditions.
Structure-property relationship of blue solid state emissive phenanthroimidazole derivatives
Ivanauskaite, Agne,Lygaitis, Ramunas,Raisys, Steponas,Kazlauskas, Karolis,Kreiza, Gediminas,Volyniuk, Dmytro,Gudeika, Dalius,Jursenas, Saulius,Grazulevicius, Juozas V.
, p. 16737 - 16748 (2017/07/22)
Seven new derivatives of phenanthro[9,10-d]imidazole having differenet substituents at the 1st and the 2nd positions of the phenanthroimidazole moiety were synthesized and characterized. The comparative study of their properties was performed employing thermal, optical, electrochemical and photoelectrical measurements. The properties of the newly synthesized compounds were compared with those of earlier reported derivatives of phenanthroimidazole and several interesting new findings were disclosed. Density functional theory calculations accompanied by optical spectroscopy measurements have shown the possibility of tuning the emission properties (excited-stated decay rate, fluorescence quantum yield, etc.) of phenanthro[9,10-d]imidazole derivatives via attachment of different substituents to the 1st and the 2nd positions. The most polar and bulky substituents linked to the 2nd position were found to have the greatest impact on the emissive properties of compounds causing (i) fluorescence quantum yield enhancement of dilute liquid and solid solutions (up to 97%), (ii) suppression of intramolecular torsion-induced nonradiative excited-state relaxation in rigid polymer films as well as (iii) inhibition of aggregation-promoted emission quenching in the neat films. Most of the studied compunds exhibited ambipolar charge transport character with comparable drift mobilities of holes and electrons. The highest hole and electron mobilities approaching 10-4 cm2 V-1 s-1 were observed for the derivative having a triphenylamino group at the 1st position of the imidazole ring and the phenyl group at the 2nd position. The estimated triplet energies of phenanthro[9,10-d]imidazole compounds were found to be in the range of 2.4-2.6 eV, which is sufficiently high to ensure effective energy transfer to yellow/red emitters.
Method for preparing 2-aryl-1H-phenanthro (9,10-d) imidazole derivative in catalyzed mode
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Paragraph 0020; 0021; 0022, (2016/10/31)
The invention discloses a method for preparing a 2-aryl-1H-phenanthro (9,10-d) imidazole derivative in a catalyzed mode, and belongs to the technical field of ionic liquid catalysis. In a preparation reaction, the molar ratio of 9,10-phenanthrenequinone to aromatic aldehyde to ammonium acetate is 1:1:3-5, the molar weight of a non-imidazolyl acidic ionic liquid catalyst accounts for 4-6% that of 9,10-phenanthrenequinone, the volume dose of reaction solvent water in units of milliliter is 5-8 times the molar weight of 9,10-phenanthrenequinone in units of millimole, the time for a reflux reaction is 14-30 min, diethyl ether is used for extraction after the reaction is finished, anhydrous magnesium sulfate is added into extract liquor for drying, suction filtration is carried out, and after rotary evaporation concentration is carried out, filtrate is recrystallized with ethyl acetate to obtain the 2-aryl-1H-phenanthro (9,10-d) imidazole derivative. The method has the advantages that the catalyst is good in biodegradability and high in raw material use ratio, the whole preparation process is easy and convenient to operate and the like, and the method can be industrially applied on a large scale conveniently.
