- Control of the aggregation of a phenylenevinylenediimide chromophore by use of supramolecular chemistry: Enhanced electroluminescence in supramolecular organic devices
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A new approach toward the tuning of the supramolecular organization of π-conjugated substructures containing imide functional groups has been investigated using the concept of supramolecular chemistry. This approach, which allows enhanced emission properties of the active material, was evaluated in the fabrication of optoelectronic devices. A linear ditopic chromophore H-ImPV was synthesized. This N-H imide constitutes a recognizing unit with an acceptor-donor-acceptor (ADA) hydrogen bond motif. End-capping of this new chromophore with a monotopic structuring unit allowed control of the supramolecular aggregation of the π-conjugated chromophore. The studies of the absorption and emission properties of the H-ImPV, in solution or in the solid state (thin films, powders), clearly revealed different aggregation behaviors, depending on the presence of the monotopic structuring unit: hindered unit (Cy-DAT) led to the formation of J-aggregates. In all cases, evidence for the heteromolecular association H-ImPV...Cy-DAT was obtained from an infrared absorption band located at 2715 cm-1, which was typical of the hydrogen bonding present in the ADA...DAD triplet. This has been illustrated by the fabrication of light-emitting devices based on films of H-ImPV and [H-ImPV.(Cy-DAT)2]. H-ImPV presents a poor ability to emit light, because of its aggregation, which induces quenching of luminescence. The high efficiencies exhibited by the devices based on a single layer of [H-ImPV.(Cy-DAT)2] are the result of the J-aggregation of chromophores, because of the bulky cyclohexyl fragments of the Cy-DAT. Tuning of the supramolecular organization of the H-ImPV by the addition of two equivalents of Cy-DAT in the active layer allowed recovery of the performances exhibited by the organic light-emitting devices (OLEDs) of the isolated chromophore. Therefore, the use of Cy-DAT is an interesting alternative to avoid aggregation and to significantly increase luminance. As a consequence, the luminous efficiencies of the devices are much better for the coassembled active layer.
- Delbosc, Nicolas,Reynes, Mathias,Dautel, Olivier J.,Wantz, Guillaume,Lere-Porte, Jean-Pierre,Moreau, Joel J. E.
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- 2,4,6-trisubstituted-1,3,5-s-triazine compound and preparation and application thereof
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The invention provides a 2,4,6-trisubstituted-1,3,5-s-triazine compound as well as preparation and application thereof, and biguanide or dimethyl biguanide hydrochloride is used as an initial raw material to react with a cyano compound under an alkaline condition to prepare the 2,4,6-trisubstituted-1,3,5-s-triazine compound. The invention provides a simple and convenient synthetic method of a 2,4,6-trisubstituted-1,3,5-s-triazine compound, and the compound provided by the invention can be applied to preparation of an anti-myelogenous leukemia medicine, namely an enasidenib medicine. Compared with the prior art, the method for preparing the enasidenib has the advantages that two-step reaction is reduced, the use of a halogenating reagent is avoided, and the method is a green and environment-friendly chemical process. The structural formula I is shown in the specification.
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Paragraph 0028; 0056
(2021/10/05)
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- Synthesis, molecular docking studies, and in vitro evaluation of 1,3,5-triazine derivatives as promising antimicrobial agents
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The six-membered ring heterocycle 1,3,5-triazine and its derivatives have attracted considerable attention as they have proven to be excellent bioactive herbicides, cancer agents, etc. A series of 1,3,5-triazine derivatives (3a-o) were synthesized by a single step reaction and characterized by 1H NMR, 13C NMR, and mass spectrometry analysis. Antimicrobial screening of title compounds (3a-o) was examined against five bacterial and two fungal strains. In vitro study revealed that the freshly synthesized 6-(thiazol-4-yl)-1,3,5-triazine-2,4-diamine (3o) showed good antibacterial growth inhibition against E. coli, K. pneumoniae, and A. baumannii bacterial strains, and even the fungi C. neoformans. Molecular docking studies were performed on the X-ray crystal structure of E. coli 24 kDa domain in complex with clorobiocin (PDB code: 1KZN; resolution 2.30 ?) using Surflex-Dock program of Sybyl-X software. The results obtained are very encouraging.
- Bugarin, Alejandro,Joshi, Shrinivas D.,Lewis, Abby M.,Noonikara-Poyil, Anurag,Patil, Shivaputra A.,Patil, Siddappa A.,Patil, Vikrant
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- Novel benzoguanamine production method
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The invention discloses a novel benzoguanamine production method. The method comprises the following steps that 1, a certain amount of alkanol is added into a reaction vessel to serve as a solvent, benzonitrile and dicyandiamide are added, and on the condition that an inorganic base serves as a catalyst, a complete reaction is conducted; 2, reactant is cooled to be below 40 DEG C, suction filtration is conducted, and solid-liquid separation is achieved; 3, all solid substances obtained through suction filtration are transferred into the vessel, pure water of which the volume is 1-3 times that of the solid substances is added, heating and constant-temperature evaporation are conduced for 1 h to 3 h, and suction filtration is conducted when the solid substances are hot; 4, solid substances obtained through suction filtration in the third step are added into hot water of which the volume is 1-3 times that of the obtained solid substances to be washed with water for 10 min to 30 min, and suction filtration is conducted again to obtain solid substances; 5, the solid substances obtained through suction filtration in the fourth step are dried and crushed, and the competitive benzoguanamine product is obtained. According to the production method, the conversion rate of the production raw materials is high, the purity of the obtained product is high, unreacted raw materials in the benzoguanamine production process can be effectively recycled, and therefore types and COD of organic matter in wastewater after reaction are obviously reduced.
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Paragraph 0018; 0019; 0020; 0021; 0022; 0023; 0024-0049
(2017/05/12)
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- Hydrogen-bonded arrays coupled by cross-metathesis
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Recently, supramolecular assemblies have been created as responsive, reversible, and dynamic materials. By a modular approach, we discuss the reversible cross-metathesis of terminal olefins containing self-complementary hydrogen-bond donor and acceptor arrays. These compounds are readily constructed from 2,6-diaminotriazines or cytosine and chiral elements can be installed from modified amino acids. Dynamic combinatorial libraries should be accessible via this approach. Georg Thieme Verlag Stuttgart.
- Enholm, Eric J.,Hastings, Jed M.,Edwards, Chris
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p. 203 - 206
(2008/09/21)
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- Microwave-assisted one-pot tandem reactions for direct conversion of primary alcohols and aldehydes to triazines and tetrazoles in aqueous media
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(Chemical Equation Presented) A series of primary alcohols and aldehydes were treated with iodine in ammonia water under microwave irradiation to give the intermediate nitriles, which without isolation underwent [2 + 3] cycloadditions with dicyandiamide and sodium azide to afford high yields of the corresponding triazines and tetrazoles, including the α-amino- and dipeptidyl tetrazoles in high optical purity.
- Shie, Jiun-Jie,Fang, Jim-Min
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p. 3141 - 3144
(2008/02/13)
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- Green synthesis and self-association of 2,4-diamino-1,3,5-triazine derivatives
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2,4-Diamino-1,3,5-triazines have been prepared by reaction of dicyandiamide with nitriles under microwave irradiation, a method that can be considered as a green procedure due to the reduction in the use of solvents during synthesis and purification, the short reaction time and the simplicity of the procedure. The structures have been confirmed in solution by NMR spectroscopy. Variable temperature experiments have been used to calculate the free energy of activation for rotation about the amino-triazine bond. The crystal structures of three 2,4-diamino-6-R-1,3,5-triazine derivatives (3a: R = phenyl, 3i: R = 1-piperidino and 3g: R = 1-phenylpyrazol-3-yl) have been determined by X-ray analysis. The N-H...N interactions change from structure to structure, resulting in a variation from pseudo-honeycomb networks to corrugated rosette layers.
- Diaz-Ortiz, Angel,Elguero, Jose,Foces-Foces, Concepcion,De La Hoz, Antonio,Moreno, Andres,Del Carmen Mateo, Maria,Sanchez-Migallon, Ana,Valiente, Gema
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p. 952 - 958
(2007/10/03)
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- Microwave-assisted clean synthesis of 6-aryl-2,4-diamino-1,3,5-triazines in [bmim][PF6]
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An efficient and green approach was developed to prepare 6-aryl-2,4-diamino-1,3,5-triazines from corresponding arylnitriles and dicyanodiamide in ionic liquid [bmim][PF6] under computer-controlled microwave irradiation. Particularly valuable features of this method included the short reaction time, good yield, convenient operation and eco-friendly solvent.
- Peng, Yanqing,Song, Gonghua
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p. 5313 - 5316
(2007/10/03)
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- Direct conversion of aldehydes to amides, tetrazoles, and triazines in aqueous media by one-pot tandem reactions
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A variety of aldehydes reacted with iodine in ammonia water at room temperature to give the nitrile intermediates, which were trapped by addition of hydrogen peroxide, sodium azide, or dicyandiamide to produce their corresponding amides, tetrazoles, and 1,3,5-triazines in modest to high yields. The one-pot tandem reactions were conducted in water media, and the products were obtained simply by extraction or filtration.
- Shie, Jiun-Jie,Fang, Jim-Min
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p. 1158 - 1160
(2007/10/03)
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- Synthesis of 6-aryl-2,4-diamino-pyrimidines and triazines using palladium catalysed Suzuki cross-coupling reactions
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The high yielding synthesis of 6-aryl-2,4-diaminopyrimidines and triazines via palladium catalysed Suzuki cross-coupling reactions of commercially available 6-chloro-2,4-diaminopyrimidine 1 or 6-chloro-2,4-diaminotriazine 8 and aryl boronic acids are desc
- Cooke,Augier de Cremiers,Rotello,Tarbit,Vanderstraeten
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p. 2787 - 2789
(2007/10/03)
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- Colorant compositions and processes
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A process for making solid colored particles by preparing a reaction solution in water comprising formaldehyde, urea, a cyclic polyamine functional triazine compound, and acid. A dye can be incorporated into the reaction solution if a color other than white is desired. Particles are formed having an average particle size between 1 and 70 microns without the need to resort to crushing to break up agglomerates. Particles made by this process provide excellent color and are easily washable from a substrate when incorporated into a washable formulation. Additionally, it has been found that the incorporation of colored microcapsules of average size of 1-70 microns where the color is located primarily on or in the shell of the microcapsule also provides excellent washable compositions when incorporated into a washable formulation.
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- Model Systems for Flavoenzyme Activity. Regulation of Flavin Recognition via Modulation of Receptor Hydrogen-Bond Donor-Acceptor Properties
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We have synthesized a new family of receptors for flavins based on 6-aryl-2,4-(acyldiamino)-s-triazines. In these synthetic hosts, systematic variation of the spatially remote substituents on the 6-aryl ring alters the hydrogen-bond-donating abilities of the amide functionality and the hydrogen-bond-accepting properties of the triazine N(3). This variation results in a strong modulation of the efficiency of flavin binding, with association constants for the receptor flavin complexes ranging over an 8-fold range.
- Deans, Robert,Cooke, Graeme,Rotello, Vincent M.
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p. 836 - 839
(2007/10/03)
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- ANTICANCER COMPOSITION AND COMPOUND
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An anticancer composition containing a compound represented by general formula (I) or a pharmacologically acceptable acid addition salt thereof. In formula (I), R10 and R20 may be the same or different from each other and each represents hydrogen, halogen, amino, aralkylamino, nitro, lower alkyl, lower alkoxy, lower alkoxyalkoxy, lower aralkyloxy or acyl; R30 and R40 may be the same or different from each other and each represents hydrogen, nicotinoyl, benzoyl or lower alkoxy; and n represents 0 or 1.
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- A potassium amide induced ring transformation of 1,2,4-triazines into 1,2,4-triazoles and 1,3,5-triazines
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5-Phenyl- and 3,5-diphenyl-1,2,4-triazine, when treated with potassium amide in liquid ammonia, are converted into a mixture of phenyl derivatives of 1,2,4-triazole and amino-1,3,5-triazines. The ring contraction of the 1,2,4-triazine ring into the 1,2,4-triazole ring has been explained by an initial addition of the amide ion to C-6, ring opening by fission of the N1-C6 bond and ring closure (ANRORC-mechanism). The transformation of the 1,2,4-triazine ring into the 1,3,5-triazine ring has been studied by means of 15N-labeled potassium amide. It was found that the nitrogen of the amide ion becomes one of the ring nitrogen atoms in the 1,3,5-triazine ring and that the exocyclic amino group is imlabeled. Based on these 15N-labeling studies, it is proposed that this ring transformation starts with an initial addition of the amide ion to C-5, ring opening between C-5 and C-6, a dehydrogenative rearrangement of the open-chain intermediate 1-amino-2,4,5-triazahexatriene into 1-amino-4-cyano-2,4-diaza-1,3-butadiene, and ring closure.
- Rykowski,Van Der Plas
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- Hydroxide-Catalyzed Synthesis of Heterocyclic Aromatic Amine Derivatives from Nitriles
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A generalized method for synthesizing a wide variety of heterocyclic aromatic amine derivatives from nitriles by use of hydroxide catalysts is presented.Nitrile dimers (3-aminocrotononitrile and dicyandiamide) and a dimer analog (anthranilonitrile) react with monomeric nitriles in the presence of hydroxide to form respectively, aminopyrimidines, diaminotriazines and aminoquinazolines.
- Smyrl, Norman R.,Smithwick, Robert W.
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p. 493 - 496
(2007/10/02)
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