108-72-5Relevant articles and documents
An electron-deficient tris(triazole)-based discotic liquid crystal that exhibits fast electron transport
Bala, Indu,De, Joydip,Dhingra, Shallu,Gupta, Santosh Prasad,Pal, Santanu Kumar,Pandey, Upendra Kumar
, p. 5628 - 5632 (2021)
In this study, a C3-symmetric star-shaped discotic mesogen has been reported based on an electron-deficient tris(triazole) central rigid core functionalized with three peripheral trialkoxyphenyl units. The mesogen exhibits an enantiotropic columnar hexagonal (Colh) phase that can sustain over a significant temperature range. When used in space-charge limited current (SCLC) devices, it showed ambipolar charge transport behavior with high electron mobility (μe) of 1.61 × 10-2 cm2 V-1 s-1 at ambient temperature. The finding is sufficiently significant to warrant their use in organic electronic devices.
Selective reduction of one, two, or three nitro groups in 1,3,5-trinitrobenzene with hydrazine hydrate
Shakhnes,Vorob'Ev,Shevelev
, p. 938 - 939 (2006)
A method was developed for successive selective reduction of one, two, or three nitro groups in 1,3,5-trinitrobenzene with hydrazine hydrate in the presence of iron chloride and charcoal. This method provides an approach to the one-pot synthesis of 3,5-dinitroaniline, 1,3-diamino-5-nitrobenzene, or 1,3,5-triaminobenzene from 1,3,5-trinitrobenzene. Springer Science+Business Media, Inc. 2006.
The composition of transformation products of 2,4,6-trinitrobenzoic acid in the aqueous-phase hydrogenation over Pd/C catalysts
Talsi, Valentin P.,Belskaya, Olga B.,Yurpalov, Vyacheslav L.
, p. 84 - 96 (2020)
Due to a detailed analysis of NMR spectra of the reaction solutions with different composition obtained by the aqueous-phase catalytic (Pd/C) hydrogenation of 2,4,6-trinitrobenzoic acid, the intermediate compounds were identified and a more substantiated mechanism was proposed for the formation of the main reaction products—1,3,5-triaminobenzene and cyclohexane-1,3,5-trione trioxime. The condensation of the 1,3,5-triaminobenzene molecules produced by a complete hydrogenation of 2,4,6-trinitrobenzoic acid was shown to result in the formation of a paramagnetic heterocyclic compound.
Transformation pathways of 2,4,6-trinitrobenzoic acid in the aqueous-phase hydrogenation over Pd/C catalyst
Belskaya, Olga B.,Talsi, Valentin P.,Mironenko, Roman M.,Rodionov, Vladimir A.,Sysolyatin, Sergey V.,Likholobov, Vladimir A.
, p. 190 - 199 (2016)
Results of the catalytic hydrogenation of 2,4,6-trinitrobenzoic acid (TNBA) in the presence of 1% Pd/C catalyst with analysis of the reaction products at the steps corresponding to the consumption of 1, 3, 5, 6, 8 and 9 mols of hydrogen per mol of TNBA are presented. Numerous reaction intermediates were identified using the 1H and 13C NMR spectroscopy; the reaction mixture composition was assessed quantitatively at different steps of the hydrogenation. The data obtained were used to propose a scheme of TNBA transformations over the Pd/C catalyst in the aqueous-phase reaction conditions. The data on the component composition at different steps of TNBA hydrogenation are important to understand the process chemistry, to explore the possibility of selective formation of different types of intermediate nitroamino compounds, and to synthesize high-performance catalysts for the hydrogenation of aromatic polynitro compounds.
Effect of the reduction conditions of the supported palladium precursor on the activity of Pd/C catalysts in hydrogenation of sodium 2,4,6-trinitrobenzoate
Belskaya,Mironenko,Gulyaeva,Trenikhin,Likholobov
, (2018)
The study addresses the effect of the reduction conditions of palladium polynuclear hydroxo complexes (PHC) supported on the Sibunit carbon material on the dispersion of the metal particles and the activity of 0.5%Pd/Sibunit catalysts in the selective hyd
Dynamic self-assembled polymer: HCl responsive inversion of supramolecular polymer handedness
Paikar, Arpita,Haldar, Debasish
, p. 47170 - 47176 (2017)
A series of discotic tricarboxyamides with varied amino acid side arm functionality and their HCl responsive diverse self-assembly behavior and formation of dynamic polymer is studied. Discotic trisamide 1 obtained from Boc protected l-Lys self-assembled into a long fibrillar aggregate-like supramolecular P helical polymer. However, on addition of HCl, the supramolecular helical handedness of the assemblies is completely inverted. Irrespective of the chiral centres configuration, supramolecular chiral bias is arising from molecular conformations. FE-SEM reveals the formation of right handed entangled polymeric fibers. However, left handed entangled fibers have appeared on addition of 0.12 M HCl. The trisamide 2 containing Boc protected l-Trp exhibits disk like morphology both in the presence and absence of 0.12 M HCl and does not show a change of supramolecular handedness. This demonstrates how remarkably distinct morphologies originate from stimuli responsive building blocks assembled in a subtly different manner.
An unusual reduction route of 2,4,6-trinitrobenzoic acid under conditions of aqueous-phase hydrogenation over Pd/Sibunit catalyst
Mironenko,Belskaya,Talzi,Rodionov,Sysolyatin,Likholobov
, p. 1535 - 1540 (2016)
For the first time it was established that the catalytic hydrogenation of 2,4,6-trinitrobenzoic acid to 1,3,5-triaminobenzene can proceed via the formation of aromatic hydroxyamines and cyclohexane-1,3,5-trione trioxime. As a result of aqueous-phase hydrogenation of sodium salt of 2,4,6-trinitrobenzoic acid in the presence of 5%Pd/Sibunit catalyst at a temperature of 323 K and pressure of 0.5 MPa, a trioxime in high yield (about 70 %) was obtained. Due to high selectivity to cyclohexane-1,3,5-trione trioxime the catalytic hydrogenation of sodium salt of 2,4,6-trinitrobenzoic acid can be considered as a new method for its synthesis.
Synthesis and Two-Dimensional Chiral Surface Self-Assembly of a π-Conjugated System with Three-Fold Symmetry: Benzotri(7-Azaindole)
Rodríguez, Luis M.,Gómez, Paula,Más-Montoya, Miriam,Abad, José,Tárraga, Alberto,Cerdá, Jorge I.,Méndez, Javier,Curiel, David
, p. 1782 - 1788 (2021)
The synthesis of a novel expanded π-conjugated system, namely benzotri(7-azaindole), BTAI, is reported. Its C3h symmetry along with the integration of six complementary donor and acceptor N?H???N hydrogen bonds in the conjugated structure promote the 2D self-assembly on Au(111) over extended areas. Besides, a perfect commensurability with the gold lattice endows the physisorbed molecular film with a remarkable stability. The structural features of BTAI result in two levels of surface chirality: Firstly, the molecules become chiral upon adsorption on the surface. Then, due to the favorable N?H???N hydrogen bond-directed self-assembly, along with the relative molecular rotation with respect to the substrate, supramolecular chirality manifests in two mirror enantiomorphous domains. Thus, the system undergoes spontaneous chiral resolution. LEED and STM assisted by theoretical simulations have been employed to characterize in detail these novel 2D conglomerates with relevant chiral properties for systems with C3h symmetry.
Gold nanoparticles-supported histamine-grafted monolithic capillaries as efficient microreactors for flow-through reduction of nitro-containing compounds
Liu,Guerrouache,Kebe,Carbonnier,Le Droumaguet
, p. 11805 - 11814 (2017)
A histamine functionalized monolith was synthesized within a micro-sized channel as a permeable support for the immobilization of 5, 20 and 100 nm-sized gold nanoparticles and the resulting nanostructured hybrid monoliths were applied as microreactors for the catalytic reduction of nitro-derivatives. The whole synthetic pathway of the composite materials relies on (i) UV-induced polymerization of N-acryloxysuccinimide and ethylene glycol dimethacrylate in toluene, (ii) surface grafting of histamine through nucleophilic substitution of hydroxysuccinimide leaving groups, and (iii) specific adsorption of citrate-stabilized colloidal gold nanoparticles. The achievement of the successive synthetic steps was ascertained by using a combination of experimental techniques providing information about the chemical composition (FTIR, Raman, and EDX) and porosity and surface-dispersion (SEM) of gold nanoparticles. Of particular interest, it is shown that surface-grafted histamine units exhibit strong affinity towards gold nanoparticles and allow homogeneous and dense dispersion of 5 and 20 nm sized nanoparticles. Consequently, the gold nanoparticle size-dependence of the catalytic activity (conversion of nitro and di-nitro aromatic compounds into the corresponding amino and di-amino-derivatives) was demonstrated, highlighting the utmost importance of controlling the dispersion of nano-catalysts on the support surface, while histamine protonation was also evidenced as a parameter of paramount importance regarding nanogold surface density and thus resulting catalytic activity. Histamine protonation notably allows the generation of electrostatic interactions between citrate-coated gold nanoparticles and thus-formed positive charges at the monolith surface.
Synthesis of Azapolycyclic Systems Based on the Indolizino[3,4-b]quinoline Skeleton - A Diastereoselective Entry to Potential Oligodentate Artificial Receptors
Temme, Oliver,Dickner, Tim,Laschat, Sabine,Froehlich, Roland,Kotila, Sirpa,Bergander, Klaus
, p. 651 - 659 (1998)
A convenient diastereoselective synthetic route to the molecular tweezer bis(indolizino[3,4-b]quinolyl)methane 9 and the rigid indolizino[7′,8′:2,3]quinolino[8,7-h]indolizino[8,7-b]quinolines 14, 15 as potential receptor molecules has been developed, involving double imine condensation followed by Lewis acid catalyzed biscyclization of prolinal-derived bis-(imines) 8 and 13, respectively. Whereas the use of SnCl4 leads to the formation of the planar polycycle 15, the corresponding concave product 14 is formed in the presence of EtAlCl2. Both compounds 14, 15, as well as tweezer 9 have been characterized by X-ray crystal-structure analysis. Although tris(imines) 20, 24 derived from 1,3,5-triaminobenzene (18) and tris(4-aminophenyl)amine (23) could be obtained similarly by molecular sieve-catalyzed condensation, the corresponding triscyclization could not be achieved. However, by attaching preformed indolizino[3,4-b]quinoline subunits 25 and 31 to an aromatic core, the bidentate receptors 30, 33 and the tentacle molecule 28 were accessible.
