60532-63-0

Usage

Uses

Used in Chemical Synthesis:
Tetrakis(4-aminophenyl)methane is used as a synthetic material intermediate for the production of advanced organic compounds and materials.
Used in the Synthesis of COF-320:
Tetrakis(4-aminophenyl)methane is used as a precursor in the synthesis of the structurally similar COF-320, which is a covalent organic framework that differs from COF-300 by the length of the linear dialdehyde linker, employing 4-4’-biphenyldicarboxyaldehyde instead of terephthalaldehyde.
Used in the Synthesis of Novel Tetrahedral COFs:
Tetrakis(4-aminophenyl)methane is used alongside tetrakis(4-formylphenyl)methane as a tetrahedral aldehyde monomer to explore the synthesis of a novel tetraaminetetraaldehyde covalent organic framework (COF), expanding the range of materials available for various applications.

Preparation

synthesis of Tetrakis(4-aminophenyl)methane: Tetrakis-(4-nitrophenyl)methane (1.5 g, 3 mmol) was dissolved in tetrahydrofuran (100 ml), and Raney nickel (10 g) was added to the solution while stirring under nitrogen. Hydrazine monohydrate (2 g, 0.04 mol) was slowly added via syringe, and the mixture was refluxed for 4 h. The mixture was filtered while hot and washed with ethanol. The filtrate was dried in vacuo. The crude product was subsequently washed with ethanol (50 ml) and dried in vacuo to afford Tetrakis(4-aminophenyl)methane as a white solid (0.92 g, 81% yield).

Upstream product

• 630-76-2 tetraphenylmethane 
• 76-84-6 triphenylmethyl alcohol 
• 22948-06-7 4-tritylaniline 
• 62-53-3 aniline 
• 76-83-5 trityl chloride 
• 945018-87-1 4-tritylaniline hydrochloride 
• 60532-62-9 tetrakis(4-nitrophenyl)methane 

Downstream Products

• 53184-78-4 4,4′,4″,4'-methanetetrayltetraphenol 
• 666235-02-5 tetrakis[4-[(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenyl]methane 
• 697746-87-5 tetrakis(4-isocyanatophenyl)methane 
• 1000190-45-3 tetrakis(4-azidophenyl)methane 
• 1293383-77-3 N,N',N'',N'''-(4,4',4'',4'''-methanetetrayltetrakis(benzene-4,1-diyl))tetrakis(2,4,5-trimethyl-N-(2,4,5-trimethylphenyl)aniline) 
• 1582774-32-0 C₄₉H₃₆N₈ 

Relevant academic research and scientific papers

Star-like oriented chromophores

The tetrahedral arrangement of perylene bisimide chromophores gives a novel molecular system of antennae for the conversion of difuse solar radiation. A detailed analysis of their UV/Vis spectra gives an impression of the consolidation of the single chromophores.

Three-Dimensional Radical Covalent Organic Frameworks as Highly Efficient and Stable Catalysts for Selective Oxidation of Alcohols

With excellent designability, large accessible inner surface, and high chemical stability, covalent organic frameworks (COFs) are promising candidates as metal-free heterogeneous catalysts. Here, we report two 3D radical-based COFs (JUC-565 and JUC-566) in which radical moieties (TEMPO) are uniformly decorated on the channel walls via a bottom-up approach. Based on grafted functional groups and suitable regular channels, these materials open up the application of COFs as highly efficient and selective metal-free redox catalysts in aerobic oxidation of alcohols to relevant aldehydes or ketones with outstanding turn over frequency (TOF) up to 132 h?1, which has exceeded other TEMPO-modified catalytic materials tested under similar conditions. These stable COF-based catalysts could be easily recovered and reused for multiple runs. This study promotes potential applications of 3D functional COFs anchored with stable radicals in organic synthesis and material science.

Zinc(ii) and cadmium(ii) amorphous metal-organic frameworks (aMOFs): Study of activation process and high-pressure adsorption of greenhouse gases

Two novel amorphous metal-organic frameworks (aMOFs) with chemical composition {[Zn2(MTA)]·4H2O·3DMF}n (UPJS-13) and {[Cd2(MTA)]·5H2O·4DMF}n (UPJS-14) built from Zn(ii) and Cd(ii) ions and extended tetrahedral tetraazo-tetracarboxylic acid (H4MTA) as a linker were prepared and characterised. Nitrogen adsorption measurements were performed on as-synthesized (AS), ethanol exchanged (EX) and freeze-dried (FD) materials at different activation temperatures of 60, 80, 100, 120, 150 and 200 °C to obtain the best textural properties. The largest surface areas of 830 m2 g-1 for UPJS-13 (FD) and 1057 m2 g-1 for UPJS-14 (FD) were calculated from the nitrogen adsorption isotherms for freeze-dried materials activated at mild activation temperature (80 °C). Subsequently, the prepared compounds were tested as adsorbents of greenhouse gases, carbon dioxide and methane, measured at high pressures. The maximal adsorption capacities were 30.01 wt% CO2 and 4.84 wt% CH4 for UPJS-13 (FD) and 24.56 wt% CO2 and 6.38 wt% CH4 for UPJS-14 (FD) at 20 bar and 30 °C.

Cu(ii)Cl2containing bispyridine-based porous organic polymer support preparedviaalkyne-azide cycloaddition as a heterogeneous catalyst for oxidation of various olefins

A new type of porous organic polymer (POP) based heterogeneous catalystCu-POPwas prepared by immobilizing Cu(ii)Cl2into bpy containing POP preparedviaalkyne-azide cycloaddition. This new catalyst showed efficient catalytic activities and outstanding reusability. Remarkably, one batch ofCu-POPwas continuously used for all olefins without losing its activity by simply washing.

Tetrahedral octaamine compound and manufacturing method thereof

Disclosed is a method for preparing octaamine compound, which comprises the steps of: (a) introducing a nitro group by nitrating tetraphenylmethine; (b) obtaining tetrakis(4-aminophenyl)methane by reducing the nitro group; (c) introducing an o-nitro group by nitrating the tetrakis(4-aminophenyl)methane; and (d) reducing the o-nitro group, wherein the step (d) is performed under a strong acid condition. Also, disclosed is an octaamine compound represented by chemical formula 1, wherein central atom is C and o-phenylenediamine is four-substituted to the central atom.COPYRIGHT KIPO 2020

Scalable Synthesis of Tetrapodal Octaamine

An effective and high-yielding synthesis of an air stable tetrapodal octaamine, a rigid shape-persistent molecule with four ortho-phenylenediamine moieties is reported. It can be potentially transformed into a wide range of benzimidazole, benzotriazole, and pyrazine derivatives for practical applications.

Luminescent covalent organic framework as a recyclable turn-off fluorescent sensor for cations and anions in aqueous solution

Covalent organic frameworks (COFs) have shown great potential for use in ion sensing; however, applications of existing COFs are limited to sensing either cations or anions. In this study, a three-dimensional COF, COF-TT, is constructed by reacting the bis(tetraoxacalix[2]arene[2]triazine) core with tetra(p-aminophenyl)methane to provide a luminescent sensor. COF-TT exhibits ultrahigh thermal stability and exceptional chemical stability in aqueous solutions over a broad pH range from 2 to 14, which signifies immense practical potential for sensing applications. Excellent selectivity and high sensitivity of COF-TT toward Fe3+ cations and CrO42-, Cr2O72-, and MnO4- anions are evident via luminescence quenching. COF-TT also exhibits excellent recyclability in terms of washing and re-exposure cycles. Both experimental data and theoretical calculations are employed to unveil the mechanisms of the quenching effect and sensing properties of COF-TT.

Three-Dimensional Tetrathiafulvalene-Based Covalent Organic Frameworks for Tunable Electrical Conductivity

The functionalization of three-dimensional (3D) covalent organic frameworks (COFs) is essential to broaden their applications. However, the introduction of organic groups with electroactive abilities into 3D COFs is still very limited. Herein we report the first case of 3D tetrathiafulvalene-based COFs (3D-TTF-COFs) with non- or 2-fold interpenetrated pts topology and tunable electrochemical activity. The obtained COFs show high crystallinity, permanent porosity, and large specific surface area (up to 3000 m2/g). Furthermore, these TTF-based COFs are redox active to form organic salts that exhibit tunable electric conductivity (as high as 1.4 × 10-2 S cm-1 at 120 °C) by iodine doping. These results open a way toward designing 3D electroactive COF materials and promote their applications in molecular electronics and energy storage.

Three-dimensional conductive porous organic polymers based on tetrahedral polythiophene for high-performance supercapacitors

Porous organic polymers have become promising electrode materials, but their low surface area and poor electrical conductivity limit their application in high-performance supercapacitors. This study reports the facile synthesis of two porous organic polymers (POP-1 and POP-2) via the condensation of tetra(4-aminophenyl)methane and 2-thenaldehyde or 2,2-bithiophene-5-carboxyaldehyde and their subsequent polymerization. The resulting porous organic polymer materials were characterized using FT-IR, 13C-NMR, X-ray single crystal diffraction, SEM, TEM and N2 adsorption-desorption measurements. This study shows that POP-2 has a diamond topological structure with a regular morphology and a wealth of pores, and a higher BET surface area (342 m2 g-1) when compared with POP-1 (260 m2 g-1). POP-2, when used as an electrode material for supercapacitors, also exhibits a much better electrochemical performance, including higher specific capacitance (332 F g-1) and better cycle stability (capacity retention rate of more than 94% after 10000 successive cycles). These results verify that the structure and electrochemical properties of porous organic polymer materials can be effectively improved by altering the monomers. This study also provides an approach for building various porous organic polymer materials for use in high-performance supercapacitors.

Role of higher aromatic content in modulating properties of cardanol based benzoxazines

Mono-benzoxazine monomers based polybenzoxazines suffer from a lower crosslink density and char yield that especially is further diluted by the presence of longer alkylene chain in cardanol (C). In order to improve the crosslink density, char yield and to understand the role of higher aromatic content vs functionality, a series of cardanol-based benzoxazine monomers were synthesised. The amine condensed with cardanol and paraformaldehyde were aniline (a), 4-triphenylmethylaniline (ta), and tetra-aminophenyl methane (tapm) via solventless methodology. The C-a and C-ta are mono-benzoxazines while C-tapm is a tetra-benzoxazine monomer. The monomers were structurally characterised using FT-IR, 1H and 13C NMR spectroscopy and mass spectrometry. The ring opening polymerisation temperature (ROP) of monomers and thermal stability of resins was determined using DSC and TGA while mechanical properties were determined using rheometry. The curing kinetic study using FT-IR and DSC showed C-ta has intermediate curing behaviour between the C-a and C-tapm. The Ea for curing reaction C-a, C-ta and C-tapm was found to be 143, 126 and 70?kJ/mol. The lowest Ea for curing reaction of C-tapm (tetra-benzoxazine) is due to its highest functionality but C-ta (mono-benzoxazine) has lower Ea than C-a which can be accounted to the presence of more reactive sites provided by the additional aromatic rings in the former. It was found that the incorporation of higher aromatic ring in benzoxazine monomers is another route in enhancing the crosslink density besides higher functionality to modulate their properties.