60532-62-9

Usage

Uses

Used in Organic Synthesis:
Tetrakis(4-nitrophenyl)methane is used as a building block for the synthesis of tetrakis(4-aminophenyl)methane, which is an important compound in organic chemistry. The adaptability of TNPM in different solvents allows for efficient synthesis processes.
Used in Host-Guest Chemistry:
Due to its structural adaptability, tetrakis(4-nitrophenyl)methane can be used as a new host material in host-guest chemistry. This allows for the development of new supramolecular systems with potential applications in various fields, such as sensing, drug delivery, and molecular recognition.
Used in Crystal Engineering:
Tetrakis(4-nitrophenyl)methane can be employed in crystal engineering to design and construct novel crystal structures with specific properties. Its adaptability in different solvents and its tetrahedral geometry make it a promising candidate for creating new materials with tailored characteristics.

Preparation

The synthesis procedure for Tetrakis-(4-nitrophenyl)methane: Tetraphenylmethane (4.8g, 15.0 mmol) was slowly added to fuming nitric acid (25 ml) stirred rigorously in a salt/ice bath of ~-5°C. Then, a mixture of acetic anhydride and glacial acetic acid (1:2, 25 ml) was added slowly to the mixture. After stirring at -5°C for 15 min, glacial acetic acid (80 ml) was added, and the suspension was further stirred for 5 min. The mixture was filtered on a glass frit, washed with acetic acid (2 x 100 ml), methanol (2 x 100 ml), and chilled tetrahydrofuran (2 x 50 ml) and dried in vacuo to afford a cream color solid (3.2 g, 43% yield).

Upstream product

• 630-76-2 tetraphenylmethane 
• 62-53-3 aniline 
• 76-84-6 triphenylmethyl alcohol 
• 22948-06-7 4-tritylaniline 
• 76-83-5 trityl chloride 
• 945018-87-1 4-tritylaniline hydrochloride 

Downstream Products

• 53184-78-4 4,4′,4″,4'-methanetetrayltetraphenol 
• 1236194-08-3 C₅₃H₅₆N₄O₁₆ 
• 1000190-45-3 tetrakis(4-azidophenyl)methane 
• 1582774-32-0 C₄₉H₃₆N₈ 
• 666235-02-5 tetrakis[4-[(2,4-dichloro-1,3,5-triazin-6-yl)amino]phenyl]methane 
• 698348-40-2 tetra(4-amino-3,5-dibromo)phenylmethane 
• 697746-87-5 tetrakis(4-isocyanatophenyl)methane 
• 60532-63-0 tetrakis(4-aminophenyl)methane 

Relevant academic research and scientific papers

High anhydrous proton conductivity of imidazole-loaded mesoporous polyimides over a wide range from subzero to moderate temperature

On-board fuel cell technology requires proton conducting materials with high conductivity not only at intermediate temperatures for work but also at room temperature and even at subzero temperature for startup when exposed to the colder climate. To develop such materials is still challenging because many promising candidates for the proton transport on the basis of extended microstructures of water molecules suffer from significant damage by heat at temperatures above 80 °C or by freeze below -5 °C. Here we show imidazole loaded tetrahedral polyimides with mesopores and good stability (Im@Td-PNDI 1 and Im@Td-PPI 2) exhibiting a high anhydrous proton conductivity over a wide temperature range from -40 to 90 °C. Among all anhydrous proton conductors, the conductivity of 2 is the highest at temperatures below 40 °C and comparable with the best materials, His@[Al(OH)(1,4-ndc)]n and [Zn3(H2PO4)6(H2O)3](Hbim), above 40 °C.

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.

Inclusion compounds of tetrakis(4-nitrophenyl)methane: C-H···O networks, pseudopolymorphism, and structural transformations

Tetrakis(4-nitrophenyl)methane is a new host material with considerable structural adaptability over a range of solvents. The crystal structures of 14 of these solvates have been determined and classified into three groups. The diamondoid group, wherein t

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.

A novel 3D covalent organic framework membrane grown on a porous α-Al2O3 substrate under solvothermal conditions

A novel approach to grow a 3D COF-320 membrane on a surface-modified porous α-Al2O3 substrate is developed. A compact and uniform COF-320 membrane with a layer thickness of ～4 μm is obtained. This is the first reported 3D COF functional membrane fabricated successfully on a common porous α-Al2O3 ceramic support. The gas permeation results indicate that the gas transport behavior is mainly governed by the predicted Knudsen diffusion process due to the large nanopores of 3D COF-320.

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.

Tetrahedral n-type materials: Efficient quenching of the excitation of p-type polymers in amorphous films

Tetrahedral naphthalenediimide compound 1 has been synthesized as an example of a new class of amorphous n-type materials, in which the nondirectionality obtained by its shape is decoupled from its optoelectronic properties. 1 forms bicontinuous films with p-type polymers and effectively quenches the excited state, yielding long-lived mobile charge carriers on pulsed illumination. Copyright

Microporous Organic Polyimides for CO2 and H2O Capture and Separation from CH4 and N2 Mixtures: Interplay between Porosity and Chemical Function

Porous polyimides have been considered to be a promising material class for gas capture and sequestration, leading to the synthesis of a substantial number of individual networks with noteworthy sorption properties. In spite of these efforts, the vision of a chemical control of adsorption and desorption of small molecules, in particular, for the competing uptake of technical relevant gas mixtures, is still hardly investigated. Here, we present a systematic study of five new polyimide networks based on a set of linkers with chemical functionalities covering the full range from hydrophobic to hydrophilic interactions. The corresponding microporous organic polyimides (MOPI-I to -V) were synthesized successfully based on a condensation reaction between amino and anhydride linker molecules in m-cresol at high temperatures, resulting in cross-linking degrees beyond 95% in all cases. Argon and carbon dioxide isotherms reveal surface areas up to 940 m2/g with ultramicroporosity, about 50% microporosity and high thermal stabilities under air with decomposition temperatures up to 480 °C. Sorption screening for variable temperatures revealed remarkable uptakes for carbon dioxide up to 3.8 mmol/g and water vapor up to 19.5 mmol/g combined with a smooth gate opening around 0.25 p/p0 for MOPI-IV. In contrast, for MOPI-V the water vapor uptake decreases down to 7 mmol/g. Interestingly, the trend of the selectivities calculated by IAST and Henry does not correlate with the uptake behavior. For instance, MOPI-I and MOPI-III exhibit with 78 and 13 the highest CO2 over N2 and CH4 Henry selectivities, although their CO2 uptake is around 3.0 mmol/g. In total, we attribute the sorption properties for this class of materials mainly to the void size and shape within the ultramicroporous region. The chemical environment of the surfaces seems to have little influence on the uptake and a stronger effect on the separation behavior.

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.

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.