20440-91-9

Usage

Uses

Used in Organic Photovoltaic Devices:
4,4'-Dimethoxy-4''-nitrotriphenylamine is used as an electron donor material for enhancing the performance of organic photovoltaic devices. Its electron-donating characteristics contribute to the efficiency of these devices by facilitating charge transfer and improving overall energy conversion.
Used in Organic Light-Emitting Diodes (OLEDs):
In the field of OLEDs, 4,4'-Dimethoxy-4''-nitrotriphenylamine is utilized for its potential to improve the performance and efficiency of these light-emitting devices. Its properties may contribute to better charge transport and emission characteristics, leading to brighter and more energy-efficient displays.
Used in Electronic Applications:
Beyond photovoltaics and OLEDs, 4,4'-Dimethoxy-4''-nitrotriphenylamine is also considered for use in other electronic applications. Its unique structure and properties may offer advantages in the development of new electronic materials and components, such as in sensors, transistors, or other integrated circuit elements.
Used in Research Studies:
4,4'-Dimethoxy-4''-nitrotriphenylamine serves as a subject of research for scientists exploring new materials and their potential applications in various technological fields. Its unique properties and reactivity make it an interesting candidate for studies aimed at understanding and improving the performance of organic electronic materials.

InChI:InChI=1/C20H18N2O4/c1-25-19-11-7-16(8-12-19)21(17-9-13-20(26-2)14-10-17)15-3-5-18(6-4-15)22(23)24/h3-14H,1-2H3

Upstream product

• 696-62-8 para-iodoanisole 
• 6686-68-6 2-[(4-methoxyphenyl)amino]-5-nitrobenzoic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 99-09-2 3-nitro-aniline 
• 100-01-6 4-nitro-aniline 
• 101-70-2 bis(4-methoxyphenyl)amine 
• 350-46-9 4-Fluoronitrobenzene 

Downstream Products

• 1609011-89-3 C₂₇H₂₂N₄O₇ 
• 1609011-91-7 4-(3,5-diaminobenzamido)-4',4''-dimethoxytriphenylamine 

Relevant academic research and scientific papers

A new series of azobenzene-bridged metal-free organic dyes and application on DSSC

A series of novel azobenzene-based dyes were designed and synthesized using azobenzene as the π-spacer unit to connect diarylamino and cyanoacetic acids for construction of the D–π–A conformation. The introduction of a thienyl into the anchor group (A) co

Copper(I)-USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O-, N-, S-, and C-Arylation Reactions: Scope and Application to Total Synthesis

The copper(I)-doped zeolite CuI-USY proved to be a versatile, efficient, and recyclable catalyst for various Ullmann-type coupling reactions. Easy to prepare and cheap, this catalytic material enables the arylation and heteroarylation of diverse O-, N-, S-, and C-nucleophiles under ligand-free conditions while exhibiting large functional group compatibility. The facility of this catalyst to promote C-O bond formation was further demonstrated with the total synthesis of 3-methylobovatol, a naturally occurring diaryl ether of biological relevance. From a mechanistic viewpoint, two competitive pathways depending on the nature of the nucleophile and consistent with the obtained results have been proposed.

Design rules for the preparation of low-cost hole transporting materials for perovskite solar cells with moisture barrier properties

The current state-of-the-art hole transporting materials (HTM) for perovskite solar cells are generally synthesized via cross-coupling reactions that require expensive catalysts, inert reaction conditions and extensive product purification, resulting in h

Light-driven electron injection from a biotinylated triarylamine donor to [Ru(diimine)3]2+-labeled streptavidin

Electron transfer from a biotinylated electron donor to photochemically generated Ru(iii) complexes covalently anchored to streptavidin is demonstrated by means of time-resolved laser spectroscopy. Through site-selective mutagenesis, a single cysteine res

A low cost azomethine-based hole transporting material for perovskite photovoltaics

Most hole transporting materials (HTMs) prepared for perovskite solar cell applications are synthesized via cross-coupling reactions that require expensive transition metal catalysts, inert reaction conditions and extensive product purification; making la

Organic mixed valency in quadruple hydrogen-bonded triarylamine dimers bearing ureido pyrimidinedione moieties

Quadruple hydrogen-bonding interactions stabilized the mixed-valence states of dimers of triarylamine derivatives bearing an ureido pyrimidinedione moiety without any electronic coupling. This study represents the first example of proton-coupled "organic"

Synthesis and electrochromic properties of aromatic polyimides bearing pendent triphenylamine units

A series of aromatic polyimides with pendent triphenylamine group were synthesized from equimolar mixtures of 4,4′-oxydianiline (ODA) and 4-(3,5-diaminobenzamido)triphenylamine (4), 4-(3,5-diaminobenzamido)-4′, 4″-di-tert-butyltriphenylamine (t-Bu-4) or 4-(3,5-diaminobenzamido)- 4′,4″-dimethoxytriphenylamine (MeO-4) with two aromatic tetracarboxylic dianhydrides (DSDA or 6FDA) via a conventional two-step procedure that included a ring-opening polyaddition to give poly(amic acid)s, followed by chemical imidization. These polyimides exhibited good solubility in polar organic solvents and could be solution-cast into flexible and strong films. They showed excellent thermal stability, with Tg values in the range of 284-309°C. The polyimides derived from diamines t-Bu-4 and MeO-4 exhibited reversible electrochemical oxidation, accompanied by strong color changes with high contrast ratio and electrochromic stability. For the polyimides derived from diamine 4, the coupling reaction between the triphenylamine radical cations occurred during the oxidative process forming a tetraphenylbenzidine structure, which resulted in an additional oxidation state and color change together with enhanced near-IR absorption at fully oxidized state.

The hierarchical self-assembly of charge nanocarriers: A highly cooperative process promoted by visible light

Let there be more light: Triarylamine-based building blocks respond to visible-light exposure by the formation of cationic radicals that hierarchically self-assemble into molecular wires, which in turn combine within larger fibers (see picture). The stimu

Novel anodic electrochromic aromatic polyamides with multi-stage oxidative coloring based on N,N,N′,N′-tetraphenyl-p-phenylenediamine derivatives

A series of novel aromatic polyamides with pendent 4,4′-dimethoxy- substituted triphenylamine (TPA) units were prepared via the direct phosphorylation polycondensation from a new dicarboxylic acid monomer, N,N-bis(4-carboxyphenyl)-N′,N′-di(4-methoxyphenyl)-1, 4-phenylenediamine (4), and various aromatic diamines. These polyamides were amorphous with good solubility in many organic solvents, such as N-methyl-2-pyrrolidinone (NMP) and N,N-dimethylacetamide (DMAc), and could be solution-cast into flexible polymer films. They had excellent levels of thermal stability associated with their relatively high glass-transition temperatures (233-308 °C). These polymers exhibited strong UV-vis absorption bands at 351-363 nm in NMP solution. Their photoluminescence spectra showed maximum bands around 450-504 nm. The hole-transporting and electrochromic properties are examined by electrochemical and spectroelectrochemical methods. Cyclic voltammograms of the polyamide 6g prepared from the dicarboxylic acid monomer (4) with a structurally similar diamine monomer N,N-bis(4-aminophenyl)-N′, N′-di(4-methoxyphenyl)-1,4-phenylenediamine (5g) exhibited four reversible oxidation redox couples in acetonitrile solution at Eonset = 0.35, E1/2 = 0.64, 0.84, and 0.99 V, respectively. After over 3000 cyclic switches for green color, the films of polyamide 6g still showed excellent continuous cyclic stability of electrochromism.

An inexpensive and efficient copper catalyst for N-arylation of amines, amides and nitrogen-containing heterocycles

An inexpensive and efficient catalyst system has been developed for the N-arylation of nitrogen-containing compounds including a variety of amines, amides, indole and imidazole. This simple protocol uses CuI as the catalyst, commercial available pipecolinic acid as the new ligand, K2CO 3 as the base and DMF as the solvent.