605-28-7

Basic information

• Product Name: 2,7-dinitroanthraquinone
• Synonyms: 2,7-dinitroanthraquinone;2,7-Dinitro-9,10-anthracenedione;2,7-Dinitro-9,10-anthraquinone;2,7-dinitroanthracene-9,10-dione
• CAS NO: 605-28-7
• Molecular Formula: C₁₄H₆N₂O₆
• Molecular Weight: 298.20724
• EINECS: 210-084-2
• Mol File: 605-28-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 239-240 °C
• Boiling Point: 563.4°C at 760 mmHg
• Flash Point: 294°C
• Appearance: /
• Density: 1.631g/cm³
• Vapor Pressure: 1.02E-12mmHg at 25°C
• Refractive Index: 1.714
• CAS DataBase Reference: 2,7-dinitroanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-dinitroanthraquinone(605-28-7)
• EPA Substance Registry System: 2,7-dinitroanthraquinone(605-28-7)

Safety Data

• Hazardous Substances Data: 605-28-7(Hazardous Substances Data)

Usage

General Description

2,7-dinitroanthraquinone is a synthetic chemical compound that belongs to the class of anthraquinone derivatives. It is commonly used in the production of dyes, particularly in the manufacture of red and violet shades. 2,7-dinitroanthraquinone is characterized by its bright color and high stability, making it suitable for use in textile and paper industries. Additionally, 2,7-dinitroanthraquinone has also been studied for its potential application as a photosensitizer in organic photovoltaic devices, due to its strong light absorption properties. However, it is important to handle this chemical with care, as it is toxic and can cause skin and eye irritation upon contact.

InChI:InChI=1/C14H6N2O6/c17-13-9-3-1-7(15(19)20)5-11(9)14(18)12-6-8(16(21)22)2-4-10(12)13/h1-6H

Upstream product

• 120-12-7 anthracene 
• 84-65-1 9,10-phenanthrenequinone 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 22582-76-9 anthracene-9-sulfonic acid 
• 860531-67-5 9,9,10,10-tetraisobutyl-2,7-dinitro-9,10-dihydro-anthracene 
• 98-95-3 nitrobenzene 
• 90-44-8 anthracen-9(10H)-one 

Downstream Products

• 605-42-5 2,7-dibromo-9,10-anthraquinone 
• 572-93-0 2,7-dihydroxy-anthraquinone 
• 605-44-7 2,7-diaminoanthraquinone 

Relevant articles and documents

On-Surface Synthesis and Collective Spin Excitations of a Triangulene-Based Nanostar

Triangulene nanographenes are open-shell molecules with predicted high spin state due to the frustration of their conjugated network. Their long-sought synthesis became recently possible over a metal surface. Here, we present a macrocycle formed by six [3]triangulenes, which was obtained by combining the solution synthesis of a dimethylphenyl-anthracene cyclic hexamer and the on-surface cyclodehydrogenation of this precursor over a gold substrate. The resulting triangulene nanostar exhibits a collective spin state generated by the interaction of its 12 unpaired π-electrons along the conjugated lattice, corresponding to the antiferromagnetic ordering of six S=1 sites (one per triangulene unit). Inelastic electron tunneling spectroscopy resolved three spin excitations connecting the singlet ground state with triplet states. The nanostar behaves close to predictions from the Heisenberg model of an S=1 spin ring, representing a unique system to test collective spin modes in cyclic systems.

Light-Induced Charge Separation in Densely Packed Donor-Acceptor Coordination Cages

Photon-powered charge separation is achieved in a supramolecular architecture based on the dense packing of functional building blocks. Therefore, self-assembled dimers of interpenetrated coordination cages consisting of redoxactive chromophors were synthesized in a single assembly step starting from easily accessible ligands and Pd(II) cations. Two backbones consisting of electron rich phenothiazine (PTZ) and electron deficient anthraquinone (ANQ) were used to assemble either homo-octameric or mixed-ligand double cages. The electrochemical and spectroscopic properties of the pure cages, mixtures of donor and acceptor cages and the mixed-ligand cages were compared by steady-state UV-vis and transient absorption spectroscopy, supported by cyclic voltammetry and spectroelectrochemistry. Only the mixed-ligand cages, allowing close intra-assembly communication between the donors and acceptors, showed the evolution of characteristic PTZ radical cation and ANQ radical anion features upon excitation in the transient spectra. In contrast, excitation of the mixtures of the homo-octameric donor and acceptor cages in solution did not lead to any signs of electron transfer. Densely packed photo- and redox-functional self-assemblies promise molecular-level control over the morphology of the charge separation layer in future photovoltaic applications.

Synthesis, characterization and photovoltaic behavior of platinum acetylide polymers with electron-deficient 9,10-anthraquinone moiety

A new class of soluble, solution-processable platinum(II) acetylide polymers functionalized with electron-deficient 9,10-anthraquinone spacer and their corresponding diplatinum model complexes were synthesized and characterized. The organometallic polymers exhibit good thermal stability and show low-energy broad absorption bands in the visible region. The effect of the presence of thiophene rings along the polymer chain on the optical and photovoltaic properties of these metallated materials was examined. The low-bandgap polymer with thiophene-anthraquinone-thiophene (donor-acceptor- donor) fragment can serve as a good electron donor for fabricating bulk heterojunction polymer solar cells by blending with a methanofullerene electron acceptor. At the same donor:acceptor blend ratio of 1:4, the light-harvesting ability and solar cell efficiency notably increase when the anthraquinone ring is sandwiched by two thiophene units. Photoexcitation of such polymer solar cells results in a photoinduced electron transfer from the π-conjugated metallopolymer to [6,6]-phenyl C61-butyric acid methyl ester with power conversion efficiency up to ～ 0.35%. For safety concern, these metallopolymers were also tested for possible cytotoxicity and they do not show significant cytotoxic activity on human liver derived cells and skin keratinocytes at reasonable doses, rendering these functional materials safe to use in practical devices.