7044-91-9

Usage

Uses

Used in Optoelectronic Applications:
9,10-Anthracenedicarboxaldehyde is used as an aggregation-induced emission luminogens (AIEgens) for its ability to enhance fluorescence in the aggregated state. This property makes it suitable for applications in optoelectronic devices, such as organic light-emitting diodes (OLEDs) and sensors, where efficient light emission is required.
Used in Material Science:
9,10-Anthracenedicarboxaldehyde is used as a reagent in the preparation of porous imine-linked networks (PINs). Its role in the formation of these networks is crucial for creating materials with tailored porosity and specific chemical functionalities, which can be utilized in various applications, such as gas storage, catalysis, and separation processes.

InChI:InChI=1/C16H10O2/c17-9-15-11-5-1-2-6-12(11)16(10-18)14-8-4-3-7-13(14)15/h1-10H

Upstream product

• 523-27-3 9,10-Dibromoanthracene 
• 34373-96-1 9,10-dibromomethylanthracene 
• 20678-93-7 (E)-Dihydroxy-11,12 Ethano-9,10 dihydro-9,10 Anthracene 
• 781-43-1 9,10-dimethylanthracene 
• 120-12-7 anthracene 
• 5675-70-7 cis-9,10-dihydro-9,10-ethanoanthracene-11,12-diol cyclic carbonate 
• 10387-13-0 9,1-bis(chloromethyl)anthracene 
• 108-03-2 1-Nitropropane 
• 1217-45-4 9,10-Dicyanoanthracene 
• 68-12-2 N,N-dimethyl-formamide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 84-65-1 9,10-phenanthrenequinone 
• 56588-78-4 trans-dispiro[oxirane-2,9'[10'H]-anthracene-10',2-oxirane] 
• 10273-85-5 9,10-bis(hydroxymethyl)anthracene 

Downstream Products

• 10273-82-2 (E,E)-9,10-Bis(styryl)anthracene 
• 33501-47-2 9,10-bis((E)-4-methylstyryl)anthracene 
• 106480-96-0 9,10-Bis-(1,4-dihydroxy-4,4-diphenyl-but-2-inyl)-anthracen 
• 113308-38-6 9,10‐bis((E)‐2‐(pyridin‐4‐yl)vinyl)anthracene 
• 136384-78-6 10-[(E)-2-(4-Nitro-phenyl)-vinyl]-anthracene-9-carbaldehyde 
• 136384-80-0 9,10-bis(4-methoxystyryl)anthracene 
• 136384-81-1 9,10-bis((E)-4-chlorostyryl)anthracene 
• 101789-38-2 9,10-bis(1-hydroxymethyl)anthracene 
• 84-65-1 9,10-phenanthrenequinone 
• 659746-21-1 9,10-bis(1-hydroxymethyl)anthracene-9,10-endoperoxide 
• 103162-56-7 9,10-bis(phenylhydroxymethyl)anthracene 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 
• 589-18-4 4-Methylbenzyl alcohol 

Relevant academic research and scientific papers

A fluorescent bisanthracene macrocycle discriminates between matched and mismatch-containing DNA

The macrocyclic anthracene derivative that binds to matched and mismatched base pairs in DNA by distinct modes was investigated. The macrocycle was readily synthesized by a [2+2]-type cyclocondensation of anthracene-9,10- dicarboxaldehyde with 2,2'-oxybis

Synthesis of anthracene derivatives of 1,3-diazabicyclo[3.1.0]hex-3-ene

Novel mono- and bis-photochromic compounds of 1,3-diazabicyclo[3.1.0]hex-3-enes based on anthracene moiety were synthesized efficiently. Photochromic compounds were synthesized through the reaction of 10-(hydroxymethyl)anthracene-9-carbaldehyde and anthracene-9-carbaldehyde or 9,10-anthracenedicarbaldehyde as bis-aldehydes with ketoaziridines in dry DMF at room temperature. Photochromic compounds exhibited photochromic behavior both in solution and in solid state by irradiation under UV light at 254 nm. Compounds bearing 4-NO2 on aziridine moiety showed intensive color change. Compounds were characterized by IR, 1H NMR, 13C NMR, and UV-Vis.

A highly sensitive and selective visible-light excitable luminescent probe for singlet oxygen based on a dinuclear ruthenium complex

A dinuclear Ru(ii) complex of [(bpy)2Ru(H2ipaip)Ru(bpy)2]Cl4 {bpy = 2,2′-bipyridine, H2ipaip = 2-(9-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)anthracen-10-yl)-1H-imidazo[4,5-f][1,10]phenanthroline} is newly synthesized and characterized. Singlet oxygen sensing and ground- and excited-state acid-base properties of this complex are studied. The results indicated that the complex acted as a highly sensitive and selective luminescent probe for singlet oxygen (1O2) in neutral and alkaline aqueous media under visible light excitation at 458 nm, resulting in 5.2- and 7.6-fold emission enhancement, respectively. This probe has advantages of visible light excitation, low singlet oxygen detection limits of 2.7-3.1 nM and high water solubility, thus holding great potential for applications in biological systems.

Engineering COFs as smart triggers for rapid capture and controlled release of singlet oxygen

Capture and controlled release of singlet oxygen (1O2) are of great significance but very challenging due to its very short lifetime and high reactivity. To address this challenge, we rationally designed and fabricated a highly crystalline, robust, and porous three-dimensional covalent organic framework (3D COF) by installing functional anthracene moieties on its skeleton for1O2related applications. Attributed to its open networks, regular channels, and light skeletal density, the active anthracene sites in the 3D COF can be easily and fully accessed, hence affording superior performance compared with other materials such as 2-dimensional COFs and amorphous polymers. Notably, the 3D COF displays the current record-high1O2capture rate among all reported porous materials, verified by various characterization techniques and rational analysis. Furthermore, we used the 3D COF platform as a stimuli-responsive smart material for anti-fake applications. This study not only provides an outstanding platform for1O2capture and release but also extends the application scope of COFs.

Twofold π-Extension of Polyarenes via Double and Triple Radical Alkyne peri-Annulations: Radical Cascades Converging on the Same Aromatic Core

A versatile synthetic route to distannyl-substituted polyarenes was developed via double radical peri-annulations. The cyclization precursors were equipped with propargylic OMe traceless directing groups (TDGs) for regioselective Sn-radical attack at the triple bonds. The two peri-annulations converge at a variety of polycyclic cores to yield expanded difunctionalized polycyclic aromatic hydrocarbons (PAHs). This approach can be extended to triple peri-annulations, where annulations are coupled with a radical cascade that connects two preexisting aromatic cores via a formal C-H activation step. The installed Bu3Sn groups serve as chemical handles for further functionalization via direct cross-coupling, iodination, or protodestannylation and increase solubility of the products in organic solvents. Photophysical studies reveal that the Bu3Sn-substituted PAHs are moderately fluorescent, and their protodestannylation results in an up to 10-fold fluorescence quantum yield enhancement. DFT calculations identified the most likely possible mechanism of this complex chemical transformation involving two independent peri-cyclizations at the central core.

Organic light-emitting material with anthracene structure and organic light-emitting device with anthracene structure

The invention provides an organic light-emitting material with anthracene structure and an organic light-emitting device with anthracene structure and belongs to the technical field of organic photoelectric materials. The organic light-emitting material with anthracene structure comprises anthracene rings that are a blue light-emitting material parent nucleus structure having excellent performanceand having high triplet state energy level and wide energy gap; by connecting benzimidazole groups to molecules, the material is provided with improved electron transport capacity so that carrier transport is balanced. Compared with the prior art, the organic light-emitting material with anthracene structure applied to organic light-emitting devices, particularly as blue objective material in a light-emitting layer has higher luminous efficiency.

A new approach to polycyclic azaarenes: Visible-light photolysis of vinyl azides in the synthesis of diazabenzopyrene and diazaperylene

Nitrogen containing polycyclic aromatics are attractive π-functional materials due to their stability and interesting electronic and optical properties. As such, new avenues for the incorporation of nitrogen heteroatoms into arenes are desirable. The visible-light photocyclization of vinyl azides is an efficient method to form nitrogen heterocycles, but previously required complex photocatalysts. Herein we report the cyclization of vinyl azide derivatives of anthracene via either thermal activation or visible-light activation without a photocatalyst. The resulting products are two novel azaarenes: 1,8-diazabenzo[e]pyrene and 3,9-diazaperylene. The electrochemical and photophysical properties of the materials are compared to those of their hydrocarbon analogues. Both materials exhibit increased electron affinities and high quantum yields (up to 82%). Successive protonation of the nitrogen heteroatoms first quenches, then fully restores fluorescence at longer wavelengths, indicating possible applications as pH sensors.

A turn-on fluorescent Fe3+ sensor derived from an anthracene-bearing bisdiene macrocycle and its intracellular imaging application

Integrating N2-hydroxyethyldiethylenetriamine with anthracene gives a [2+2] macrocycle fluorescent sensor. This sensor displays an instant/reversible turn-on response specific to Fe3+, which allows facile visualization of the Fe3+/Fe2+ transition and intracellular Fe3+ imaging. the Partner Organisations 2014.

Fluorescent Zn2+ chemosensors, functional in aqueous solution under environmentally relevant conditions

The synthesis and evaluation of two new ratiometric chemosensors for the quantification of potentially toxic free Zn2+ ions in aqueous solutions are described. Both sensors show high selectivity for Zn2+ over other cations, and are functional at environmentally relevant pH with detection limits of 0.05 μM for free Zn2+.

Synthesis and photophysical studies of bis-enediynes as tunable fluorophores

We have synthesized a family of bis-enediynes by two complementary Pd/Cu-catalyzed Sonogashira cross-coupling methods. One is a modified Sonogashira reaction between the TMS-protected tetraalkyne 20 (or 21) and various aromatic bromides to afford bis-enediynes 22a-d and 23a-d bearing different peripheral aryl units. The other, the reaction of bifunctional 1,1-dibromo-1-alkenes with phenylacetylene, afforded a series of bis-enediynes 24-32 bearing various core aryl groups. These chemical modifications to the core and periphery of bis-enediynes induce dramatic changes in absorption and emission spectra. Bis-enediynes 22 and 23 show a large Stokes shift of about 50-110 nm when compared to the less-conjugated bis-enediynes 20 and 21. Absorptions and emissions of bis-enediynes 25, 27-29, and 31 were red-shifted relative to those of enediyne 35. Substantial increases in fluorescence quantum yields are observed as a result of extending the π-conjugation. The emission wavelength of bis-enediynes was tailored from indigo blue to reddish-orange, suggesting that the color of emission can be tunable by modification of the core and/or peripheral units.