9,10-Bis(phenylethynyl)anthracene

Base Information

• Chemical Name: 9,10-Bis(phenylethynyl)anthracene
• CAS No.: 10075-85-1
• Molecular Formula: C30H18
• Molecular Weight: 378.473
• Hs Code.: 29029090
• European Community (EC) Number: 233-210-8
• UNII: FC8JDB70DQ
• DSSTox Substance ID: DTXSID3064936
• Nikkaji Number: J236.270H
• Wikipedia: 9,10-Bis(phenylethynyl)anthracene
• Wikidata: Q274980
• Metabolomics Workbench ID: 57833
• Mol file: 10075-85-1.mol

Synonyms:9,10-bis(phenylethynyl)anthracene;BPEA cpd

Chemical Property of 9,10-Bis(phenylethynyl)anthracene

Chemical Property:

• Appearance/Colour: orange crystalline powder
• Vapor Pressure: 2.3E-14mmHg at 25°C
• Melting Point: 252-258 °C
• Refractive Index: 1.753
• Boiling Point: 614.3 °C at 760 mmHg
• Flash Point: 325.6 °C
• PSA: 0.00000
• Density: 1.23 g/cm³
• LogP: 6.79260
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Water Solubility.: It is insoluble in water but is soluble in most organic solvents such as carbon disulfide, alcohols, benzene, chloroform, and hy
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 4
• Exact Mass: 378.140850574
• Heavy Atom Count: 30
• Complexity: 605

Purity/Quality:

99% ^*data from raw suppliers

9,10-Bis(phenylethynyl)anthracene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C#CC2=C3C=CC=CC3=C(C4=CC=CC=C42)C#CC5=CC=CC=C5
• General Description: 9,10-Bis(phenylethynyl)anthracene (PEAnt) is a fluorescent dye that typically exhibits quenching upon aggregation, as demonstrated by its derivative in the study. Unlike AIEE-active compounds, its fluorescence diminishes when aggregated in aqueous environments, highlighting its contrasting behavior to systems showing emission enhancement in the condensed phase. This property makes it a reference for studying aggregation-induced quenching effects in comparison to AIEE-active dyes.

Technology Process of 9,10-Bis(phenylethynyl)anthracene

There total 26 articles about 9,10-Bis(phenylethynyl)anthracene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

9,10-Dibromoanthracene (523-27-3) + phenylacetylene (536-74-3) → 9,10-diphenylethynylanthracene (10075-85-1)

Guidance literature:

With triethylamine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 89 ℃; for 3h;

DOI:10.1246/bcsj.57.752

Reference yield: 99.0%

9,10-bis(phenylethynyl)-9,10-dihydro-9,10-epidioxidoanthracene (32287-35-7) → 9,10-diphenylethynylanthracene (10075-85-1)

Guidance literature:

In chloroform-d1; at 20 ℃; for 1.5h;

DOI:10.1002/poc.3607

Reference yield: 98.0%

Benzyl phenyl sulfone (3112-88-7) + 10-(phenylethynyl)-9-anthracenecarbaldehyde → 9,10-diphenylethynylanthracene (10075-85-1)

Guidance literature:

With diethyl chlorophosphate; lithium hexamethyldisilazane; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1055/s-0032-1316867

upstream raw materials:

9,10-bis(phenylethynyl)-9,10-dihydroanthracene-9,10-diol

9-(α,β-dichloro-styryl)-10-phenylethynyl-anthracene

9,10-Dibromoanthracene

Bis(phenylethynyl)magnesium

Downstream raw materials:

9,10-bis(phenylacetyl)anthracene

9-phenylacetyl-10-(phenylethynyl)anthracene

(E,E)-9,10-Bis(styryl)anthracene

9-cis-styryl-10-trans-anthracene

Refernces

Self-assembly of amphiphilic fluorescent dyes showing aggregate-induced enhanced emission: Temperature dependence of molecular alignment and intermolecular interaction in aqueous environment

10.1039/b910531j

The study investigates the self-assembly and fluorescence properties of two amphiphilic dye derivatives, 9,10-bis(phenylethynyl)anthracene (PEAnt) derivative 1 and cyano-bis(biphenyl)ethene (CNBE) derivative 2, both having hexaethylene glycol (Hxg) groups as side chains. PEAnt derivative 1 serves as a typical fluorescent dye that experiences quenching upon aggregation, while CNBE derivative 2 exhibits aggregate-induced enhanced emission (AIEE) properties. The researchers explored how these compounds self-assemble in water and how their fluorescence changes with temperature. They found that compound 2 shows significant fluorescence enhancement and a red shift in emission wavelength when aggregated in water, and its AIEE behavior is more sensitive to temperature changes than the exciton interaction, making it a potential probe for detecting microscopic environmental changes.