752-28-3

Basic information

• Product Name: 1,1,2,3,4,5-Hexaphenylsilole
• Synonyms: 1,1,2,3,4,5-Hexaphenylsilole;1,1,2,3,4,5-Hexaphenyl-1H-silole;Silacyclopenta-2,4-diene, 1,1,2,3,4,5-hexaphenyl-;1,1,2,3,4,5-hexakis-phenylsilole
• CAS NO: 752-28-3
• Molecular Formula: C₄₀H₃₀Si
• Molecular Weight: 538.7517
• Mol File: 752-28-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 193.0 to 197.0 °C
• Boiling Point: 674.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 1,1,2,3,4,5-Hexaphenylsilole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1,2,3,4,5-Hexaphenylsilole(752-28-3)
• EPA Substance Registry System: 1,1,2,3,4,5-Hexaphenylsilole(752-28-3)

Safety Data

• Hazardous Substances Data: 752-28-3(Hazardous Substances Data)

Usage

Uses

Hexaphenylsilacyclopentadiene may undergo π4s+π2s cycloaddition with ethyl acrylate to form bicyclosilaheptene. The same study reports similar cycloaddition reactions with various dienophiles. The reaction of hexaphenylsilacyclopentadiene with perbenzoic acid yields a mixture of tetraphenylfuran and cis-dibenzoylstilbene.

General Description

HPS is an aggregation-induced emission (AIE) material for use in the OLED emitting layer. Photolysis and thermolysis of 1,4,5,6,7,7-hexaphenyl-7-silabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (XIb) may lead to the formation of hexaphenylsilacyclopentadiene.

Upstream product

• 501-65-5 diphenyl acetylene 
• 80-10-4 diphenylsilyl dichloride 
• 16030-07-2 1-chloro-1,2,3,4,5-pentaphenyl-1-silacyclopentadiene 
• 74-88-4 methyl iodide 
• 21289-08-7 1,4-dilithio-1,2,3,4-tetraphenylbutadiene 

Downstream Products

• 1065-76-5 1,4,5,6,7,7-hexaphenyl-7-sila-bicyclo[2.2.1]hept-5-ene-2endo,3endo-dicarboxylic acid anhydride 
• 1762-11-4 1,2,3,4,9,9-hexaphenyl-1,4-dihydro-1,4-episilano-naphthalene 
• 51528-44-0 1,4,5,6,7,7-hexaphenyl-7-sila-bicyclo[2.2.1]hept-5-ene-2endo-carbonitrile 
• 1184-27-6 1,4,5,6,7,7-hexaphenyl-7-sila-bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylic acid dimethyl ester 
• 51528-50-8 C,C'-diphenyl-C,C'-(1,4,5,6,7,7-hexaphenyl-7-sila-bicyclo[2.2.1]hepta-2,5-diene-2,3-diyl)-bis-methanone 
• 51528-40-6 1,4,5,6,7,7-hexaphenyl-7-sila-bicyclo[2.2.1]hept-5-ene-2endo-carboxylic acid ethyl ester 
• 752-67-0 1,1,2,3,4,4,5,6-octaphenyl-1,4-dihydro-[1,4]disiline 

Relevant articles and documents

Reduction of 1-chloro-1,2,3,4,5-pentaphenylsilole: Formation of silole monoanion and dianion

The reduction of 1-chloro-1,2,3,4,5-pentaphenylsilole, (C4Ph4SiPhCl, 1) with 2 equiv lithium gave the pentaphenylsilole anion [C4Ph4SiPh]- (2), silole dianion [C4Ph4Si]2-/s

Blue-shifted aggregation-induced emission of siloles by simple structural modification and their application as nitro explosive chemosensors

To induce blue-shifted emission of siloles, two tolyl-substituted derivatives-1,1-diphenyl-2,3,4,5-tetra(m-tolyl)-1H-silole (m-TS) and 1,1-diphenyl-2,3,4,5-tetra(o-tolyl)-1H-silole (o-TS)-were prepared, and their photophysical properties were compared with those of a reference compound, hexaphenylsilole (HPS). By substituting methyl groups at ortho positions of peripheral tetraphenyl rings on the silacyclopentadiene ring, intramolecular rotations could be successfully controlled and the photophysical properties were varied, while substituting methyl groups at meta positions showed similar photophysical properties compared with the case of HPS. That is, simple structural modification at the ortho position significantly affects the geometry and the photophysical properties of silole, which leads to blue-shifted emission. Finally, two tolyl-substituted siloles and HPS were employed as chemosensors for the detection of nitro explosives, and o-TS showed the highest sensing ability.

Efficient blue emission from siloles

2,3,4,5-Tetraphenylsiloles with different 1,1-substituents on the ring silicon atoms, i.e., 1,1-dimethyl-2,3,4,5-tetraphenylsilole (1), 1-methyl-l-(3-chloropropyl)-2,3,4,5-tetraphenylsilole (2), 1-methyl-l,2,3,4,5-pentaphenylsilole (3) and hexaphenylsilol