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

Description

1,1,2,3,4,5-Hexaphenylsilole (HPS) is an aggregation-induced emission (AIE) material characterized by its unique property of enhanced fluorescence in the aggregated state. It is derived from the photolysis and thermolysis of 1,4,5,6,7,7-hexaphenyl-7-silabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic anhydride (XIb) and is known for its potential applications in various fields due to its distinct chemical and optical properties.

Uses

Used in Organic Chemistry:
1,1,2,3,4,5-Hexaphenylsilole is used as a reactant in organic synthesis for the formation of bicyclosilaheptene through π4s+π2s cycloaddition with ethyl acrylate. This reaction demonstrates the versatility of HPS in creating complex molecular structures and its potential use in the development of novel compounds.
Used in OLED Emitting Layer:
1,1,2,3,4,5-Hexaphenylsilole is used as an AIE material in the OLED (Organic Light-Emitting Diode) emitting layer for its ability to enhance fluorescence in aggregated states. This property makes it a valuable component in the design and fabrication of OLEDs, contributing to improved device performance and efficiency.
Used in Material Science:
1,1,2,3,4,5-Hexaphenylsilole is used as a component in the development of advanced materials due to its unique aggregation-induced emission properties. Its incorporation into various materials can lead to the creation of novel materials with enhanced optical and electronic properties, applicable in a wide range of industries, including electronics, photonics, and sensing technologies.
Used in Chemical Research:
1,1,2,3,4,5-Hexaphenylsilole is used as a model compound in chemical research to study the behavior of AIE materials and their interactions with other molecules. This research can provide valuable insights into the design and synthesis of new materials with tailored properties for specific applications.

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