159-68-2

Basic information

• Product Name: 5,5'-spirobi[dibenzo[b,d]silole]
• Synonyms: 5,5'-spirobi[dibenzo[b,d]silole];9,9'-Spirobi[9H-9-silafluorene];5,5'-spirobi[benzo[b][1]benzosilole];9,9'-Spirobi[9H-9-silafluorene]
• CAS NO: 159-68-2
• Molecular Formula: C24H16Si
• Molecular Weight: 332.46934
• EINECS: -0
• Mol File: 159-68-2.mol
• Article Data: 6

Chemical Properties

• Melting Point: 230.0 to 234.0 °C
• Boiling Point: 460°C(lit.)
• Flash Point: 237.9°C
• Appearance: /
• Density: 1.25g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 5,5'-spirobi[dibenzo[b,d]silole](CAS DataBase Reference)
• NIST Chemistry Reference: 5,5'-spirobi[dibenzo[b,d]silole](159-68-2)
• EPA Substance Registry System: 5,5'-spirobi[dibenzo[b,d]silole](159-68-2)

Safety Data

• Hazardous Substances Data: 159-68-2(Hazardous Substances Data)

Usage

General Description

5,5'-spirobi[dibenzo[b,d]silole] is a chemical compound with a unique spirocyclic structure consisting of two dibenzo[b,d]silole units connected at their 5th position. It belongs to the family of siloles, which are organic compounds with a silicon atom and a five-membered ring. 5,5'-spirobi[dibenzo[b,d]silole] has gained attention for its potential applications in organic electronics, optoelectronic devices, and materials science due to its high thermal stability, strong luminescent properties, and good charge transport abilities. It is often used as a building block for creating novel materials with specific electronic and optical properties, and its unique structure and properties make it a promising candidate for various technological applications. Further research and development of 5,5'-spirobi[dibenzo[b,d]silole] may lead to the creation of advanced materials for future technology.

Upstream product

• 2052-07-5 2-Bromobiphenyl 
• 1426051-47-9 di[2-(1,1'-biphenyl)]silane 
• 13029-09-9 2,2'-dibromobiphenyl 
• 583-53-9 2,3-dibromobenzene 
• 16291-32-0 biphenyl-2,2'-diyl-bis-lithium 
• 75-79-6 Methyltrichlorosilane 
• 18090-00-1 9-chloro-9-methyl-9-silafluorene 

Downstream Products

• 92-52-4 biphenyl 
• 18866-41-6 5-biphenyl-2-yl-5-phenyl-5H-dibenzosilole 

Relevant articles and documents

Infrared and Raman spectroscopy of 9,9′-spirobifluorene, bis(2,2′-biphenylene)silane, and bis(2,2′-biphenylene)germane. Vibrational assignment by depolarization measurement and HF and density functional theory studies

The infrared and Raman spectra of 9,9′-spirobifluorene (SBFL), bis(2,2′-biphenylene)silane (BBPS), and bis-(2,2′-biphenylene)germane (BBPG) are measured, and the vibrational frequencies and modes for these molecules are assigned by ab initio Hartree-Fock and Becke 3-Lee-Yang-Parr (B3LYP) density functional theory (DFT) calculations using the 4-31G and 3-21G basis sets for SBFL and for BBPS and BBPG, respectively. Assignment of some of the vibrational modes of SBFL is also confirmed by solution Raman spectroscopy with the depolarization method. Comparison of the calculated and experimental vibrational spectra reveals that the DFT calculations are quite accurate in predicting the vibrational frequencies, intensities, and modes. It is found that the central Si and Ge atoms dominantly enhance some of the IR intensities of the vibrations involving only the M-C4 (M = Si, Ge) antisymmetric stretching motion. The enhancement of some of the infrared intensities is accounted for by the increase of the electric dipole moment involving the M-C4 vibrations due to the presence of the small electronegative Si and Ge atoms in the central position.

Construction method of organic phase electrochemical luminescence system of rigid spiro silole compound

The invention discloses a construction method of an organic phase electrochemical luminescence system of a rigid spiro silole compound. The method comprises the following steps: dissolving an electrochemical luminescence reagent 5,5'-spiro bis[dibenzo[b,d]silole] and a supporting electrolyte tetrabutyl ammonium hexafluorophosphate in an acetonitrile flushing solution, taking a glassy carbon electrode as a working electrode, taking a platinum electrode and a silver wire electrode as a counter electrode and a reference electrode, immersing into the obtained organic phase, and removing the oxygen in the organic phase to obtain the electrode. According to the invention, the electrochemical luminescence system is easy to construct, the surface of an electrode does not need to be coated with a luminescence agent, the dosage of the used luminescence agent is small, a co-reactant is not needed, generated ECL signals are strong, and the stability and reproducibility are good; and compared with the traditional silole such as hexaphenyl silole, the luminescent molecule has the advantages that the ECL emission of 5,5'-spirobis[dibenzo[b,d]silole] in an acetonitrile solution is enhanced by about 6 times, and the luminous efficiency and the sensitivity are obviously improved.

Rhodium-catalyzed asymmetric synthesis of spirosilabifluorene derivatives

Si goes chiral: Treatment of a bis(biphenyl)silane with a catalytic amount of a rhodium complex gave a spirosilabifluorene bearing a quaternary silicon atom. By using a rhodium catalyst with a chiral phosphine ligand (see scheme), asymmetric dehydrogenative cyclization proceeded to give chiral derivatives in good yields and enantioselectivities. Copyright