79628-06-1

Usage

Chemical Family

Silole family

Silicon Content

Contains silicon

Trimethylsilyl Groups

Two trimethylsilyl groups attached to the silicon atom

Phenyl Groups

Two phenyl groups attached to the carbon atoms

Methyl Groups

Two methyl groups attached to the carbon atoms

Potential Applications

Organic electronics, optoelectronics, and materials science

Electronic and Optical Properties

Unique electronic and optical properties

Synthesis Utility

Can be used as a building block for the synthesis of more complex silicon-containing compounds

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 2170-08-3 dimethylbis(phenylethynyl)silane 
• 160319-30-2 2,5-dilithium-3,4-diphenyl-1,1-dimethylsilole 
• 61851-11-4 1,1-dimethyl-2-phenyl-3-trimethylsilanyl-1H-silirene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 917-54-4 methyllithium 

Relevant academic research and scientific papers

The Combination of Cross-Hyperconjugation and σ-Conjugation in 2,5-Oligosilanyl Substituted Siloles

Reaction of a 2,5-dilithiated silole with excess dichlorodimethylsilane gives the respective 2,5-bis(chlorodimethylsilyl) substituted silole. This compound can be converted to 2,5-bis(oligosilanyl) substituted siloles by addition of a suitable oligosilani

Electrochemiluminescence Platforms Based on Small Water-Insoluble Organic Molecules for Ultrasensitive Aqueous-Phase Detection

Highly efficient detection in the aqueous phase for water-insoluble organic molecule probes is challenging. The bright aggregated-state electrochemiluminescence (ECL) of 1,1-disubstituted 2,3,4,5-tetraphenylsiloles by a co-reactant approach was discovered

Lithio siloles: Facile synthesis and applications

Lithio siloles of diversified structures and substitution patterns were highly efficiently formed from readily available silyl 1,4-dilithio-1,3-butadienes via novel intramolecular skeletal rearrangements. Copyright

2,5-reactive substituent group-containing siloles, silole polycondensates and preparation thereof

2,5-Reactive substituent group-containing siloles of the following general formula are provided STR1 wherein R1 to R4 may be the same or different and independently represent a monovalent hydrocarbon group having from 1 to 12 carbon atoms or a hydrogen atom, and R5 and R6 may be the same or different and independently represent a group selected from monovalent hydrocarbon-substituted sulfur, selenium, silicon, germanium, tin and phosphorus, or a halogen atom. Polycondensates of the siloles and processes for preparing the siloles and polycondensates are described.

Oligosiloles: First synthesis based on a novel endo-endo mode intramolecular reductive cyclization of diethynylsilanes

A general and versatile synthesis of 2,5-difunctional siloles and their conversion into oligosiloles are described. Diethynylsilanes undergo intramolecular reductive cyclization in an endo-endo mode upon treatment with lithium naphthalenide to form 2,5-dilithiosiloles. The 2,5-dilithiosiloles are converted into various 2,5-difunctional siloles by treatment with electrophiles. The resulting 2,5-dibromosilole is further converted into several highly functionalized siloles via palladium-catalyzed cross-coupling reaction or selective mono-lithiation using n-butyllithium in ether. Oligosiloles, from bisiloles to quatersilole, are prepared from certain functional siloles. Oxidative coupling of 2,5-dilithiosilole by use of an Fe(III) complex affords 2,2′-bisilole as yellow crystals. Difunctional oligosiloles, 5,5′-dibromo-2,2′-bisilole and 5,5?-dibromo-2,2′:5′,2″:5″,2? -quatersilole, are prepared by oxidative coupling via higher order cyanocuprate of 2-bromo-5-lithiosilole and 5-bromo-5′-lithio-2,2′-bisilole, respectively. X-ray crystal structures of these bisiloles show highly twisted arrangements between two silole rings with 62-64° of torsion angle. 1H NMR studies on bisiloles show a rapid equilibration between non-coplanar conformers in solution. In UV-visible spectra, nevertheless, all of the oligosiloles have unusually long absorption maxima.

CHEMISTRY OF SILOLES. THE REACTIONS OF SILOLES WITH ORGANOLITHIUM REAGENTS

The chemical behaviour of siloles toward various organolithium reagents in THF has been investigated.The reaction of 1-methyl-1-(trimethylsilyl)-, 1-phenyl-1-(trimethylsilyl)- and 1,1-bis(trimethylsilyl)dibenzosilole(I, II and III) with a large excess of an alkyllithium such as methyllithium or butyllithium afforded 1,1-dialkyldibenzosiloles in quantitative yields.Treatment of I with an excess of phenyllithium gave a mixture of 1-methyl-1-phenyl- and 1,1-diphenyldibenzosilole quantitatively, while with an excess of tert-butyllithium, I afforded 1,1-dimethyl and 1-tert-butyl-1-methyldibenzosilole in low yield.Similar treatment of I and II with 1 equiv. of methyl- or butyl-lithium yielded a mixture of the corresponding mono- and dialkyl-substituted dibenzosiloles. 1-Methyl-3,4-diphenyl-1,2,5-tris(trimethylsilyl)silole reacted with methyllithium in THF to give 1,1-dimethyl-3,4-diphenyl-2,2,5-tris(trimethylsilyl)silole.Similarly, both 2,4-diphenyl-1,1,3,5-tetrakis(trimethylsilyl)silole and 4,5-diphenyl-1,1,2,3-tetrakis(trimethylsilyl)silole with methyllithium afforded two isomers of 1-methyl-2,4-diphenyl-1,2,3,5-tetrakis(trimethylsilyl)-1-silacyclopent-3-ene in a ratio of 3:2 in high yields.

NICKEL-CATALYZED REACTION OF SILACYCLOPROPENES WITH ACETYLENES. A CONVENIENT ROUTE TO 1-SILACYCLOPENTA-2,4-DIENES

The reaction of 1-silacyclopropenes prepared photochemically from phenylethynyldisilanes with acetylenes in the presence of a nickel catalyst has been investigated.The reaction of 1,1-dimethyl-2-phenyl-3-trimethylsilyl-, 1,1-dimethyl-2-phenyl-3-phenyldimethylsilyl-, 1-methyl-1,2-diphenyl-3-trimethylsilyl-, 1,1,2-triphenyl-3-trimethylsilyl- and 1-methyl-1-mesityl-2-phenyl-3-trimethyl-silyl-1-silacyclopropene with a phenylsilylacetylene in the presence of NiCl2(PEt3)2 afforded the respective 2,5-bis(silyl)-3,4-diphenyl-1-silacyclopenta-2,4-dienes in high yields. 1-Methyl-1,3-bis(trimethylsilyl)-2-phenyl-1-silacyclopropene reacted with phenyl(trimethylsilyl)acetylene to give 1-methyl-1,2,5-tris(trimethylsilyl)-3,4-diphenyl-1-silacyclopenta-2,4-diene and isomers, while 1,1-dimesityl-2-phenyl-3-trimethylsilyl-1-silacyclopropene afforded no 1-silacyclopenta-2,4-diene.

UNEXPECTED BEHAVIOR OF SILOLES TOWARD ORGANOLITHIUM REAGENTS

The reaction of 5-trimethylsilyl-5-methyldibenzosilole (I) with an excess of methyllithium in THF afforded 5,5-dimethyldibenzosilole (II) in quantitative yield.Treatment of I with an excess of butyllithium gave 5,5-dibutyldibenzosilole (III) quantitatively.Similar treatment of II with butyllithium in THF at room temperature gave III in almost quantitative yield, while treatment of III with methyllithium at reflux temperature gave II and 5-butyl-5-methyldibenzosilole in 10 and 40percent yield, in addition to 37percent of the starting III. 1,2,5-Tris(trimethylsilyl)-1-methyl-3,4-diphenylsilole also reacted with methyllithium to give 1,1-dimethyl-2,2,5-tris(trimethylsilyl)-3,4-diphenyl-1-silacyclopent-3-ene and 1,1-dimethyl-2,5-bis(trimethylsilyl)-3,4-diphenylsilole in 70 and 7percent yield.A five-coordinate silicon compound is proposed as an intermediate.