7385-10-6

Usage

Uses

Used in Organic Synthesis:
9-(TRIMETHYLSILYL)FLUORENE is used as a building block for the synthesis of various functionalized fluorene derivatives. Its presence in these compounds contributes to the development of new materials with tailored properties for specific applications.
Used in Electronic Devices:
In the Electronics Industry, 9-(TRIMETHYLSILYL)FLUORENE is used as a component in the production of light-emitting materials and organic semiconductors. Its role in these materials is crucial for the performance of devices such as organic light-emitting diodes (OLEDs) and solar cells, where its electronic and optical characteristics enhance device efficiency and functionality.
Used in Materials Science:
9-(TRIMETHYLSILYL)FLUORENE also finds applications in the field of materials science, where its unique properties are harnessed to create advanced materials with improved performance in various settings. Its potential in this area is a result of ongoing research and development efforts to explore new uses for this versatile compound.

InChI:InChI=1/C16H18Si/c1-17(2,3)16-14-10-6-4-8-12(14)13-9-5-7-11-15(13)16/h4-11,16H,1-3H3

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 881-04-9 9H-fluoren-9-yllithium 
• 3531-83-7 fluorenylsodium 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 2052-07-5 2-Bromobiphenyl 
• 86-73-7 9H-fluorene 
• 88223-08-9 C₁₆H₁₇CsSi 
• 75191-00-3 9-(trimethylsilyl)-9-fluorenyllithium 

Downstream Products

• 7351-45-3 9,9'-bis(trimethylsilyl)fluorene 
• 80077-84-5 9-[bis(4-methylphenyl)methylene]-9H-fluorene 
• 1066-40-6 Trimethylsilanol 
• 1836-87-9 9-Benzylidene-9H-fluorene 
• 56954-91-7 (9H-fluoren-9-yl)(phenyl)methanol 
• 872053-63-9 9-(di(m-tolyl)methylene)-9H-fluorene 
• 53973-93-6 Dimethylphenylsilyl-(9-trimethylsilyl-9-fluorenyl)-ether 
• 53973-95-8 (9-Dimethylphenylsilyl-9-fluorenyl)-trimethylsilyl-ether 
• 87463-61-4 fluorenethione S-(2,4,6-tri-tert-butylphenyl)imide 
• 88534-40-1 9-[bis(4-methoxyphenyl)methylidene]-9H-fluorene 
• 746-47-4 tetrabenzo[5.5]fulvalene 
• 96258-43-4 2-(p-phenylphenyl)-3,3-(2,2'-biphenyldiyl)-2-propene 
• 26356-44-5 5-((9H-fluoren-9-ylidene)methyl)benzo[d][1,3]dioxole 
• 843638-98-2 2-((9H-fluorene-9-ylidene)methyl)thiophene 

Relevant academic research and scientific papers

9-Silyl(-Germyl,-Stannyl) Substituted Derivatives of 1-(9-Fluorenyl)-germatranes. Synthesis, Characterisation, and Crystal Structures

9-Trimethylsilyl- and 9-trimethylgermyl substituted derivatives of 1-(9-fluorenyl)germatranes C13H8(R)Ge(OCH2CH2)3N (1 - 3) (1: R = H; 2: R = Me3Si; 3: R = Me3Ge) were prepared by the reaction of 9-tribromogermyl derivatives of fluorene C13H8(R)GeBr3 (4 - 6) with N(CH2CH2OSnAlk3)3 (7: Alk = Et; 8: Alk = Bu). 1-(9-Trimethylstannyl-9-fluorenyl)germatrane (14) was synthesised by the reaction of the germatrane (1) with Me3SnNMe2. Formulas and structures were established by elemental analyses, (1H, 13C) NMR spectroscopy and mass spectrometry; crystal structures of 2 and 14 are reported.

Carbo-quinoids: Stability and reversible redox-proaromatic character towards carbo-benzenes

The carbo-mer of the para-quinodimethane core is stable within in a bis(9-fluorenylidene) derivative. Oxidation of this carbo-quinoid with MnO2 in the presence of SnCl2and ethanol affords the corresponding p-bis(9-ethoxy-fluoren-9-yl

METHOD FOR PRODUCING ORGANOSILICON COMPOUND USING HALOSILANE AS RAW MATERIAL

PROBLEM TO BE SOLVED: To provide a novel method for producing an organosilicon compound. SOLUTION: The method for producing an organosilicon compound includes a reaction step (I) of reacting a halosilane represented by formula (a) with a compound containing a hydrocarbon group represented by formula (b) in the presence of an organic base to generate an organosilicon compound represented by formula (c). (In the formula (I), n is an integer of 0-3; each R1 independently represents a hydrogen atom or a C1-20 hydrocarbon group which may contain a heteroatom; X represents a bromo group (-Br) or a chloro group (-Cl); and R2 represents a compound containing a hydrocarbon group.) SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2020,JPOandINPIT

Migratory Insertion of Carbenes into Au(III)-C Bonds

Migratory insertion of carbon-based species into transition-metal-carbon bonds is a mechanistic manifold of vast significance: it underlies the Fischer-Tropsch process, Mizoroki-Heck reaction, Ziegler-Natta and analogous late-transition-metal-catalyzed olefin polymerizations, and a number of carbonylative methods for the synthesis of ketones and esters, among others. Although this type of reactivity is well-precedented for most transition metals, gold constitutes a notable exception, with virtually no well-characterized examples known to date. Yet, the complementary reactivity of gold to numerous other transition metals would offer new synthetic opportunities for migratory insertion of carbon-based species into gold-carbon bonds. Here we report the discovery of well-defined Au(III) complexes that participate in rapid migratory insertion of carbenes derived from silyl- or carbonyl-stabilized diazoalkanes into Au-C bonds at temperatures ≥ -40 °C. Through a combined theoretical and experimental approach, key kinetic, thermodynamic, and structural details of this reaction manifold were elucidated. This study paves the way for homogeneous gold-catalyzed processes incorporating carbene migratory insertion steps.

Palladium-Catalyzed Formal [4 + 1] Annulation via Metal Carbene Migratory Insertion and C(sp2)-H Bond Functionalization

A highly efficient and operationally simple palladium-catalyzed formal [4 + 1] annulation reaction has been developed. The reaction is featured by the formation of two different C-C bonds on a carbenic center. It represents a concise method for the synthesis of a wide range of polycyclic aromatic hydrocarbons (PAHs) and 1H-indenes with easily available (trimethylsilyl)diazomethane as the carbene source. Metal carbene migratory insertion and C(sp2)-H bond activation are proposed as the key steps in this transformation. The reaction further demonstrates the versatility of the carbene-based coupling in combination with various transition-metal-catalyzed transformations.

Peterson olefination: Unexpected rearrangement in the overcrowded polycyclic aromatic ene series

An attempted synthesis of the angularly annelated 9-(11′-benzo[a] fluoren-11′-ylidene)-9H-fluorene (3) through a Peterson olefination reaction between (9H-fluoren-9-yl)trimethylsilyl anion (5a) and 11H-benzo[a]fluoren-11-one (6) led to the linearly annelated 9-(11′-benzo[b]fluoren-11′-ylidene)-9H-fluorene (4), due to an unexpected rearrangement. The proposed mechanism of the rearrangement is illustrated. The core of the mechanism is an intramolecular Haller-Bauer cleavage of the naphthyl C11a′-C11′ bond in the β-oxysilane anion 11 (formed from 5a and 6) to give the 1-naphthyl anion (E)-12, followed by E/Z isomerization to (Z)-12 and by proton migration to give the 3-naphthyl anion (Z)-14. The intramolecular nucleophilic addition of the naphthyl anion at C-3′ of (Z)-14 to the carbonyl carbon gives the β-oxysilane anion 15, a benzo[b]fluorenylidene derivative. The mechanism is supported by the results of DFT calculations. The synthesis of 3 was achieved by application of Barton's double extrusion diazo-thione coupling method.

Antiaromatic spacer-bridged bisfluorenyl dications generated by superacid induced ionization

Derivatives of the dication of tetrabenzo[5.5]fulvalene were prepared with phenyl and ethynyl spacers through ionization of the appropriate bis-methylethers. The antiaromaticity shown by the parent dication was demonstrated for these dications with spacer

Dications of fluorenylidenes. The relationship between redox potentials and antiaromaticity for meta- and para-substituted diphenylmethylidenefluorenes

Electrochemical oxidation of meta-substituted diphenylmethylidenefluorenes (3a-g) results in the formation of fluorenylidene dications that are shown to be antiaromatic through calculation of the nucleus independent chemical shift (NICS) for the 5- and 6-

Crystal, molecular, and electronic structure of 9,9′-bis(trimethylsilyl)fluorene

The crystal and molecular structure of 9,9′-bis(trimethylsilyl)fluorene (1) has been determined by X-ray diffraction. The crystal of (1) is orthorhombic, space group Pnma with unit cell dimensions: a = 16.906(2) ?, b = 13.8080(10) ?, c = 8.1690(10) ?, α = β = γ = 90°. The silicon atoms are in a slightly distorted tetrahedral environment with C-Si-C bond angles in the range 107.13°-112.49°. A notable feature of the molecular structure is the significant deviation of the Sil-C9-Si2 angle (118.9°) from the normal tetrahedral value. This behaviour is attributed mainly to some intramolecular CH...π interactions.

Dications of Fluorenylidenes. Electronic Effects on the Paratropicity/Antiaromaticity of 2,7-Disubstituted Fluorenyl Cations

Oxidation of 2,7-disubstituted tetrabenzo[5.5]fulvalene derivatives 1a-d resulted in the formation of dications which are fluorenyl cations linked by a single bond. These fluorenyl cations exhibit significant paratropicity in the 1H NMR spectrum, which is attributed to an antiaromatic ring current. Interaction of the perpendicular ring systems is evident in the upfield shift of carbons a and a', presumably due to σ-p donation. The lack of variation in the upfield shift of carbons a and a', compared to previously reported systems, is attributed to the similarities of the geometries of 1a-d2+. Substitution at a remote site affects the antiaromaticity of the unsubstituted fluorenyl cation, but the nature of the effect of the substituent is not understood. Direct substitution on the fluorenyl cation by substituents which increase electron density, either through inductive π polarization or through resonance, cause a paratropic shift in the probe proton.