171408-84-7

Basic information

• Product Name: 2,7-Dibromo-9,9'-spiro-bifluorene
• Synonyms: 2,7-DIBROMO-9,9'-SPIROBIFLUORENE;9,9′-Spirobi[9H-fluorene],2,7-dibromo;2,7-DIBROMO-9,9''-SPIRO-BIFLUOROENE;2,7-Dibromo-9,9-spriobifluorene;2,7-Dibromo-9,9'-sp;2,7-DibroMo-9,9'-spirobi[9H-fluorene];2,7-dibroMo-9,9'-Spirobi[9H]-fluorene (DBSBF);2,7-dibroMo -9,9-screwtwo fluorene
• CAS NO: 171408-84-7
• Molecular Formula: C₂₅H₁₄Br₂
• Molecular Weight: 474.19
• EINECS: 1312995-182-4
• Product Categories: Fluorene Derivatives;Fluorene Series
• Mol File: 171408-84-7.mol
• Article Data: 23

Chemical Properties

• Melting Point: 334-336°C
• Boiling Point: 557.435 °C at 760 mmHg
• Flash Point: 335.129 °C
• Appearance: off-white crystal
• Density: 1.74 g/cm³
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 2,7-Dibromo-9,9'-spiro-bifluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-Dibromo-9,9'-spiro-bifluorene(171408-84-7)
• EPA Substance Registry System: 2,7-Dibromo-9,9'-spiro-bifluorene(171408-84-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 171408-84-7(Hazardous Substances Data)

Usage

Chemical Properties

white powder

Uses

2,7-Dibromo-9,9′-spirobifluorene can be used in the preparation of 9,9′-spirobifluorene-based small molecules, which can further be utilized as host materials in organic light emitting diodes (OLEDs).

General Description

2,7-Dibromo-9,9′-spirobifluorene is a 9,9 substituted poly(2,7-fluorene) that is synthesized from 2,7-dribromo-9-fluorenone by reacting with a Grignard reagent of 2-bromobiphenyl. It has high photoluminescence and electroluminescent quantum efficiency that make it useful in the development of organic electronic devices.

Upstream product

• 2052-07-5 2-Bromobiphenyl 
• 6344-61-2 9H-fluoren-1-ol 
• 14348-75-5 2,7-dibromofluorene-9-one 
• 583-53-9 2,3-dibromobenzene 
• 98-80-6 phenylboronic acid 
• 159-66-0 9,9'-spirobifluorene 
• 100-58-3 phenylmagnesium bromide 
• 82214-69-5 2-biphenylmagnesium bromide 
• 486-25-9 9-fluorenone 
• 90-41-5 2-phenylaniline 
• 2113-51-1 2-iodobiphenyl 
• 16433-88-8 2,7-dibromo-9H-fluorene 
• 86-00-0 2-nitrobiphenyl 
• 86-73-7 9H-fluorene 

Downstream Products

• 728911-52-2 2,7-bis (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9′-spirobi[9H-fluorene] 
• 1206885-07-5 2,7-bis(4'-cyanophenyl)-9,9'-spirobifluorene 
• 1206885-08-6 2',7'-dibromo-2,7-bis(4'-cyanophenyl)-9,9'-spirobifluorene 
• 1158844-71-3 C₃₁H₁₈Br₂ 
• 1158844-74-6 2,7-bis-(4-bromophen-1-yl)-9,9’-spirobifluorene 
• 1158844-72-4 C₄₃H₄₂B₂O₄ 
• 1158844-73-5 C₇₁H₄₄ 
• 1158844-75-7 C₄₉H₄₆B₂O₄ 
• 1158844-46-2 C₇₇H₄₈ 
• 1259313-86-4 spiro(2,7-bis[4-methoxyphenyl]fluorene-9,9'-fluorene) 
• 1259293-45-2 C₃₉H₂₀F₈ 
• 1245645-82-2 2-bromo-7-(4-(diphenylamino)phenyl)-9,9-spirobifluorene 
• 1336947-37-5 N,N,N',N'-tetra-p-tolyl-9,9'-spirobifluorene-2,7-diamine 
• 1245652-70-3 3-(5-(2-(4-(diphenylamino)phenyl)-9,9-spirobifluoren-7-yl)-3-hexylthiophene-2-yl)-2-cyanoacrylic acid 

Relevant articles and documents

A highly fluorescent water soluble spirobifluorene dye with a large Stokes shift: Synthesis, characterization and bio-applications

The first water-soluble spirobifluorene derivative has been synthesized, which exhibits high fluorescence quantum yield and a large Stokes shift (>100 nm). Proteins induce changes in the emission color, allowing to reach the nanomolar detection limit. Cellular uptake and cytotoxicity studies in living cells revealed its biocompatibility, indicating potential application for live cell imaging.

Method for synthesizing 9,9'-spirobifluorene derivative

The invention relates to a method for synthesizing a 9,9'-spirobifluorene derivative, and belongs to the field of organic chemical synthesis. The method comprises the following steps: activating a C-Fbond in tetrahydrofuran under inert gas protection through reduction and lithiation reaction of raw materials of 2-fluorobiphenyl and a metal lithium sheet, thus establishing 2-biphenyl lithium; thenenabling the 2-biphenyl lithium to react with a fluorenone derivative, hydrolyzing, drying a solvent by distillation, and carrying out ring closing on solid in acetic acid, thus synthesizing the 9,9'-spirobifluorene derivative. According to the method disclosed by the invention, the 2-fluorobiphenyl in low cost is adopted as a raw material to replace 2-bromobiphenyl commonly adopted by a traditional method, the production cost is low, and reaction conditions are gentle; an applicable substrate range of the method is wide, and a new thought is provided for synthesis of the 9,9'-spirobifluorenederivative.

Electron Transfer around a Molecular Corner

The distance dependence of electron transfer (ET) is commonly investigated in linear rigid rod-like compounds, but studies of molecular wires with integrated corners imposing 90° angles are very rare. By using spirobifluorene as a key bridging element and by substituting it at different positions, two isomeric series of donor-bridge-acceptor compounds with either nearly linear or angled geometries were obtained. Photoinduced ET in both series is dominated by rapid through-bond hole hopping across oligofluorene bridges over distances of up to 70 ?. Despite considerable conformational flexibility, direct through-space and through-solvent ET is negligible even in the angled series. The independence of the ET rate constant on the total number of fluorene units in the angled series is attributed to a rate-limiting tunneling step through the spirobifluorene corner. This finding is relevant for multidimensional ET systems and grids in which individual molecular wires are interlinked at 90° angles.