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

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

Uses

Used in Organic Light Emitting Diodes (OLEDs):
2,7-Dibromo-9,9'-spirobifluorene is used as a precursor for the preparation of 9,9'-spirobifluorene-based small molecules. These small molecules are then utilized as host materials in the manufacturing of organic light emitting diodes (OLEDs). The high photoluminescence and electroluminescent quantum efficiency of 2,7-Dibromo-9,9'-spirobifluorene contribute to the improved performance and efficiency of OLEDs, making them suitable for various display and lighting applications.
Used in Organic Electronics Industry:
In the organic electronics industry, 2,7-Dibromo-9,9'-spirobifluorene is used as a key component in the synthesis of advanced materials with enhanced optical and electronic properties. Its high quantum efficiency and photoluminescent characteristics make it an ideal candidate for the development of novel organic electronic devices, such as solar cells, sensors, and transistors, where improved performance and efficiency are crucial.

Upstream product

• 2052-07-5 2-Bromobiphenyl 
• 6344-61-2 9H-fluoren-1-ol 
• 14348-75-5 2,7-dibromofluorene-9-one 
• 100-58-3 phenylmagnesium bromide 
• 583-53-9 2,3-dibromobenzene 
• 159-66-0 9,9'-spirobifluorene 
• 98-80-6 phenylboronic acid 
• 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

• 128055-74-3 2,2',7,7'-tetrabromo-9,9'-spirobifluorene 
• 1185882-63-6 4-(2-bromo-9,9-spirobifluoren-7-yl)benzaldehyde 
• 1185882-64-7 4-(2-(bis(9,9-dimethyl-9H-fluoren-7-yl)amino)-9,9-spirobifluoren-7-yl)benzaldehyde 
• 1185882-68-1 3-(4-(2-(bis(9,9-dimethyl-9H-fluoren-7-yl)amino)-9,9-spirobifluoren-7-yl)phenyl)-2-cyanoacrylic acid 
• 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 
• 1245644-24-9 5-(2-(4-(diphenylamino)phenyl)-9,9-spirobifluoren-7-yl)-3-hexylthiophene-2-carbaldehyde 

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.

Versatile Porous Poly(arylene ether)s via Pd-Catalyzed C-O Polycondensation

Porous organic polymers (POPs) with strong covalent linkages between various rigid aromatic structural units having different geometries and topologies are reported. With inherent porosity, predictable structure, and tunable functionality, POPs have found utility in gas separation, heterogeneous catalysis, sensing, and water treatment. Poly(arylene ether)s (PAEs) are a family of high-performance thermoplastic materials with high glass-transition temperatures, exceptional thermal stability, robust mechanical properties, and excellent chemical resistance. These properties are desirable for development of durable POPs. However, the synthetic methodology for the preparation of these polymers has been mainly limited in scope to monomers capable of undergoing nucleophilic aromatic substitution (SNAr) reactions. Herein, we describe a new general method using Pd-catalyzed C-O polycondensation reactions for the synthesis of PAEs. A wide range of new compositions and PAE architectures are now readily available using monomers with unactivated aryl chlorides and bromides. Specifically, monomers with conformational rigidity and intrinsic internal free volume are now used to create porous organic polymers with high molecular weight, good thermal stability, and porosity. The reported porous PAEs are solution processable and can be used in environmentally relevant applications including heavy-metal-ion sensing and capture.

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.

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.

9, 9' - Spirobifluorene preparation of

PROBLEM TO BE SOLVED: To provide a method for industrially advantageously manufacturing 9,9'-spirobifluorenes.SOLUTION: By performing a reaction in the presence of a non-aqueous solvent when an intermediate (9-(2-biphenyl)-9-fluorene alcohols) is ring-closed, 9,9'-spirobifluorenes are obtained even when a large amount of acid is not used as a solvent. In the manufacture of the intermediate, the 9,9'-spirobifluorenes can be more easily manufactured by extracting the intermediate 9-(2-biphenyl)-9-fluorene alcohols obtained by a Grignard reaction between 2-halo biphenyl and 9-fluorenones from a reaction mixture by a water-insoluble solvent instead of a method of isolating the intermediate by a crystallization filtration being a conventional method.

Spirofluorene compound and light-emitting device thereof

The invention relates to the technical field of organic light-emitting materials and particularly relates to a spirofluorene compound and a light-emitting device thereof. A spirobifluorene compound is selected from a compound represented by formula I (shown in the description), wherein Y1 and Y2 respectively independently represent hydrogen, electron-withdrawing groups or electron-donating groups; at least one of X1 and X2 represents a substituent represented by formula II (shown in the description); M represents -S-, -P-, -SO-, -SO2-, -S(=S)-, -S(=S)(=S)-, -PO-, -PO2-, -P(=S)-, -P(=S)(=S)- and -C(=O)-; N1, N2, N3 and N4 respectively independently represent carbon atoms or nitrogen atoms; and n represents an integer of 0-4. The spirobifluorene compound disclosed by the invention has an A-D-A chemical structure, and a spatial dihedral angle close to 90 degrees is formed between an electron-donating D unit and an electron-withdrawing A unit, so that HOMO-LUMO track separation of a fluorescent material is beneficially thermally activated and delayed, so as to obtain ideal deltaEST.

Synthesis and Exciton Dynamics of Donor-Orthogonal Acceptor Conjugated Polymers: Reducing the Singlet-Triplet Energy Gap

The presence of energetically low-lying triplet states is a hallmark of organic semiconductors. Even though they present a wealth of interesting photophysical properties, these optically dark states significantly limit optoelectronic device performance. Recent advances in emissive charge-transfer molecules have pioneered routes to reduce the energy gap between triplets and "bright" singlets, allowing thermal population exchange between them and eliminating a significant loss channel in devices. In conjugated polymers, this gap has proved resistant to modification. Here, we introduce a general approach to reduce the singlet-triplet energy gap in fully conjugated polymers, using a donor-orthogonal acceptor motif to spatially separate electron and hole wave functions. This new generation of conjugated polymers allows for a greatly reduced exchange energy, enhancing triplet formation and enabling thermally activated delayed fluorescence. We find that the mechanisms of both processes are driven by excited-state mixing between π-πand charge-transfer states, affording new insight into reverse intersystem crossing.

Engineering the Interconnecting Position of Star-Shaped Donor–π–Acceptor Molecules Based on Triazine, Spirofluorene, and Triphenylamine Moieties for Color Tuning from Deep Blue to Green

Pi-conjugated organic molecules featuring the donor–bridge–acceptor (D–π–A) structure have been widely used in semiconducting materials owing to their rigid structure, good thermal stability, excellent charge transfer, and high emission efficiency. To investigate the effect of the D–π–A molecular structure on the photophysical properties, in this contribution, three star-shaped D–π–A isomers based on the 2,4,6-triphenyl-1,3,5-triazine, spirofluorene, and triphenylamine moieties, that is, p-TFTPA, mp-TFTPA, and m-TFTPA, were synthesized by elaborately engineering the interconnecting position in the building-block units. The optophysical properties of these compounds were systematically explored by experiments and theory calculations. Definitively, changing the interconnecting position in these molecules played a significant role in the degree of π conjugation, which resulted in tunable emission colors from deep blue to green. Moreover, these isomers were employed as emissive dopants in organic light-emitting diodes. The highest external quantum efficiency of 2.3 % and current efficiency of 6.2 cd A?1 were achieved by using the p-TFTPA based device. This research demonstrates a feasible way to realize blue emitters by engineering D–π–A conjugation.

A kind of 9, 9 the- [...] method for synthesis of derivatives of fluorene

The invention discloses a synthesis method of a 9,9'-spirobifluorene derivative, and belongs to the field of organic chemical synthesis. The method comprises the steps that 2-bromochlorobenzene as a raw material acts with phenylmagnesium bromide and then reacts with bromofluorenone at 50-100 DEG C in a methyltetrahydrofuran solvent, hydrolysis and filtration are performed, solid performs closed-loop synthesis under acid catalysis to produce bromo-9,9'-spirobifluorene, and bromo-9,9'-spirobifluorene reacts with lithium diphenylphosphide to synthesize the 9,9'-spirobifluorene diphenylphosphine derivative. The synthesis method is simple in process; raw materials are low in price and easy to obtain; the production cost of series products is obviously lowered during synthesis; and the application of the fluorene derivative in design and synthesis of organic photoelectric materials as an intermediate is extended.

MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES

The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.