500901-89-3

Basic information

• Product Name: 2,7-Dibromofluorene
• Synonyms: 2,7-dibromo-9H-fluorene; K0005
• CAS NO: 500901-89-3
• Molecular Formula: C₁₃H₈Br₂
• Molecular Weight: 324.0106
• Mol File: 500901-89-3.mol

Chemical Properties

• Melting Point: 164-167℃
• Boiling Point: 402.7°C at 760 mmHg
• Flash Point: 230.9°C
• Density: 1.793g/cm³
• Vapor Pressure: 2.5E-06mmHg at 25°C
• Refractive Index: 1.691
• CAS DataBase Reference: 2,7-Dibromofluorene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,7-Dibromofluorene(500901-89-3)
• EPA Substance Registry System: 2,7-Dibromofluorene(500901-89-3)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S37/39:
• Hazardous Substances Data: 500901-89-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,7-Dibromofluorene is used as a building block for organic synthesis, particularly in the production of pharmaceuticals and materials. Its reactivity, conferred by the bromine atoms, allows for the creation of a variety of complex organic compounds, making it an essential component in the synthesis process.
Used in Organic Electronics:
2,7-Dibromofluorene is utilized in the development of organic electronics due to its semiconducting properties. Its capacity to form stable thin films makes it a promising candidate for applications in electronic devices and components.
Used in Pharmaceutical Production:
As a key intermediate in the synthesis of pharmaceuticals, 2,7-Dibromofluorene plays a crucial role in the development of new drugs. Its unique structure and reactivity contribute to the creation of novel therapeutic agents.
Used in Material Science:
In the field of material science, 2,7-Dibromofluorene is employed for the development of new materials with specific properties. Its chemical structure and reactivity are harnessed to engineer materials with tailored characteristics for various applications.

Upstream product

• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 216312-73-1 3,6-dibromofluoren-9-one 
• 10034-85-2 hydrogen iodide 
• 53348-05-3 3,6-dibromo-phenanthrene-9,10-dione 
• 84-11-7 9,10-phenanthrenequinone 

Downstream Products

• 865702-19-8 3, 6?dibromo?9, 9?dimethyl?9H?fluorene 

Relevant articles and documents

Polymer library comprising fluorene and carbazole homo- and copolymers for selective single-walled carbon nanotubes extraction

To date, (n, m) single-walled carbon nanotubes (SWNTs) cannot be selectively synthesized. Therefore, postprocessing of SWNTs including solubilization and sorting is necessary for further applications. Toward this goal, we have synthesized a polymer library consisting of fluorene- and carbazole-based homo- and copolymers. Variations of the connection of these aromatics together with the incorporation of further conjugated monomers give access to a broad diversity of polymers. Their ability to selectively wrap specific (n, m) species is investigated toward HiPco SWNTs raw material which contains more than 40 (n, m) species. Absorption and fluorescence spectroscopies were used to analyze SWNTs/polymer suspensions. These results provide evidence for selective SWNTs/polymer interactions and allow a more detailed assessment of polymer structure-property relationships, thus paving the way toward custom synthesis of polymers for single (n, m) SWNTs extraction.

Engineering heteroatoms with atomic precision in donor-acceptor covalent triazine frameworks to boost photocatalytic hydrogen production

Porous organic polymers (POPs) with conjugated structures, high surface areas and variable building blocks are shown to possess enormous potential to be used in photocatalytic hydrogen evolution reaction. However, photocatalytic performances of most POPs are impeded by insufficient charge transfer and rapid charge recombination. Herein, based on covalent triazine frameworks (CTFs), we show a strategy to boost the photocatalytic performance by enhancing charge transfer/separation, where the donors can be easily tailored through substituting different heteroatoms with atomic precision in a series of donor-acceptor CTFs, resulting in optimal energy levels and enhanced charge transfer ability. Among them, the N-doped fluorene (carbazole) bearing the strongest electron donating ability achieves the highest photocatalytic performance among POPs, with an exceptionally high hydrogen evolution rate of 538 μmol h-1 under visible light irradiation. Photophysical and electrochemical studies reveal that the high photocatalytic performance is attributed to high charge transfer efficiency and low charge recombination in these heteroatom-doped donor-acceptor CTFs. The work demonstrates that adjusting the push-pull interaction between the donor and acceptor via heteroatom engineering is an effective strategy to increase photocatalytic performance.

Synthesis and characterization of a new series of dibenzofulvene based organic dyes for DSSCs

Three new 2D-π-A dyes (TK4, TK5 and TK6), composed of diarylamine donor groups, a dibenzofulvene-thiophene core as the π-bridge, and a cyanoacrylic acid anchoring group as the acceptor, have been successfully designed, synthesized, and characterized both experimentally and computationally. The performance in DSSC solar cells has been also studied. Octyloxy chains were introduced on the backbone of the dye, in order to increase donor capability, avoid aggregation side effects and increase physical insulation between electrolyte system and the TiO2 layer. The dye containing the octyloxy chains on the donor group and two thiophene ring as an extension of π-bridge showed the best photovoltaic performance with a maximum of solar energy-to-electricity conversion yield of 7.8% under AM 1.5 irradiation (100 mW/cm2).

Synthesis and photovoltaic performance of dibenzofulvene-based organic sensitizers for DSSC

Three novel 2D-π-A metal-free organic dyes TK 7–9 containing a dibenzofulvene (DBF) linked to two thiophene units as the π-bridge, diarylamines with and without alkoxy chains as donor groups and the cyanoacrylic acid moiety as the acceptor and anchoring group were synthesized. The new dyes TK were characterized by optical and electrochemical measurements and density functional theory calculations and were used as sensitizers in liquid dye-sensitized solar cells. The effects of alkoxy-functionalization of donor moiety and of hexyl chain insertion onto one thienyl ring of π-linker on dye properties and performances were investigated. The results discover the dye TK7, bearing two simple diphenylamine groups without alkoxy chains, exhibits the best behavior in terms of light absorption and cell performance (PCE of 7.9% and photovoltaic parameters of Jscof 17.82?mA?cm?2, Vocof 670?mV and FF of 0.66). Lower power conversion efficiencies of 6.3% and 6.1% were found for TK8 and TK9, respectively, as a consequence of the presence of the alkoxy chains.

Molecular engineering and synthesis of symmetric metal-free organic sensitizers with A-π-D-π-A architecture for DSSC applications: the effect of bridge unit

Herein, we report the design and synthesis of six symmetric metal-free organic sensitizers (llyu1a, llyu1b, llyu1c, llyu2a, llyu2b, and llyu2c) based on fluorene or dimethyl fluorene donors core carrying double acceptors. All these dyes were characterized

A Family of Superhelicenes: Easily Tunable, Chiral Nanographenes by Merging Helicity with Planar π Systems

We designed a straightforward synthetic route towards a full-fledged family of π-extended helicenes: superhelicenes. They have two hexa-peri-hexabenzocoronenes (HBCs) in common that are connected via a central five-membered ring. By means of structurally altering this 5-membered ring, we realized a versatile library of molecular building blocks. Not only the superhelicene structure, but also their features are tuned with ease. In-depth physico-chemical characterizations served as a proof of concept thereof. The superhelicene enantiomers were separated, their circular dichroism was measured in preliminary studies and concluded with an enantiomeric assignment. Our work was rounded-off by crystal structure analyses. Mixed stacks of M- and P-isomers led to twisted molecular wires. Using such stacks, charge-carrier mobilities were calculated, giving reason to expect outstanding hole transporting properties.

PHENANTHROLINE-BSAED COMPOUND AND USE THEREOF

The present invention discloses a novel phenanthroline-based compound is represented by the following formula (I), the organic EL device employing the phenanthroline-based compound as hole blocking material/electron transport material or phosphorescent ho

Synthesis and supramolecular assembly of pentacyclic dithienofluorene and diselenophenofluorene derivatives

2,7-Diiodo-3,6-dibromofluorene and 2,7-dichloro-3,6-dibromofluorene have been successfully synthesized. The two key intermediates enable us to implement a regioselective Sonogashira reaction followed by intramolecular thiolate/acetylene cyclization, forming two regiospecific pentacyclic dithieno[2,3-b:7,6-b′]fluorene (2,7-DTF) and dithieno[3,2-b:6,7-b′] fluorene (3,6-DTF) isomeric molecules, respectively. By using a similar strategy, selenophene-based diselenopheno[2,3-b:7,6-b′]fluorene (2,7-DSF) as well as diselenopheno[3,2-b:6,7-b′]fluorene (3,6-DSF) were also prepared. The isomeric and sulfur/selenium effects determine the optical, electrochemical, and orbital properties. X-ray crystallography revealed that 2,7-DTF and 3,6-DTF molecules assemble into supramolecular helical structures.

Vacuum-processable ladder-type oligophenylenes for organic-inorganic hybrid structures: Synthesis, optical and electrochemical properties upon increasing planarization as well as thin film growth

A novel synthetic route to even-numbered ladder-type oligo(p-phenylene)s (LOPPs) carrying no solubilizing groups to facilitate vacuum-processing is presented. The influence of increasing bridging adjacent phenylene units on the optical and electrochemical properties is discussed in the series of p-sexiphenyl 6P, terfluorene 3F, and ladder-type sexiphenyl L6P. The influence of the extension of the π-system is taken into consideration as well. Furthermore it is shown that highly ordered thin films of L6P on alumina surfaces can be prepared by organic molecular beam deposition (OMBD).

Synthesis and properties of cyclic ethylene-bridged 3,6-fluorene dimer and its linear analogues

Three oligomers of ethylene-bridged 3,6-fluorene were synthesized starting from phenanthrenequinone. McMurry reaction was applied to synthesize the cyclic compound. Horner-Emmons reaction was used to synthesize the linear compounds with all-trans configuration. The crystal structure of the cyclic compound was described. The optical and electronic properties of these compounds were fully characterized and compared.