226070-05-9

Usage

Uses

Used in Electronic Devices:
2-Bromo-9,9-dihexyl fluorene is used as a key component in the development of electronic devices due to its thermal stability and solubility, which contribute to the performance and reliability of these devices.
Used in Polymers:
In the polymer industry, 2-Bromo-9,9-dihexyl fluorene is utilized as a building block for synthesizing polymers with specific properties, such as improved thermal stability and solubility, enhancing their applicability in various applications.
Used in Organic Photovoltaics:
2-Bromo-9,9-dihexyl fluorene is employed as a crucial material in the fabrication of organic photovoltaics, where its properties contribute to the efficiency and stability of solar cells.
Used in Chemical Research and Development:
In the realm of chemical research and development, 2-Bromo-9,9-dihexyl fluorene is used as a versatile chemical for creating innovative materials with tailored properties, driving advancements in materials science and technology.

Upstream product

• 123863-97-8 9,9-dihexyl-9H-fluorene 
• 86-73-7 9H-fluorene 
• 111-25-1 1-bromo-hexane 
• 1133-80-8 2-bromo-9H-fluorene 

Downstream Products

• 852042-91-2 9,9-dihexyl-2-(2'-phenyl-1-ethynyl)fluorene 
• 1285536-59-5 N,N-di(7-bromo-9,9-dihexyl-2-fluorenyl)-N-phenylamine 
• 1285536-60-8 4-[bis(2-bromo-9,9-dihexyl-7-fluorenyl)amino]benzaldehyde 
• 1285536-61-9 7-bromo-N-(2-bromo-9,9-dihexyl-7-fluorenyl)-9,9-dihexyl-N-[4-[2-(thio-phen-2-yl)vinyl]phenyl]fluoren-2-amine 
• 1285536-62-0 5-[4-[bis(2-bromo-9,9-dihexyl-7-fluorenyl)amino]styryl]thiophene-2-carbaldehyde 
• 1394039-76-9 C₇₀H₆₁N₅ 
• 371193-08-7 9,9-dihexylfluorene-2-boronic acid 

Relevant academic research and scientific papers

Synthesis, optical, electrochemical, and thermal properties of conjugated α-fluorenyl oligothiophenes

A series of new α-fluorenyl oligothiophenes up to the pentamer have been synthesized using Suzuki cross-coupling and bromination reactions. The optical, electrochemical, and thermal properties of these materials can be tuned by varying the number of thiophene rings. The longer oligomers (n ≥ 4) were stable, crystalline, and unreactive to electrochemical oxidative dimerization.

Oligofluorenes as polymeric model compounds for providing insight into the triplets of ketone and ketylimine derivatives

A series of oligofluorenes ranging between one and three repeating units were prepared as structurally well-defined representative models of polyfluorenes. The photophysics of the oligofluorene models were investigated both by laser flash photolysis and steady-state fluorescence. The effects of the ketone and ketylimine functional groups in the 9-position on the photophysical properties, notably the triplet quantum yield (ΦTT) by intersystem crossing and the absolute fluorescence quantum yields (Φfl), were investigated. The singlet depletion method was used to determine both the ΦTT and molar absorption coefficients of the observed triplets (εTT). Meanwhile, the absolute Φfl were determined using an integrating sphere. It was found that both the ketone and ketylimine substituents and the degree of oligomerization contributed to quenching the oligofluorene fluorescence. For example, the Φfl was quenched 5-fold with the ketylimine and ketone substituents for the bifluorenyl derivatives compared to their corresponding 9,9-dihexyl bifluorenyl counterparts. Meanwhile, the Φfl quenching increased 14 times with the trifluorenyl ketone and ketylimine derivatives. Measured ΦTT values ranged between 22 and 43% for the difluorenyl derivatives with εTT on the order of 13 000 cm-1 M-1. The ΦTT decreased to TT when the degree of oligomerization was increased to 3. A new fluorescence emission at 545 nm formed at low temperatures for the ketone and ketylimine oligofluorene derivatives. The emission intensity was dependent on the temperature, and it disappeared at room temperature.

Design of differently P-substituted 4i PO fluorescent tetraphosphonate cavitands

Experimental approaches to tetraphosphonate cavitands bearing fluorenyl-phosphonate bridges are reported. Different routes are described depending on the substitution on the cavitand structure. Tetra-, tri- and di-bridged phosphonate cavitands have been p

Amorphous iridium complexes for electrophosphorescent light emitting devices

Iridium complexes with fluorene-modified phenylpyridine ligands are resistant to crystallization and can be used in the fabrication of single layer light emitting diodes.

Photophysical, electrochemical, and crystallographic investigation of conjugated fluoreno azomethines and their precursors

The photophysical investigation of amino- and aldehyde-substituted fluorenes revealed that these compounds are not only highly fluorescent, but dissipation of their singlet excited energy occurs by a combination of nonradiative means involving intersystem crossing (ISC) and internal conversion (IC). Quantification of the triplet state formed by ISC was possible by laser-flash photolysis (LFP). The efficiency by which this manifold was populated varied between 10 and 40% depending on the fluorene substitution. Condensation of these aldehyde and amine precursors yielded conjugated thiopheno azomethines with robust covalent bonds. Fluorescence of the azomethine fluorene derivatives was reduced relative to their precursors while the degree of IC remained unchanged. Deactivation of the singlet excited state occurred predominately by ISC and the resulting triplet state was rapidly and efficiently quenched by energy transfer by the azomethine linkage. Cyclic voltammetry of the fluoreno azomethines showed both oxidation and reduction processes, and the measured redox potentials and the band-gaps are lower than a bisfluorene analogue. The fluoreno azomethine LUMO energy levels are sufficiently low, making them compatible with common cathodes, therefore eliminating the use of an electron-injection layer. The Royal Society of Chemistry 2007.

Synthesis, optical and electrochemical properties of 2-[(9H-fluoren-2-yl)aryl]-1H-benz[d]imidazole and 2,7-bis[(1H-benz[d]imidazol-2-yl)aryl]-9H-fluorene derivatives

A series of 2-[(9H-fluoren-2-yl)aryl]-1H-benzo[d]imidazoles 11-13 and 2,7-bis[(1H-benzo[d]imidazol-2-yl)aryl]-9H-fluorenes 14-16 containing different linking aromatic units were synthesized in good yields. Their absorption and fluorescence properties were

Difluorenyl carbo-Benzenes: Synthesis, Electronic Structure, and Two-Photon Absorption Properties of Hydrocarbon Quadrupolar Chromophores

The synthesis, crystal and electronic structures, and one- and two-photon absorption properties of two quadrupolar fluorenyl-substituted tetraphenyl carbo-benzenes are described. These all-hydrocarbon chromophores, differing in the nature of the linkers b

Synthesis and characterization of N-carbazole end-capped oligofluorenes

A series of N-carbazole end-capped oligofluorenes (CFn, n = 1-3) were synthesized. The 9-position of the carbazole moiety was attached to the terminal ends of the oligofluorene cores using an Ullmann coupling reaction. These molecules exhibit red shifts in absorption and photoluminescence spectra with respect to the number of fluorene units and excellent electrochemical reversibility. They were found to be potential blue light-emitting or hole-transporting materials for organic light-emitting diodes (OLEDs).

Two-photon absorption properties of four new pentacoordinated diorganotin complexes derived from Schiff bases with fluorene

In this paper we report the synthesis and characterization of four novel pentacoordinated diorganotin complexes, obtained through a methodology that involves a multicomponent reaction of 4-([9H-fluorene-2-yl]ethynyl)-2-hydroxybenzaldehyde, 2-amino-5-nitrophenol and diphenyl or dibutyl-tin oxides. Diorganotin complexes 8–11 were obtained in high yields (70–80%) and were fully characterized by solution NMR (1H, 13C and 119Sn), high resolution mass spectrometry (ESI-TOF) and ATR-FTIR. The optical properties were investigated by UV/Vis spectroscopy and Two-Photon Excitation Fluorescence (TPEF). The One-Photon Absorption (OPA) spectra shows two bands located around 400 and 500 nm, additionally, in the Two-Photon Absorption (TPA) spectra there is one main band located around 750 nm characterized by maximum values of TPA cross section (σTPA) in the range 450–500 GM with a secondary band located at 1000 nm with maximum σTPA values of 70 GM; the maximum brightness was observed for 2,2-Dibutyl-6-aza-1,3-dioxa-11-([9,9-dihexyl-9H-fluorene-2-yl]ethynyl)-16-nitro-2-stanna-[d,h]dibenzocyclononene with a value of 150 GM. A theoretical approach within the framework of DFT was applied to study the electronic transitions, showing that the 500 nm band is mainly associated to a HOMO→LUMO transition, and the band at 400 nm to a HOMO-1→LUMO transition. As main highlights the quantum efficiency of fluorescence of these excited states is as large as 0.43 due to the presence of the tin atom which favors molecular rigidity, these compounds possess TPA responses which are significantly enhanced with respect to related organotin chromophores previously reported.

Simple fluorene oxadiazole-based Ir(iii) complexes with AIPE properties: Synthesis, explosive detection and electroluminescence studies

Two novel phosphorescent Ir(iii) complexes, Ir(fom)2(pic) and Ir(fof)2(pic), containing fluorene oxadiazole groups have been synthesized and characterized. The photophysical properties of the complexes have been investigated. Interestingly, both complexes exhibited aggregation-induced phosphorescent emission. The X-ray diffraction study showed that the AIPE properties resulted from weak π-π and C-H?N hydrogen-bonding interactions in the aggregated state restricting the rotation of the phenyl groups in the cyclometalating ligands. Owing to the sensitive and selective luminescence quenching of the complexes using picric acid (PA), the complexes were used for PA detection in aqueous media. Additionally, electroluminescence devices have been fabricated using the complexes at 5%-30% doping concentrations. The devices based on Ir(fof)2(pic) obtained the highest luminance 11877 cd m-2 and current efficiency 23.2 cd A-1, which implied that the incorporation of fluorine could improve the electron affinity and ameliorate the capability of electron injection or transporting.