570414-33-4

Usage

Uses

Used in Organic Solar Cells:
2,7-DIBROMO-9,9-BIS(6-BROMOHEXYL)FLUORENE,99% is used as a reactant in the preparation of electron transport materials for organic solar cells. Its unique chemical structure allows for efficient charge transport and improved device performance.
Used in Cationic Tetraarylethene Oligoelectrolytes:
In the field of organic synthesis, 2,7-DIBROMO-9,9-BIS(6-BROMOHEXYL)FLUORENE,99% is utilized in the cross-coupling synthesis of cationic tetraarylethene oligoelectrolytes. These oligoelectrolytes have potential applications in the development of novel materials for electronic devices and sensors.
Used in π-Conjugated Polymers with Pendant Coumarins:
2,7-DIBROMO-9,9-BIS(6-BROMOHEXYL)FLUORENE,99% is also employed in the preparation of π-conjugated polymers with pendant coumarins. These polymers exhibit interesting photophysical properties and have potential applications in optoelectronic devices, such as organic light-emitting diodes (OLEDs) and photovoltaic cells.

Upstream product

• 629-03-8 1 ,6-dibromohexane 
• 16433-88-8 2,7-dibromo-9H-fluorene 
• 86-73-7 9H-fluorene 

Downstream Products

• 851775-62-7 2,2′-(9,9-bis(6-bromohexyl)-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxoborolane) 
• 1226773-97-2 C₃₉H₄₈Br₃NO₅ 
• 1226773-98-3 C₄₇H₆₇Br₂N₅O₅ 
• 1226773-99-4 C₆₅H₉₇Br₂N₅O₁₁ 
• 1226773-95-0 C₃₁H₃₇Br₂NO₂ 
• 1226773-96-1 C₃₉H₄₉Br₂NO₆ 
• 1256244-39-9 2,7-di(4'-phenylmethanol)-9,9-bis(6'-bromohexanyl)fluorene 
• 1351954-77-2 4,4'-(9,9-bis(6-bromohexyl)-9H-fluorene-2,7-diyl)diphenol 
• 1621070-12-9 C₆₅H₆₀N₂O₄ 
• 1414787-64-6 C₁₁₃H₈₈Br₂N₈O₂ 
• 1282537-61-4 2,7-dibromo-9,9-bis(6-phenoxyhexyl)-9H-fluorene 

Relevant academic research and scientific papers

Two-photon fluorescence imaging of sialylated glycans: In vivo based on a sialic acid imprinted conjugated polymer nanoprobe

We have designed and synthesized a sialic acid (SA)-imprinted conjugated polymer nanoprobe with two-photon fluorescence properties, which exhibits specific recognition ability to the target SA and has been used for monitoring sialylated glycan levels selectively in vivo.

Optical and electronic properties of fluorene-based copolymers and their sensory applications

A series of novel, fluorene-based conjugated copolymers, poly[(9,9-bis{propenyl}-9H-fluorene)-co-(9,9-dihexyl-9H-fluorene)] (P1), poly[(9,9-bis{carboxymethylsulfonyl-propyl}fluorenyl-2,7-diyl)-co-(9, 9-dihexyl-9H-fluorene)] (P2) and poly[(9,9-dihexylfluorene)-co-alt-(9,9-bis-(6- azidohexyl)fluorene)] (P3), are synthesized by Suzuki coupling reactions and their electrochemical properties, in the form of films, are investigated using cyclic voltammetry. The results reveal that the polymer films exhibit electrochromic properties with a pseudo-reversible redox behavior; transparent in the neutral state and dark violet in the oxidized state. Among the three polymers, P2 possesses the shortest response time and the highest coloration efficiency value. These polymers emit blue light with a band gap value of around 2.9 eV and have high fluorescent quantum yields. Their metal ion sensory abilities are also investigated by titrating them with a number of different transition metal ions; all of these polymers exhibit a higher selectivity toward Fe3+ ions than the other ions tested with Stern-Volmer constants of 4.41 × 106M-1, 3.28 × 107M -1, 1.25 × 106M-1, and 6.56 × 106M-1 for P1, P2, water soluble version of P2 (P2S) and P3, respectively.

Conjugated polyfluorene-based reversible fluorescent sensor for Cu(II) and cyanide ions in aqueous medium

A blue emissive polyfluorene bearing sulfate functionality in the side chain (PFS), as a sensory polymer to selectively report the presence of Cu 2+ (detection limit down to 2.5 μM) based on the fluorescence turn-off. Surprisingly, the quenched luminescence of PFS by Cu 2+ could be turned on after the addition of CN- (detection limit down to 6 μM), making PFS a sensitive, selective, and reversible cyanide probe.

Creating a pseudometallic state of K+ by intercalation into 18-crown-6 grafted on polyfluorene as electron injection layer for high performance PLEDs with oxygen- and moisture-stable Al cathode

Polymer light-emitting diodes (PLEDs) suffer from inadequate lifetimes because of the use of environmentally sensitive metals as the cathodes. We present the use of water/methanol-soluble polyfluorene grafted with 18-crown-6 chelating to K+ as the electron-injection layer (EIL) for deep-blue-emission PLEDs, allowing the use of environmentally stable Al as the cathode since electron donation from the 18-crown-6 can reduce K+ to a stable "pseudometallic state", enabling it to act as an intermediate step for electron injection. Furthermore, when poly(ethylene oxide) was blended into the EIL to provide hole blocking (HB), the device exhibited the highest performance reported to date for a deep-blue-emission PLED based on a conjugated polymer as the emitting layer, with a brightness of 54-800 cd/m2 and an external quantum efficiency of 5.42%. The use of such an EI-HB layer opens a broad avenue leading toward industrialization of PLEDs.

Polyfluorenes with phosphonate groups in the side chains as chemosensors and electroluminescent materials

Polyfluorenes (P1 and P2) with phosphonate groups in the side chains were designed and synthesized. Their absorption and photoluminescence spectra in solutions are solvent dependent and exhibit a red shift up to 14 and 6 nm, respectively, with increasing solvent polarity. The polymers are highly soluble in ethanol with a solution photoluminescence quantum yield of 0.74. Polymer P2 in thin film cast from ethanol shows high intrachain order as revealed by red-shifted absorption spectrum and emission spectrum along with well-resolved vibronic structure. Both P1 and P2 are highly sensitive and selective Fe 3+ sensory materials, and the sensitivity is much higher than that of model compounds 3 and 4. The highest sensitivity was observed with polymer P1, and a 210-fold fluorescence quenching in dichloromethane was achieved. Polymer light-emitting diodes (PLEDs) were also fabricated to investigate the electroluminescent properties. A luminous efficiency of 1.49 cd/A with Commission Internationale de L'Eclairage (CIE) coordinates of (0.171, 0.131) at 100 cd/m2 and a maximum brightness of 1750 cd/m2 have been demonstrated.

A conjugated polyelectrolyte interfacial modifier for high performance near-infrared quantum-dot photodetectors

The photodetection properties of near-infrared quantum-dot photodetectors (NIR-QPDs) have been significantly improved by introducing novel cationic conjugated polyelectrolytes (CCPs) on ZnO. The formation of a quaternary ammonium salt at the end of the pendant groups of the CCPs generates a permanent dipole moment on the ZnO surface and effectively modifies the work function of ZnO, improving the charge transport at the interfaces between the ZnO and QD layers. The cationic charge density and the geometrical structures of CCP1-3 had crucial effects in determining the photo-responsivity (R) and detectivity (D?) of the NIR-QPDs. The higher cationic charge density of CCP2 improved the electron accepting properties of ZnO, resulting in 1.6-5.1-fold increased R values under 940 nm IR irradiation (0.1 mW cm-2,-1 V) compared to the ZnO-, ZnO/CCP1-, and ZnO/CCP3-based devices. Notably, the horizontally-aligned backbone of CCP2 toward the substrate gives a uniform film surface and insulating layer on ZnO, which improved the charge transport and maintained a relatively low and constant dark current under negative bias. As a result, D? of the CCP2-treated NIR-QPDs was increased by up to 1880% compared to the pristine ZnO-based devices, and by 200-250% compared to the CCP1- A nd CCP3-based devices.

Synthesis and photophysical characterization of an ionic fluorene derivative for blue light-emitting electrochemical cells

Abstract A highly fluorescent an ionic fluorene derivative 1 was synthesized and its photophysical, electrochemical and electroluminescence characteristics were investigated. Deep blue emissions were observed for compound 1 in solid as well as in dilute solutions. The synthesized compound shows high fluorescence quantum yield around 77% indicates that compound 1 can perform its role as efficient ionic emitter in LEC devices. Light-emitting electrochemical cell (LEC) devices were fabricated incorporating compound 1 without (device I) and with (device II) ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate (BMIM·PF6). Devices I and II exhibited blue electroluminescence maximum centered at 455 and 454 nm with CIE coordinates of (0.15, 0.21) and (0.16, 0.22), respectively. Maximum luminance and current efficiency of 1105 cd m-2 and 0.14 cd A-1 respectively, has achieved for device I while that of device II resulted in 1247 cd m-2 and 0.14 cd A-1 respectively.

Geminal cross-coupling synthesis, ion-induced emission and lysosome imaging of cationic tetraarylethene oligoelectrolytes

Neutral conjugated tetraarylethenes OFn (n = 1-3) and the corresponding cationic conjugated oligoelectrolytes OFn+ (n = 1-3) with aggregation-induced emission activity have been designed and synthesized using geminal cross-coupling.

Quenching effects of gold nanoparticles in nanocomposites formed in watersoluble conjugated polymer nanoreactors

In this paper we describe the first example of the in situ synthesis of gold nanoparticles (AuNPs) in the presence of a water-soluble conjugated polyfluorene (NPF) presenting pendent ammonium groups, with the polymer acting as an aqueous surfactant and providing fluorescent nanoreactors. Using this approach, we produced well-dispersed NPF-AuNP nanocomposites without the need for any additional reducing agents. The photoluminescence emission intensity of NPF-AuNP nanocomposite solution was quenched to a greater extent upon increasing the concentration of AuNPs, presumably through energy transfer or electron transfer from the fluorescent polymer to the metal nanoparticles. Through variations in the degrees of protonation and deprotonation of the amino groups of NPF at different values of pH, we found that the extent of quenching of AuNPs in NPF-AuNP nanocomposite solutions was directly related to the adsorption and desorption behavior of NPF on the metal surfaces. Transmission electron microscopy revealed that the greatest aggregation of AuNPs in the nanocomposite solution occurred at pH 3, suggesting that the ammonium groups (RNMe2 at pH 8.5; RNMe2H at pH 3) of the polymer side chains adsorbed onto the AuNP surfaces under these conditions. Distinct time-resolved fluorescence signals of the AuNP-quenched NPF polymers at different values of pH confirmed the interactions between these species.

Multifunctional Probe Based on Cationic Conjugated Polymers for Nitroreductase-Related Analysis: Sensing, Hypoxia Diagnosis, and Imaging

Nitroreductase (NTR) is overexpressed in hypoxic tumors. Moreover, hypoxia is usually considered as the most important feature of various diseases. Thus, it is important to build a sensitive and selective method for NTR detection and hypoxia diagnosis. He