380600-91-9

Usage

Uses

Used in Organic Semiconductors:
9,9-Di-n-octylfluorene-2,7-dicarboxaldehyde serves as a crucial building block in the synthesis of organic semiconductors, which are key components in various electronic devices. Its role in this application is attributed to its ability to enhance the performance and stability of the semiconductors.
Used in Light-Emitting Materials:
In the field of optoelectronics, 9,9-Di-n-octylfluorene-2,7-dicarboxaldehyde is utilized in the creation of light-emitting materials, particularly for organic light-emitting diodes (OLEDs). Its chemical structure allows for efficient light emission, making it a valuable asset in the development of high-quality OLEDs.
Used in Electronic Devices:
9,9-Di-n-octylfluorene-2,7-dicarboxaldehyde is employed in the fabrication of electronic devices such as field-effect transistors. Its incorporation into these devices contributes to improved device performance and reliability, underpinning its significance in advancing electronic technology.
Used in Advanced Material Development:
The unique properties of 9,9-Di-n-octylfluorene-2,7-dicarboxaldehyde make it a promising candidate for the development of advanced materials tailored for specific electronic applications. Its versatility and compatibility with other materials facilitate the creation of innovative solutions in the electronics industry.

Upstream product

• 68-12-2 N,N-dimethyl-formamide 
• 198964-46-4 2,7-dibromo-9,9-dioctylfluorene 
• 222159-97-9 (9,9-dioctyl-9H-fluorene-2,7-diyl)dimethanol 
• 16433-88-8 2,7-dibromo-9H-fluorene 
• 86-73-7 9H-fluorene 
• 111-83-1 1-bromo-octane 

Downstream Products

• 1334306-18-1 (E)-7-(4-(diphenylamino)styryl)-9,9-dioctyl-9H-fluorene-2-carbaldehyde 

Relevant academic research and scientific papers

Synthesis and characterization of poly(9,9-dialkylfluorenevinylene benzobisoxazoles): New solution-processable electron-accepting conjugated polymers

We present the synthesis of four new solution-processable, fluorescent poly(arylenevinylene)s containing benzobisoxazole and fluorene moieties. Two different moieties (cis- and trans-benzobisoxazole) and two different alkyl substituents (octyl and 3,7-dimethyloctyl) were used to study the impact of the structure on the electronic, optical, and thermal properties of these polymers. The polymers were characterized using UV - visible and fluorescence spectroscopy, cyclic voltammetry, thermal gravimetric analysis (TGA), and differential scanning calorimetry (DSC). All of the polymers possess moderate molecular weights, good solubility in aprotic organic solvents, high fluorescence quantum efficiencies in dilute solutions, and high electron affinities. Cyclic voltammetry revealed quasi-reversible reduction for these polymers. Solution-processed light-emitting diodes using dilute blends of the polymer in a poly(N-vinyl carbazole) matrix gave blue emission with luminous efficiencies of up to 1 Cd/A at ～470 nm which is very promising for deep blue-emitting polymer LEDs.

Synthesis of Conjugated Copolymer Containing Spirobifluorene Skeleton by Acyclic Diene Metathesis Polymerization for Polymer Light-Emitting Diode Applications

Grubbs-type, Hoveyda-type, cyclic alkyl amino carbene (CAAC)-based ruthenium olefin metathesis catalysts were used for the acyclic diene metathesis (ADMET) polymerization of 2,7-divinyl-9,9-di-n-octylfluorene (DVF). Additionally, various ratios of DVF and 2,2′,7,7′-tetravinyl-9,9′-spirobifluorene (TVSF) were subjected to ADMET polymerization to obtain polymers P1–P7. Polymers P1–P4 were analyzed with gel permeation chromatography, UV–vis spectroscopy, and photoluminescence spectroscopy. As the TVSF ratio increases, polymers exhibit lower solubility but a narrower band in the photoluminescence spectrum. Polymer light-emitting diode (PLED) devices were fabricated with polymers P1, P2, and P3. The performances of the PLED devices indicated that polymers including more spirobifluorene blocks showed better turn-on voltage, brightness, current efficiency, and power efficiency.

Quinoid compounds and preparation method and applications thereof

Quinoid compounds and a preparation method and applications thereof are disclosed. The general structure of the compounds is shown in the description. The structures of the compounds can be easily modified, and the compounds have characteristics of good molecular skeleton planarity, high self-assembling capability, low energy level of the highest unoccupied orbit (LUMO), narrow band gaps, and insensitivity to water and oxygen, and therefore the compounds as organic semiconductor materials can greatly improve hole and electron transmission capability so that the compounds are applied as n type(electron transmitting) materials and bipolar materials (capable of transmitting holes and electrons) into organic field effect transistors, organic solar cells, perovskite solar cells, organic thermoelectric and organic light-emitting devices, and the like.

Synthesis and ring opening reaction of octaoctyl substituted [2.2.2.2](2,7)-fluorenophanetetraene by photooxidation

Octaoctyl substituted fluorenophanetetraene has been synthesized from its corresponding octaoctyl substituted tetrathia[3.3.3.3]fluorenophane followed by benzyne Stevens rearrangement, oxidation and thermal elimination. The solid-state structure of octaoctyl substituted [2.2.2.2](2,7)-fluorenophanetetraene reveals that fluorene units are connected by cis vinylenes and alkyl chains are located inside and outside the rings. The photooxidation reaction of the fluorenophanetetraene was carried out in a dilute solution under UV light irradiation to give all trans linear fluorenevinylene with aldehyde end groups. The optical properties of the fluorenophanetetraene and its linear compound generated by photooxidation have been investigated and compared. The fluorescence quantum yield of the fluorenophanetetraene in solution is much lower than that of its linear compound generated by photooxidation due to shorter effective conjugation lengths; however, the fluorescence intensity of the fluorenophanetetraene in the solid state is much higher than that of its linear compound generated by photooxidation possibly due to weak intermolecular interaction.

COMPOUND FOR ORGANIC PHOTOELECTRIC DEVICE AND ORGANIC PHOTOELECTRIC DEVICE IMAGE SENSOR, AND ELECTRONIC DEVICE INCLUDING THE SAME

A compound for an organic photoelectric device includes at least one of a compound represented by Chemical Formula 1, a compound represented by Chemical Formula 2 and a combination thereof.

Does a cyclopropane ring enhance the electronic communication in dumbbell-type C60 dimers?

Two C60 dumbbell molecules have been synthesized containing either cyclopropane or pyrrolidine rings connecting two fullerenes to a central fluorene core. A combination of spectroscopic techniques reveals that the cyclopropane dumbbell possesses better electronic communication between the fullerenes and the fluorene. This observation is underpinned by DFT transport calculations, which show that the cyclopropane dumbbell gives a higher calculated single-molecule conductance, a result of an energetically lower-lying LUMO level that extends deeper into the backbone. This strengthens the idea that cyclopropane behaves as a quasi-double bond.

Synthesis, characterization, and electroluminescence properties of poly(fluorenevinylene benzobisthiazoles)

A series of vinylene-linked copolymers based on electron-deficient benzobisthiazole and electron-rich fluorene moieties were synthesized via Horner-Wadsworth-Emmons polymerization. Three different polymers P1, P2, and P3, were prepared bearing octyl, 3,7-dimethyloctyl, and 2-(2-ethoxy)ethoxyethyl side chains, respectively. The polymers all possessed moderate molecular weights, good solubility in aprotic organic solvents, and high fluorescence quantum efficiencies in dilute solutions. P2, which bore branched 3,7-dimethyloctyl side chains, exhibited better solubility than the other polymers, but also exhibited the lowest thermal decomposition temperature of all polymers. Overall, the impact of the side chains on the polymers optical properties in solution was negligible as all three polymers gave similar absorption and emission spectra in both solution and film. Guest-host light-emitting diodes using dilute blends of the polymers in a poly(N-vinylcarbazole) host gave blue-green emission with P2 exhibiting the highest luminous efficiency, 0.61 Cd/A at ～500 nm.

A low band gap donor-acceptor copolymer containing fluorene and benzothiadiazole units: Synthesis and photovoltaic properties

A new low band gap copolymer containing dialkylfluorene and 4,7-dithienyl-2,1,3-benzothiadiazole (TBT), poly(fluorenevinylene-alt-4,7- dithienyl-2,1,3-benzothiadiazole) (PF-TBT) was synthesized by Heck cross-coupling polymerization. The copolymer is soluble in common organic solvents such as chloroform, tetrahydrofuran and chlorobenzene. The TGA result indicated that the copolymer possesses good thermal stability. The absorption, electrochemical and photovoltaic properties of PF-TBT were investigated and compared with those of poly(fluorenevinylene-alt-4,7-diphenyl-2,1,3- benzothiadiazole) (PF-DBT) whose structure is similar to PF-TBT. The copolymer exhibited a broad absorption band with an absorption edge close to 700 nm and an optical band gap of 1.82 eV. Cyclic voltammetry studies indicated that the relatively low HOMO energy level assured a higher open circuit voltage (V oc) when PF-TBT is used as the donor material in a photovoltaic cell. The bulk heterojunction (BHJ) solar cell using PF-TBT as the donor and [6,6]-phenyl C61-butyric acid methyl ester (PCBM) as the acceptor with the structure of ITO/PEDOT:PSS/copolymer:PCBM/LiF/Al, exhibited a Voc of 0.86 V, short-circuit current density (Jsc) of 3.97 mA cm -2, fill factor (FF) of 0.35, and a power conversion efficiency (PCE) of 1.18% under one sun of AM 1.5 solar simulator illumination (100 mW cm -2).

Transition-metal-free synthesis of conjugated polymers from bis-grignard reagents by using TEMPO as Oxidant

(Figure Presented) Increasing the TEMPO! Transition metals are not necessary for oxidative polymerization of 2,7-di-magnesated fluorenes. Oxidation readily occurs by using the commercially available 2,2,6,6-tetramethyl-piperine 1 -oxyl radical (TEMPO) as

Understanding the reversible anodic behaviour and fluorescence properties of fluorenylazomethines A structure-property study

A series of fluorenylazomethine dyads and triads were prepared by simple condensation between the corresponding amine and aldehyde fluorene derivatives. These compounds were prepared as model compounds for investigating the effects of substitution and electronic groups on both the electrochemical properties and fluorescence quantum yields. It was found that the oxidation potential could be decreased by both incorporating electron donating groups and increasing the degree of conjugation. It was further found that alkylation in the fluorene's 9-position increased the azomethine degree of conjugation by forcing all the fluorene moieties to be coplanar with the azomethine bonds to which they are attached. Meanwhile, reversible radical cation behaviour was possible by substituting the terminal 2,2′-positions with atoms other than hydrogen. The radical cation was theoretically found to be distributed evenly across the fluorene, corroborating the reversible anodic behaviour with 2,2′-substitution. The fluorescence quantum yields of the azomethines were not found to be dependent on substitution. This was because the azomethine fluorescence was found to be quenched relative to their precursors regardless of substitution. The fluorescence could be restored at both low temperature and by acid protonation.