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(2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE), also known as 2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane), is a chemical compound that serves as a precursor for the synthesis of polymer semiconductors. It is characterized by its unique molecular structure, which includes fluorene and boronate groups, making it a versatile building block for various applications in the field of organic electronics.

196207-58-6

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196207-58-6 Usage

Uses

Used in Organic Electronics Industry:
(2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE) is used as a precursor for the synthesis of polymer semiconductors for the following applications:
1. OLED (Organic Light-Emitting Diode) Applications:
In the OLED industry, (2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE) is used as a key building block for the development of novel materials with improved performance characteristics, such as enhanced brightness, efficiency, and stability. Its incorporation into the polymer semiconductors can lead to better charge transport properties and improved device lifetime.
2. PLED (Polymer Light-Emitting Diode) Applications:
Similar to OLED applications, (2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE) is utilized in the synthesis of polymer semiconductors for PLEDs, where it contributes to the development of materials with superior electrical and optical properties, enabling more efficient and durable light-emitting devices.
3. OFET (Organic Field-Effect Transistor) Applications:
In the OFET industry, (2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE) is used as a precursor for the synthesis of polymer semiconductors that exhibit excellent charge transport properties. These materials are crucial for the development of high-performance organic transistors with improved switching speeds, on-off ratios, and stability.
4. Polymer Solar Cell Applications:
(2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE) is also used in the synthesis of polymer semiconductors for polymer solar cells, where it plays a vital role in enhancing the light absorption and charge separation properties of the active layer. Its incorporation can lead to improved power conversion efficiency and overall device performance.
Additionally, 9,9-Di-n-octylfluorene-2,7-diboronic acid bis(pinacol) ester, a related compound, is used as a reactant in the synthesis of 6,6-(5,5-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(thiophene-5,2-diyl))bis(2,5-bis(2-ethylhexyl)-3-(thiophen-2-yl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione) (DPP1), a solution-processable nonfullerene electron acceptor used in organic solar cells. This highlights the importance of this family of compounds in the development of advanced materials for sustainable energy applications.

Check Digit Verification of cas no

The CAS Registry Mumber 196207-58-6 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,9,6,2,0 and 7 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 196207-58:
(8*1)+(7*9)+(6*6)+(5*2)+(4*0)+(3*7)+(2*5)+(1*8)=156
156 % 10 = 6
So 196207-58-6 is a valid CAS Registry Number.

196207-58-6 Well-known Company Product Price

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  • TCI America

  • (B3582)  2,7-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-di-n-octylfluorene  >98.0%(HPLC)

  • 196207-58-6

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  • 1,570.00CNY

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  • Alfa Aesar

  • (H51955)  9,9-Di-n-octylfluorene-2,7-diboronic acid bis(pinacol) ester, 95%   

  • 196207-58-6

  • 1g

  • 461.0CNY

  • Detail
  • Alfa Aesar

  • (H51955)  9,9-Di-n-octylfluorene-2,7-diboronic acid bis(pinacol) ester, 95%   

  • 196207-58-6

  • 5g

  • 2304.0CNY

  • Detail

196207-58-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-[9,9-dioctyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1.2 Other means of identification

Product number -
Other names 9,9-Dioctyl-9H-fluorene-2,7-diboronic acid bis(pinacol) ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:196207-58-6 SDS

196207-58-6Relevant articles and documents

Synthesis and light-emitting properties of new polyfluorene copolymers containing 2,3-diphenylfumaronitrile

Mi, Dongbo,Kim, Hee Un,Lee, Seon Young,Lee, Jonghee,Hong, Sung-Chul,Pyo, Sungmoon,Hwang, Do-Hoon

, p. 64 - 73 (2010)

A series of polyfluorene copolymers composed of 9,9-dioctylfluorene (DOF) and 2,3-diphenylfumaronitrile (DPFN), poly(DOF-co-DPFN)s, have been synthesized through a palladium (0)-catalyzed Suzuki coupling reaction, and their light-emitting properties have

Deep blue light-emitting polymers with fluorinated backbone for enhanced color purity and efficiency

Zhang, Ting,Wang, Renjie,Ren, Huicai,Chen, Zhiguang,Li, Jiuyan

, p. 1529 - 1534 (2012)

Two fluorene-based copolymers (PF-33F and PF-50F) with p-difluorophenylene units in the backbone were synthesized. In comparison with the reference poly(9,9-dioctylfluorene) (PFO), the introduction of p-difluorophenylene units not only increased the fluorescent quantum yields, but also improved the spectra purity and stability of these deep blue emitting copolymers. The famous green emission band at 520 nm from fluorenone defects was never detected for these copolymers even after they were thermal annealed in air at 150 °C. Organic light-emitting diodes were fabricated using them as emitting layer and pure blue electroluminescence was obtained. It was observed that PF-33F based device exhibited much higher current density and brightness than PF-50F and PFO devices. A maximum external quantum efficiency of 1.14% (1.14 cd A-1) and the CIE (0.16, 0.13) were achieved for PF-33F device, which are among the best performance for polyfluorenes reported so far.

Effect of Arylmethylene Substitutions on Molecular Structure, Optoelectronic Properties and Photovoltaic Performance of Dithienocyclopentafluorene-Based Small-Molecule Acceptors

Tang, Xuejiao,Liao, Haitao,Zheng, Tao,Yin, Pan,Cao, Jing,Zeng, Xiaoying,Weng, Chao,Shen, Ping

, p. 14508 - 14519 (2021)

Two dithienocyclopentafluorene-based small-molecule acceptors (SMAs) were developed that feature methylene-functionalized conjugated side chains, to study the effect of arylmethylene substitution and its number on structure, optoelectronic properties and device performance. Results showed that two SMAs have better absorption properties and planarity, lower bandgaps and higher LUMOs compared with the control SMA without conjugated side chains. The synthesized SMAs were tested in polymer solar cells for examples of their applicability. This work argues that the introduction of methylene-functionalized conjugated side chains has great potential in tuning molecular structure, optoelectronic properties, device physics and photovoltaic performance of SMAs.

Achieving highly efficient blue light-emitting polymers by incorporating a styrylarylene amine unit

Peng, Feng,Zhong, Zhiming,Ma, Yawei,Huang, Zhenqiang,Ying, Lei,Xiong, Jian,Wang, Shirong,Li, Xianggao,Peng, Junbiao,Cao, Yong

, p. 12355 - 12363 (2018)

A series of novel blue light-emitting polymers were designed and synthesized by incorporating a blue styrylarylene amine (DV) chromophore into the backbone of poly(9,9-dioctylfluorene). All the resultant polymers exhibit blue emission peaking at around 46

Tunable Control of the Hydrophilicity and Wettability of Conjugated Polymers by a Postpolymerization Modification Approach

Cong, Shengyu,Creamer, Adam,Fei, Zhuping,Hillman, Sam A. J.,Rapley, Charlotte,Nelson, Jenny,Heeney, Martin

, (2020)

A facile method to prepare hydrophilic polymers by a postpolymerization nucleophillic aromatic substitution reaction of fluoride on an emissive conjugated polymer (CP) backbone is reported. Quantitative functionalization by a series of monofunctionalized ethylene glycol oligomers, from dimer to hexamer, as well as with high molecular weight polyethylene glycol is demonstrated. The length of the ethylene glycol sidechains is shown to have a direct impact on the surface wettability of the polymer, as well as its solubility in polar solvents. However, the energetics and band gap of the CPs remain essentially constant. This method therefore allows an easy way to modulate the wettability and solubility of CP materials for a diverse series of applications.

Electroluminescent poly(fluorene-co-thiophene-S,S-dioxide): Synthesis, characterisation and structure-property relationships

Pasini, Mariacecilia,Destri, Silvia,Porzio, William,Botta, Chiara,Giovanella, Umberto

, p. 807 - 813 (2003)

A new copolymer, constituted by the regular alternation of a fluorene derivative with a 1,1-dioxothiophene moiety, has been synthesised via Suzuki coupling. The molecular, thermal, structural, and photophysical characterisations have been performed. The material showed two dimensional order, enhanced by annealing; molecular modelling calculations afforded a consistent structural model accounting for the optical data. In comparison with both polyfluorenes and 1,1-dioxothiophene oligomers the unusual photoluminescence quantum yields observed in solution and in the solid state can be related to a significant contribution of internal conversion to the deactivation process in solution, and the formation of intra-chain hydrogen-bonds, due to a peculiar chain conformation, in the solid state. LED devices based on this new copolymer showed the highest efficiency compared with similar copolymers containing both fluorene and 1,1-dioxothiophene functionalities.

Thieno[3,2-b]thiophene-based conjugated polyfluorene copolymer for efficient polymer solar cell

Kim, Joo Yeon,Kim, Hye-Min,Lee, Ja-Eun,Kim, Tae-Dong,Baek, Nam Seob

, p. 6331 - 6336 (2014)

We have synthesized and characterized a polyfluorene derivative composed of octyl-substituted thieno[3,2,-b]thiophene and 2,1,3-benzothiadiazole as an acceptor unit. The best power conversion efficiencies of the polymer were showed with 1.63% and 2.31% by using PCBM and PC71BM, respectively. Copyright

Synthesis and optical and electroluminescent properties of novel conjugated copolymers derived from fluorene and benzoselenadiazole

Yang, Renqiang,Tian, Renyu,Hou, Qiong,Yang, Wei,Cao, Yong

, p. 7453 - 7460 (2003)

A novel series of light-emitting copolymers derived from 9,9-dioctylfluorene (DOF) and 2,1,3-benzoselenadiazole (BSeD) is prepared by means of palladium-catalyzed Suzuki coupling reaction. The feed ratios of DOF to BSeD were 50:50, 85:15, 92:8, and 98:2, respectively. All of the copolymers are soluble in common organic solvents and highly fluorescent in solid state. Devices from such copolymers emit orange-red light with λmax = 570-600 nm. The maximal EL emissions of the devices slightly red-shifted gradually with increasing BSeD's contents. The maximal external quantum efficiency of the polymer light-emitting devices (PLED) reaches 1.0%, which indicates that this new seleno-containing EL polymer based on fluorene and benzoselenadiazole is a promising candidate for fabricating PLEDs.

4-hexylbithieno[3,2-b:2′3′-e]pyridine: An efficient electron-accepting unit in fluorene and indenofluorene copolymers for light-emitting devices

Sonar, Prashant,Zhang, Jingying,Grimsdale, Andrew C.,Müllen, Klaus,Surin, Mathieu,Lazzaroni, Roberto,Leclère, Philippe,Tierney, Steve,Heeney, Martin,McCulloch, Iain

, p. 709 - 715 (2004)

4-Hexylbithienopyridine has been prepared as a novel electron-accepting monomer for conjugated polymers. To test its electronic properties, alternating copolymers with fluorene and indenofluorene polymers have been prepared. The copolymers displayed reduction potentials about 0.5 V lower than for the corresponding fluorene and indenofluorene homopolymers, indicating much improved electron-accepting properties. Analysis of the microscopic morphology of thin films of the copolymers by AFM shows that they lack the extensive supramolecular order seen with the homopolymers, which is attributed to the bithienopyridine units disrupting the π-stacking. LEDs using these polymers as the emitting layer produce blue-green emission with low turn-on voltages with aluminum electrodes confirming their improved electron affinity. The indenofluorene copolymer displayed an irreversible red shift in emission at high voltages, which is attributed to oxidation of the indenofluorene units. This red shift occurred at higher potentials than for indenofluorene homopolymers in LEDs, suggesting that the heterocyclic moieties offer some protection against electrically promoted oxidation.

High-Efficiency Saturated Red Emitting Polymers Derived from Fluorene and Naphthoselenadiazole

Yang, Jian,Jiang, Changyun,Zhang, Yong,Yang, Renqiang,Yang, Wei,Hou, Qiong,Cao, Yong

, p. 1211 - 1218 (2004)

A variety of novel light-emitting copolymers derived from 9,9-dioctylfluorene (DOF) and 2,1,3-naphthozoselenadiazole (NSeD) were prepared by the palladium-catalyzed Suzuki coupling reaction. The feed ratios of DOF to NSeD were 99.9:0.1, 99.5:0.5, 99:1, 98:2, 95:5, and 85:15. All of the polymers are soluble in common organic solvents and highly fluorescent in solid state. Devices based on the copolymers emit saturated red light, and the emission slightly red-shifted gradually with increasing NSeD's contents. The maximal external quantum efficiency of the polymer light-emitting devices (PLED) reaches 3.1%, and luminous efficiency is greater than 1.0 cd/A with emission maximum at 657 nm and Commission Internationale de L'Eclairage (CIE) coordinates of (0.64, 0.33). This is the highest efficiency with saturated red emission for a single-layer device with nonblend type emitter reported so far in the scientific literature. This indicates that the new EL polymers based on fluorene and naphthoselenadiazole are promising as a red emitter in polymer light-emitting displays.

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