(2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE)

Base Information

• Chemical Name: (2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE)
• CAS No.: 196207-58-6
• Molecular Formula: C41H64B2O4
• Molecular Weight: 642.579
• Hs Code.: 29319090
• Mol file: 196207-58-6.mol

Synonyms:(2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE)

Chemical Property of (2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE)

Chemical Property:

• Melting Point: 129 °C
• Boiling Point: 701.622 °C at 760 mmHg
• Flash Point: 378.127 °C
• PSA: 36.92000
• Density: 1.019 g/cm³
• LogP: 10.05270
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Slightly soluble in water.

Purity/Quality:

98% ^*data from raw suppliers

9,9-Dioctylfluorene-2,7-diboronicAcidbis(Pinacol)Ester ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Description: 2,2'-(9,9-dioctyl-9H-fluorene-2,7-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) is a precursor for the synthesis of polymer semiconductors in the application of OLED, PLED, OFET and Polymer Solar Cells.
• Uses: 9,9-Di-n-octylfluorene-2,7-diboronic acid bis(pinacol) ester is 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.

Technology Process of (2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE)

There total 10 articles about (2,7-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-9,9-DIOCTYLFLUORENE) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 2,7-dibromo-9,9-dioctylfluorene (198964-46-4) → 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (196207-58-6)

Guidance literature:

2,7-dibromo-9,9-dioctylfluorene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 0.616667h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 30h;

DOI:10.1039/b208742a

Reference yield: 91.0%

bis(pinacol)diborane (73183-34-3) + 2,7-dibromo-9,9-dioctylfluorene (198964-46-4) → 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (196207-58-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; Inert atmosphere;

Reference yield: 90.0%

→ 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (196207-58-6)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; for 16h; Inert atmosphere; Reflux;

upstream raw materials:

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

2,7-dibromo-9,9-dioctylfluorene

2-isopropyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

9H-fluorene

Downstream raw materials:

2,7-bis(4-phenylcarboxylic acid methyl ester)-9,9-di-n-octylfluorene

2,7-bis(4-phenylcarboxylic acid)-9,9-di-n-octylfluorene

Refernces

• 1、 Zhang, Ting,Wang, Renjie,Ren, Huicai,Chen, Zhiguang,Li, Jiuyan. "Deep blue light-emitting polymers with fluorinated backbone for enhanced color purity and efficiency". . p. 1529 - 1534. Retrieved 2012.
• 2、 Peng, Feng,Zhong, Zhiming,Ma, Yawei,Huang, Zhenqiang,Ying, Lei,Xiong, Jian,Wang, Shirong,Li, Xianggao,Peng, Junbiao,Cao, Yong. "Achieving highly efficient blue light-emitting polymers by incorporating a styrylarylene amine unit". . p. 12355 - 12363. Retrieved 2018.
• 3、 Pasini, Mariacecilia,Destri, Silvia,Porzio, William,Botta, Chiara,Giovanella, Umberto. "Electroluminescent poly(fluorene-co-thiophene-S,S-dioxide): Synthesis, characterisation and structure-property relationships". . p. 807 - 813. Retrieved 2003.
• 4、 Yang, Renqiang,Tian, Renyu,Hou, Qiong,Yang, Wei,Cao, Yong. "Synthesis and optical and electroluminescent properties of novel conjugated copolymers derived from fluorene and benzoselenadiazole". . p. 7453 - 7460. Retrieved 2003.
• 5、 Yang, Jian,Jiang, Changyun,Zhang, Yong,Yang, Renqiang,Yang, Wei,Hou, Qiong,Cao, Yong. "High-Efficiency Saturated Red Emitting Polymers Derived from Fluorene and Naphthoselenadiazole". . p. 1211 - 1218. Retrieved 2004.
• 6、 Lv, Wei,Liu, Huijiao,Wang, Wen,Yang,Zhen, Hongyu,Ling, Qidan. "Synthesis of new conjugated polymers with coordinated praseodymium complexes for polymer memory devices". . p. 18384 - 18391. Retrieved 2017.
• 7、 He, Keqi,Wang, Xiangdong,Yu, Junting,Jiang, Haigang,Xie, Guangshan,Tan, Hua,Liu, Yu,Ma, Dongge,Wang, Yafei,Zhu, Weiguo. "Synthesis and optoelectronic properties of novel fluorene-bridged dinuclear cyclometalated iridium (III) complex with A-D-A framework in the single-emissive-layer WOLEDs". . p. 2942 - 2949. Retrieved 2014.
• 8、 Zhang, Xingye,Cao, Shilin,Huang, Liulian,Chen, Lihui,Ouyang, Xinhua. "Enhanced three-photon absorption and excited up-conversion fluorescence of phenanthroimidazole derivatives". . p. 110 - 115. Retrieved 2017.
• 9、 Jung, In Hwan,Kim, Sun Hee,Jeong, Eunjae,Yang, Renqiang,Lee, Kwanghee,Woo, Han Young,Shim, Hong-Ku. "Synthesis and characterization of fluorene and cyclopentadithiophene-based copolymers exhibiting broad absorption for photovoltaic devices". . p. 1248 - 1255. Retrieved 2011.
• 10、 Lim, Eunhee,Jung, Byung-Jun,Shim, Hong-Ku. "Synthesis and characterization of a new light-emitting fluorene-thieno[3,2-b]thiophene-based conjugated copolymer". . p. 4288 - 4293. Retrieved 2003.