2-[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]-4,4,5,5-tetra-methyl[1,3,2]dioxaborolane | 1056044-57-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]-4,4,5,5-tetra-methyl[1,3,2]dioxaborolane
• 英文别名: 2-[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane；2-[9,9-Bis(3-methylbutyl)fluoren-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1056044-57-5
• 化学式: C₂₉H₄₁BO₂
• 分子量: 432.454
• InChiKey: NLZVUPBYMVMESS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-溴芘 、 2-[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]-4,4,5,5-tetra-methyl[1,3,2]dioxaborolane 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 以75%的产率得到1-(9,9-bis(3-methylbutyl)-9H-fluoren-2-yl)pyrene
  参考文献：
  名称：

  Synthesis and Fluorescence Emission Properties of 1,3,6,8-Tetrakis(9H-Fluoren-2-yl)Pyrene Derivative

  摘要：

  通过 1,3,6,8 四溴芘与 2-[9,9-双(3-甲基丁基)-9H-芴-2-基]-4,4,5,5-四甲基[1,3,2]二氧硼戊环的钯催化铃木偶联反应，成功合成了 1,3,6,8 四[9,9-双(3-甲基丁基)-9H-芴-2-基]芘。对这种芘的光特性进行了详细的研究，这些数据表明它有可能用作有机发光二极管中的蓝色发光材料。

  DOI：

  10.3184/030823410x12743772163259
• 作为产物：
  描述：

  频哪醇 、 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 2-[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]-4,4,5,5-tetra-methyl[1,3,2]dioxaborolane
  参考文献：
  名称：

  Synthesis and Fluorescence Emission Properties of 1,3,6,8-Tetrakis(9H-Fluoren-2-yl)Pyrene Derivative

  摘要：

  通过 1,3,6,8 四溴芘与 2-[9,9-双(3-甲基丁基)-9H-芴-2-基]-4,4,5,5-四甲基[1,3,2]二氧硼戊环的钯催化铃木偶联反应，成功合成了 1,3,6,8 四[9,9-双(3-甲基丁基)-9H-芴-2-基]芘。对这种芘的光特性进行了详细的研究，这些数据表明它有可能用作有机发光二极管中的蓝色发光材料。

  DOI：

  10.3184/030823410x12743772163259

文献信息

• Synthesis and fluorescence emission properties of 1,3,6,8-tetraarylpyrenes
  作者：Jian-Yong Hu、Xing Feng、Hirotsugu Tomiyasu、Nobuyuki Seto、Ummey Rayhan、Mark R.J. Elsegood、Carl Redshaw、Takehiko Yamato

  DOI：10.1016/j.molstruc.2013.04.074

  日期：2013.9

  Three types of stable pyrene-based highly fluorescence (blue) compounds, 1-, 1,6-bis, 1,8-bis and 1,3,6,8-tetrakis(7-tert-butylpyrenyl)pyrenes and 1,3,6,8-tetrakis[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]pyrene, were successfully synthesized via a Pd/Cu-catalysed Suzuki cross-coupling reaction of the corresponding bromopyrenes with 7-tert-butyl-1-pyrenylboronic ester or 2[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane, respectively. All compounds have good solubility in common organic solvents and high thermal stability with melting points up to 270 degrees C; the exceptions are the isomeric 1,6-bis-, and 1,8-bispyrenyl-substituted pyrenes. All products show high extinction coefficients of absorption (lambda(max)approximate to 349-396 nm) and high quantum yields (lambda(max)approximate to 432-465 nm; Phi(f)approximate to 0.75-0.99) in dichloromethane solution, and emit strong fluorescence in the visible region ranging from deep-blue to pure-blue on increasing the number of substituents. This data suggests that such systems have promise as blue emitters in organic light-emitting device (OLED) applications (OLED = organic light emitting diode). Crystal structures were determined for 1,3,6,8-tetrakis [9,9-bis(3-methylbutyl)-9H-fluoren-2-yl] pyrene and 1,3,6,8-tetrakis(4-methoxyphenyl)pyrene. (C) 2013 Elsevier B.V. All rights reserved.
• Synthesis and Fluorescence Emission Properties of 1,3,6,8-Tetrakis(9H-Fluoren-2-yl)Pyrene Derivative
  作者：Jian-yong Hu、Hidetaka Hiyoshi、Jung-Hee Do、Takehiko Yamato

  DOI：10.3184/030823410x12743772163259

  日期：2010.5

  A novel pyrene-based highly pure blue fluorescent and stable molecule, 1,3,6,8-tetrakis[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]pyrene, was successfully synthesised via a Pd-catalysed Suzuki coupling reaction of 1,3,6,8-tetrabromo-pyrene with 2-[9,9-bis(3-methylbutyl)-9H-fluoren-2-yl]-4,4,5,5-tetramethyl[1,3,2]dioxaborolane. The photoproperties of this pyrene were examined in detail and these data indicated its potential application as blue-emitting materials in organic light-emitting diodes.

  通过 1,3,6,8 四溴芘与 2-[9,9-双(3-甲基丁基)-9H-芴-2-基]-4,4,5,5-四甲基[1,3,2]二氧硼戊环的钯催化铃木偶联反应，成功合成了 1,3,6,8 四[9,9-双(3-甲基丁基)-9H-芴-2-基]芘。对这种芘的光特性进行了详细的研究，这些数据表明它有可能用作有机发光二极管中的蓝色发光材料。
• Influence of substituent position on thermal properties, photoluminescence and morphology of pyrene–fluorene derivatives
  作者：Xing Feng、Jian-Yong Hu、Xian-Fu Wei、Carl Redshaw、Takehiko Yamato

  DOI：10.1016/j.molstruc.2015.01.018

  日期：2015.4

  New position-dependent conjugated hydrocarbon dyes containing a pyrene core and multi-fluorene moieties 3 have been synthesized and characterized by H-1/C-13 NMR spectroscopy, as well as by optical and theoretical studies. The solubility of mono-, bis- and tetra-fluorenyl-pyrene 3 tends to decrease and leads to varied thermal properties. The results of the optical studies and DFT calculations revealed that the energy gap can be easily modified or fine-tuned by either varying the substituent number or position. Remarkably, such pyrene-fluorene materials exhibited deep blue fluorescence (lambda(max) = 400-458 nm in CH2Cl2) with excellent quantum yields (approximate to 78%). These results suggest that these new pyrene-fluorene derivatives have potential application in OLED technology as blue host materials. (C) 2015 Elsevier B.V. All rights reserved.