2-trimethylsilyl-9,9-bis(3S,7-dimethyloctyl)fluoren-7-boronic acid | 491880-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-trimethylsilyl-9,9-bis(3S,7-dimethyloctyl)fluoren-7-boronic acid
• 英文别名: 2-trimethylsilyl-9,9-bis(3S,7-dimethyloctyl)-fluoren-7-yl-boronic acid；2-trimethylsilyl-9,9-bis[(S)-3,7-dimethyloctyl]-fluoren-7-yl-boronic acid；[9,9-bis[(3S)-3,7-dimethyloctyl]-7-trimethylsilylfluoren-2-yl]boronic acid
• CAS: 491880-70-7
• 化学式: C₃₆H₅₉BO₂Si
• 分子量: 562.76
• InChiKey: BRCMOZSSZDIXKL-VMPREFPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.66
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-trimethylsilyl-9,9-bis(3S,7-dimethyloctyl)fluoren-7-boronic acid 、 2,7-dibromo-9,9-bis(2-methylbutyl)fluorene 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以89%的产率得到2,7''-ditrimethylsilyl-9,9,9'',9''-tetrakis(3S,7-dimethyloctyl)-9',9'-bis(2-methylbutyl)-7,2';7',2''-terfluorene
  参考文献：
  名称：

  Origin of Strong Chiroptical Activities in Films of Nonafluorenes with a Varying Extent of Pendant Chirality

  摘要：

  Novel nonafluorenes with a varying extent of pendant chirality were synthesized for an investigation of the origins of chiroptical activities in neat films. Thermal annealing of 4-mum-thick sandwiched films and of 90-nm-thick spin-cast films, all on surface-treated substrates, produced monodomain glassy films characterized as a right-handed cholesteric stack with a helical pitch length ranging from 180 to 534 nm and from 252 to 1151 nm, respectively. The observed strong circular dichroism (CD) and g(e) as functions of helical pitch length in single-substrate monodomain glassy cholesteric films were quantitatively interpreted with a circularly polarized fluorescence theory accounting for light absorption, emission, and propagation in a cholesteric stack. Although intertwined molecular helices were likely to be present, cholesteric stacking of rodlike molecules seemed to be the predominant contributor to the strong chiroptical activities. All the cholesteric stacks comprising a polydomain glassy film on an untreated substrate were found to contribute to CD and g(e) largely to the same extent as in a monodomain film. A circularly polarized blue organic light-emitting diode containing a nonafluorene film resulted in a g(e) of 0.35 with a luminance yield of 0.94 cd/A at 20 mA/cm(2), the best performance to date.

  DOI：

  10.1021/ja037733e
• 作为产物：
  描述：

  Br-OF1-Br 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 2-trimethylsilyl-9,9-bis(3S,7-dimethyloctyl)fluoren-7-boronic acid
  参考文献：
  名称：

  单分散手性低聚芴的合成、表征和光学性质

  摘要：

  合成并表征了第一系列单分散手性低聚芴。发现链长在固体形态中起重要作用。二聚体到四聚体是无定形的，而五聚体到十六聚体都表现出胆甾型介晶现象，对结晶具有不同程度的形态稳定性。原始的旋铸薄膜，约 90 nm 厚，是无定形的，但表现出明显的圆二色性和高效的圆偏振荧光，表明手性组件的存在仍有待实验表征。制备了具有两组被 3S,7-二甲基辛基取代的 2S-甲基丁基的九聚体，并且显示能够通过热处理形成单域、玻璃状胆甾醇膜。与非晶质原始膜相比，胆甾醇膜导致圆二色性的数量级增加和圆偏振荧光的旋向性反转。分子动力学模拟为纯薄膜中观察到的手性光学特性的分子起源提供了新的见解。

  DOI：

  10.1021/ja026165k

文献信息

• A convenient synthetic approach to bis-functionalised quaterfluorenes
  作者：Roberto Grisorio、Piero Mastrorilli、Cosimo Francesco Nobile、Giuseppe Romanazzi、Gian Paolo Suranna、E.W Meijer

  DOI：10.1016/j.tetlet.2004.05.074

  日期：2004.7

  esters or trimethylsilyl groups proves to be an efficient method for the preparation of reactive bifluorenes, which are key intermediates for the synthesis of bis-substituted oligofluorenes. The synthetic method has been exploited as a key step for the synthesis of a chiral 2,7‴-diiodo-quaterfluorene and a 2,7‴-bis-amino quaterfluorene.

  Ni（COD）2促进了用硼酸酯或三甲基甲硅烷基官能化的溴芴的偶联，是制备活性双芴的有效方法，而活性双芴是合成双取代低聚芴的关键中间体。该合成方法已被用作合成手性2，7′-二碘-季四芴和2，7′-双氨基-季四芴的关键步骤。
• Synthesis, Characterization, and Optical Properties of Monodisperse Chiral Oligofluorenes
  作者：Yanhou Geng、Anita Trajkovska、Dimitris Katsis、Jane J. Ou、Sean W. Culligan、Shaw H. Chen

  DOI：10.1021/ja026165k

  日期：2002.7.1

  The first series of monodisperse chiral oligofluorenes was synthesized and characterized. Chain length was found to play an important role in solid morphology. Whereas dimer through tetramer are amorphous, pentamer through hexadecamer all show cholesteric mesomorphism with varying degrees of morphological stability against crystallization. Pristine spin-cast films, approximately 90 nm in thickness

  合成并表征了第一系列单分散手性低聚芴。发现链长在固体形态中起重要作用。二聚体到四聚体是无定形的，而五聚体到十六聚体都表现出胆甾型介晶现象，对结晶具有不同程度的形态稳定性。原始的旋铸薄膜，约 90 nm 厚，是无定形的，但表现出明显的圆二色性和高效的圆偏振荧光，表明手性组件的存在仍有待实验表征。制备了具有两组被 3S,7-二甲基辛基取代的 2S-甲基丁基的九聚体，并且显示能够通过热处理形成单域、玻璃状胆甾醇膜。与非晶质原始膜相比，胆甾醇膜导致圆二色性的数量级增加和圆偏振荧光的旋向性反转。分子动力学模拟为纯薄膜中观察到的手性光学特性的分子起源提供了新的见解。
• Origin of Strong Chiroptical Activities in Films of Nonafluorenes with a Varying Extent of Pendant Chirality
  作者：Yanhou Geng、Anita Trajkovska、Sean W. Culligan、Jane J. Ou、H. M. Philip Chen、Dimitris Katsis、Shaw H. Chen

  DOI：10.1021/ja037733e

  日期：2003.11.1

  Novel nonafluorenes with a varying extent of pendant chirality were synthesized for an investigation of the origins of chiroptical activities in neat films. Thermal annealing of 4-mum-thick sandwiched films and of 90-nm-thick spin-cast films, all on surface-treated substrates, produced monodomain glassy films characterized as a right-handed cholesteric stack with a helical pitch length ranging from 180 to 534 nm and from 252 to 1151 nm, respectively. The observed strong circular dichroism (CD) and g(e) as functions of helical pitch length in single-substrate monodomain glassy cholesteric films were quantitatively interpreted with a circularly polarized fluorescence theory accounting for light absorption, emission, and propagation in a cholesteric stack. Although intertwined molecular helices were likely to be present, cholesteric stacking of rodlike molecules seemed to be the predominant contributor to the strong chiroptical activities. All the cholesteric stacks comprising a polydomain glassy film on an untreated substrate were found to contribute to CD and g(e) largely to the same extent as in a monodomain film. A circularly polarized blue organic light-emitting diode containing a nonafluorene film resulted in a g(e) of 0.35 with a luminance yield of 0.94 cd/A at 20 mA/cm(2), the best performance to date.