2,6-dibromo-9,10-bis(2-phenylethynyl)anthracene | 1192182-18-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,6-dibromo-9,10-bis(2-phenylethynyl)anthracene
• 英文别名: 2,6-dibromo-9,10-bis(phenylethynyl)anthracene；2,6-Dibromo-9,10-bis(2-phenylethynyl)anthracene
• CAS: 1192182-18-5
• 化学式: C₃₀H₁₆Br₂
• 分子量: 536.265
• InChiKey: PDOHQCQMLBSSGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.32
• 重原子数：
  32.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  2,6-dibromo-9,10-bis(2-phenylethynyl)anthracene 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 6-(5-((6-((5-hexylthiophen-2-yl)ethynyl)-9,10-bis(phenylethynyl)-anthracen-2-yl)ethynyl) thiophen-2-yl)hexan-1-ol
  参考文献：
  名称：

  Self-Assembled Monolayers Made of 6-(5-((6-((5-hexylthiophen-2-yl)ethynyl)-9,10-bis(phenylethynyl)anthracen-2-yl)ethynyl)thiophen-2-yl)hexyl 3-(Triethoxysilyl)Propylcarbamate for Ultrathin Film Transistors

  摘要：

  A new functionalized triethoxysilane bearing an X-shaped, anthracene-based semiconducting molecule on one arm was designed and synthesized as a precursor for the preparation of a self-assembled monolayer (SAM) on a SiO2 substrate. 3-Isocyanatopropyl triethoxysilane was reacted with a monohydroxyl-terminated X-shaped, anthracene-based semiconducting molecule in the presence of tin catalyst. The 6-(5( (6- ( (5-hexylthiophen-2-yOethyny1)-9,10-bis (ph enylethyny1)anthracen-2-yOethynypthiophen-2-yOhexyl 3-(triethoxysily1)propylcarbamate (BATHT-TEOS) was found to be stable and sufficiently reactive to form organic monolayers on hydroxylated SiO2 surfaces. The structures and properties of these SAMs were investigated using X-ray photoelectron spectroscopy, UV vis absorption spectroscopy, photoluminescence (PL) spectroscopy, laser scanning confocal microscopy PL spectrometry, and spectroscopic ellipsometry. In this work, BATHT-SAM was employed as an interfacial layer on SiO2 to fabricate ultrathin film transistors (UTFTs, active layer thickness 16.09 nm). The device UTFT-I, made of 0.06 wt % S,S'-(9,10-bis(phenylethynyl)anthracene-2,6-diy1)bis(ethyne-2,1-diyObis(2hexylthiophene) (BATHT) solution on an n-octyltrichlorosilane-SAM/Si02 layer, showed no gate effect for the carrier transport behavior; however, the device UTFT-II, fabricated on BATHT-SAM/Si02, exhibited field effect mobilities of 0.04 cm2 Nr1 s (10,off 6.3 x 103 to 1.0 x 104). This can be attributed to the effect of BATHT-SAM inducing uniform coverage and ordering of BATHT molecules as an upper layer.

  DOI：

  10.1021/la3020942
• 作为产物：
  描述：

  2,6-二溴蒽醌 、 苯乙炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.75h， 以68%的产率得到2,6-dibromo-9,10-bis(2-phenylethynyl)anthracene
  参考文献：
  名称：

  High-mobility anthracene-based X-shaped conjugated molecules for thin film transistors

  摘要：

  新型基于蒽的X形共轭分子1和2被开发为高溶解度的p型有机半导体，并在器件中分别展示了0.04 cm²V⁻¹ s⁻¹（Ion/Ioff = 2.8 × 10⁵）和0.24 cm²V⁻¹ s⁻¹（Ion/Ioff = 5.4 × 10⁶）的大场效应迁移率。

  DOI：

  10.1039/b911780f

文献信息

• [EN] MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES<br/>[FR] MATÉRIAUX POUR DISPOSITIFS ÉLECTROLUMINESCENTS ORGANIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2021110741A1

  公开（公告）日：2021-06-10

  The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to organic electroluminescent devices which comprise these compounds.

  本发明涉及适用于电子器件，特别是有机电致发光器件的化合物（1）的公式，以及包含这些化合物的有机电致发光器件。
• High-mobility anthracene-based X-shaped conjugated molecules for thin film transistors
  作者：Ki Hwa Jung、Suk Young Bae、Kyung Hwan Kim、Min Ju Cho、Kwangyeol Lee、Zee Hwan Kim、Dong Hoon Choi、Dong Hoon Lee、Dae Sung Chung、Chan Eon Park

  DOI：10.1039/b911780f

  日期：——

  New anthracene-based X-shaped conjugated molecules 1 and 2 for use as highly soluble p-type organic semiconductors were developed and exhibited large field-effect mobilities of 0.04 cm2V−1 s−1 (Ion/Ioff = 2.8 × 105) and 0.24 cm2V−1 s−1 (Ion/Ioff = 5.4 × 106) for devices of 1 and 2, respectively.

  新型基于蒽的X形共轭分子1和2被开发为高溶解度的p型有机半导体，并在器件中分别展示了0.04 cm²V⁻¹ s⁻¹（Ion/Ioff = 2.8 × 10⁵）和0.24 cm²V⁻¹ s⁻¹（Ion/Ioff = 5.4 × 10⁶）的大场效应迁移率。
• Self-Assembled Monolayers Made of 6-(5-((6-((5-hexylthiophen-2-yl)ethynyl)-9,10-bis(phenylethynyl)anthracen-2-yl)ethynyl)thiophen-2-yl)hexyl 3-(Triethoxysilyl)Propylcarbamate for Ultrathin Film Transistors
  作者：Dong Uk Heo、Joo Bin Lee、Yoon Deok Han、Jinsoo Joo、Hosuk Lee、Hosun Lee、Dong Hoon Choi

  DOI：10.1021/la3020942

  日期：2012.7.24

  A new functionalized triethoxysilane bearing an X-shaped, anthracene-based semiconducting molecule on one arm was designed and synthesized as a precursor for the preparation of a self-assembled monolayer (SAM) on a SiO2 substrate. 3-Isocyanatopropyl triethoxysilane was reacted with a monohydroxyl-terminated X-shaped, anthracene-based semiconducting molecule in the presence of tin catalyst. The 6-(5( (6- ( (5-hexylthiophen-2-yOethyny1)-9,10-bis (ph enylethyny1)anthracen-2-yOethynypthiophen-2-yOhexyl 3-(triethoxysily1)propylcarbamate (BATHT-TEOS) was found to be stable and sufficiently reactive to form organic monolayers on hydroxylated SiO2 surfaces. The structures and properties of these SAMs were investigated using X-ray photoelectron spectroscopy, UV vis absorption spectroscopy, photoluminescence (PL) spectroscopy, laser scanning confocal microscopy PL spectrometry, and spectroscopic ellipsometry. In this work, BATHT-SAM was employed as an interfacial layer on SiO2 to fabricate ultrathin film transistors (UTFTs, active layer thickness 16.09 nm). The device UTFT-I, made of 0.06 wt % S,S'-(9,10-bis(phenylethynyl)anthracene-2,6-diy1)bis(ethyne-2,1-diyObis(2hexylthiophene) (BATHT) solution on an n-octyltrichlorosilane-SAM/Si02 layer, showed no gate effect for the carrier transport behavior; however, the device UTFT-II, fabricated on BATHT-SAM/Si02, exhibited field effect mobilities of 0.04 cm2 Nr1 s (10,off 6.3 x 103 to 1.0 x 104). This can be attributed to the effect of BATHT-SAM inducing uniform coverage and ordering of BATHT molecules as an upper layer.