2-bromo-5-[7-(5-bromo-2-thienyl)-9,9-dihexyl-9H-fluoren-2-yl]thiophene | 928853-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-bromo-5-[7-(5-bromo-2-thienyl)-9,9-dihexyl-9H-fluoren-2-yl]thiophene
• 英文别名: 5,5'-(9,9-dihexyl-9H-fluorene-2,7-diyl)bis(2-bromothiophene)；2,7-bis(5-bromothiophen-2-yl)-9,9-di-n-hexylfluorene；2-Bromo-5-[7-(5-bromothiophen-2-yl)-9,9-dihexylfluoren-2-yl]thiophene；2-bromo-5-[7-(5-bromothiophen-2-yl)-9,9-dihexylfluoren-2-yl]thiophene
• CAS: 928853-19-4
• 化学式: C₃₃H₃₆Br₂S₂
• 分子量: 656.589
• InChiKey: LXVSFRVXWYOGTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.6
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-5-[7-(5-bromo-2-thienyl)-9,9-dihexyl-9H-fluoren-2-yl]thiophene 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 2-Bromo-5-[5-[7-[5-(5-bromothiophen-2-yl)thiophen-2-yl]-9,9-dihexylfluoren-2-yl]thiophen-2-yl]thiophene
  参考文献：
  名称：

  Synthesis and characterization of novel N-carbazole end-capped oligothiophene-fluorenes

  摘要：

  A series of novel N-carbazole end-capped oligothiophene-fluorenes was synthesized using Ullmann coupling, bromination, and Suzuki coupling reactions. The optical, thermal, and electrochemical properties of these materials can be tuned by varying the conjugation length of the oligothiophene segment. The terminal carbazole and central fluorene moieties of the resulting materials are beneficial for their morphology, conjugation length, and solubility. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.073
• 作为产物：
  描述：

  9,9-二己基-2,7-二溴代芴 在 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-bromo-5-[7-(5-bromo-2-thienyl)-9,9-dihexyl-9H-fluoren-2-yl]thiophene
  参考文献：
  名称：

  Using bis(pinacolato)diboron to improve the quality of regioregular conjugated co-polymers

  摘要：

  我们展示了通过Suzuki同聚合反应，利用双(频哪醇基)二硼直接聚合对称、双溴、噻吩基单体，以较少步骤形成共聚物的方法。通过采用两种方法（新方法和常用的Stille共聚法）制备四种噻吩基共聚物，并将这种方法与Stille共聚法进行对比。通过MALDI-TOF质谱分析，我们证明这种方法能生成高质量、均一的聚合物，其端基分布狭窄。通过改变单体的电负性，我们初步实现了对这些端基的控制，按照电负性增加的顺序，分别形成双氢端基、单氢单溴端基或双溴端基的聚合物。

  DOI：

  10.1039/c0jm02359k

文献信息

• Synthesis and application of H-Bonded cross-linking polymers containing a conjugated pyridyl H-Acceptor side-chain polymer and various carbazole-based H-Donor dyes bearing symmetrical cyanoacrylic acids for organic solar cells
  作者：Duryodhan Sahu、Harihara Padhy、Dhananjaya Patra、Dhananjay Kekuda、Chih-Wei Chu、I.-Hung Chiang、Hong-Cheu Lin

  DOI：10.1016/j.polymer.2010.10.018

  日期：2010.12

  various proton-donor (H-donor) solar cell dyes containing 3,6- and 2,7-functionalized electron-donating carbazole cores bearing symmetrical thiophene linkers and cyanoacrylic acid termini with a proton-acceptor (H-acceptor) side-chain homopolymer carrying pyridyl pendants (with 1/2 M ratio of H-donor/H-acceptor). The supramolecular H-bonded structures between H-donor dyes and the H-acceptor side-chain

  通过络合包含3,6-和2,7-官能化给电子咔唑核的对称的各种质子-供体（H-供体）太阳能电池染料，生成了一系列新型的氢键（H键）交联聚合物。噻吩接头和氰基丙烯酸末端带有带有吡啶基侧基的质子受体（H受体）侧链均聚物（H受体/ H受体的比率为1/2 M）。通过FTIR测量证实了H-供体染料与H-受体侧链聚合物之间的超分子H键结构。研究了超分子体系结构对光学，电化学和有机光伏（OPV）性能的影响。根据DFT（密度泛函理论）计算，D1-D4染料。在100 mW / cm 2的AM 1.5白光照射下，体异质结（BHJ）OPV电池器件包含作为电子供体的H键键合聚合物（PDFTP / D1-D4）的活性层，并与[6,6]-混合。探索了以1：1的重量比作为电子受体的苯基C 61-丁酸甲酯（PCBM）。通过初步研究，包含重量比为1：1的H键键聚合物PDFTP / D2和PCBM的OPV器件显示出0.31％的
• Synthesis and properties of N-carbazole end-capped conjugated molecules
  作者：Vinich Promarak、Somsak Ruchirawat

  DOI：10.1016/j.tet.2006.12.011

  日期：2007.2

  A series of novel N-carbazole end-capped pi-conjugated molecules were synthesized by a divergent approach with the use of bromination, Suzuki cross-coupling, and Ullmann reactions and their physical properties were investigated. In dilute solution, UV-vis absorption spectra displayed bathochromic shift with respect to their conjugated backbones, and photoluminescence spectra showed emission maxima in the blue region. Thermal analysis revealed that they are thermally stable semi-crystalline and amorphous materials. All molecules exhibited good electrochemical stability with high-lying HOMO energy levels and have potential applications as hole-transporting and light-emitting layers in organic light-emitting diodes or as host materials for electrophosphorescent applications. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and characterization of novel N-carbazole end-capped oligothiophene-fluorenes
  作者：Vinich Promarak、Auradee Pankvuang、Somsak Ruchirawat

  DOI：10.1016/j.tetlet.2006.12.073

  日期：2007.2

  A series of novel N-carbazole end-capped oligothiophene-fluorenes was synthesized using Ullmann coupling, bromination, and Suzuki coupling reactions. The optical, thermal, and electrochemical properties of these materials can be tuned by varying the conjugation length of the oligothiophene segment. The terminal carbazole and central fluorene moieties of the resulting materials are beneficial for their morphology, conjugation length, and solubility. (c) 2006 Elsevier Ltd. All rights reserved.
• Using bis(pinacolato)diboron to improve the quality of regioregular conjugated co-polymers
  作者：Frank Brouwer、Jan Alma、Hennie Valkenier、Thomas P. Voortman、Jorrit Hillebrand、Ryan C. Chiechi、Jan C. Hummelen

  DOI：10.1039/c0jm02359k

  日期：——

  We demonstrate the use of bis(pinacolato)diboron to directly polymerize symmetric, bisbromo, thiophene-based monomers via a Suzuki homo-polymerization to form co-polymers in less steps than the corresponding co-polymerization. We compare this method to the commonly used Stille co-polymerization by preparing four thiophene-based co-polymers using both methods. We use MALDI-TOF mass spectrometry to show that this new method produces high-quality, uniform polymers with narrow distributions of end-groups. By varying the electronegativity of the monomers, we demonstrate rudimentary control over these end-groups, forming either bis-H-, mono-H-mono-Br-, or bis-Br-terminated polymers in order of increasing electronegativity.

  我们展示了通过Suzuki同聚合反应，利用双(频哪醇基)二硼直接聚合对称、双溴、噻吩基单体，以较少步骤形成共聚物的方法。通过采用两种方法（新方法和常用的Stille共聚法）制备四种噻吩基共聚物，并将这种方法与Stille共聚法进行对比。通过MALDI-TOF质谱分析，我们证明这种方法能生成高质量、均一的聚合物，其端基分布狭窄。通过改变单体的电负性，我们初步实现了对这些端基的控制，按照电负性增加的顺序，分别形成双氢端基、单氢单溴端基或双溴端基的聚合物。