2,7-di(2-thienyl)-9,9-dihexylfluorene | 354580-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2,7-di(2-thienyl)-9,9-dihexylfluorene
• 英文别名: 2,7-bis(thiophen-2-yl)-9,9-bis-n-hexylfluorene；2,2′-(9,9-dihexyl-9H-fluorene-2,7-diyl)dithiophene；2,7-bis(thiophene-2-yl)-9,9-bis-(n-hexyl)fluorene；2,7-bis(2-thienyl)-9,9-dihexyl-9H-fluorene；2-[9,9-di(n-hexyl)-7-(2-thienyl)-9H-fluoren-2-yl]thiophene；2-[9,9-dihexyl-2-(thiophen-2-yl)-9H-fluoren-7-yl]thiophene；2,2'-(9,9-dihexyl-9H-fluorene-2,7-diyl)dithiophene；9,9-dihexyl-2,7-di(thiophen-2-yl)fluorene；2,2'-(9,9-Dihexyl-9H-fluorene-2,7-diyl)dithiophene；2-(9,9-dihexyl-7-thiophen-2-ylfluoren-2-yl)thiophene
• CAS: 354580-80-6
• 化学式: C₃₃H₃₈S₂
• 分子量: 498.797
• InChiKey: MMPZGOUETMIJAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  35
• 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：

  2,7-di(2-thienyl)-9,9-dihexylfluorene 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-[9,9-Dihexyl-7-(5-thiophen-2-ylthiophen-2-yl)fluoren-2-yl]-5-thiophen-2-ylthiophene
  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：

  9,9-二己基芴 在 四(三苯基膦)钯 、 溴 、 三氯化铁 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 3.0h， 生成 2,7-di(2-thienyl)-9,9-dihexylfluorene
  参考文献：
  名称：

  Synthesis and crystal structure and optical properties of fluorenic-core oligomers

  摘要：

  氟烯核寡聚物通过有机金属方法合成，显示出有趣的光致发光特性。对一个氟烯衍生物及三种同系寡聚物的晶体和分子结构进行了研究。二溴氟烯的螺旋衍生物显示出氢原子与溴原子之间非常强的相互作用。带有螺旋取代基的噻吩末端寡聚物采用特定的鱼骨排列，仅有末端噻吩残基重叠，且构象无序。全苯衍生物的晶体由靠面排列的离散分子堆积而成。带有线性烷基链的氟烯核心在9位上的分子，末端为噻吩环，表现出多晶型，其晶体结构为四方形，非常奇特，因为其松散的堆积允许相邻的噻吩环之间有良好的分离。 研究了这一系列的吸收和发射特性，并对单层器件的电致发光进行了表征。这些分子的光致发光特性强烈依赖于其结构组织，发射从无定相到晶体结构再到聚集形态表现出红移。 对这些寡聚物和寡噻吩烯的堆积进行比较，充分说明了所报道分子的光学特性。

  DOI：

  10.1039/b109089p

文献信息

• A Versatile Synthesis of Annulated Carbazole Analogs Involving a Domino Reaction of Bromomethylindoles with Arenes/Heteroarenes
  作者：Vasudevan Dhayalan、J. Arul Clement、Radhakrishnan Jagan、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.200801018

  日期：2009.2

  A ZnBr2-mediated arylation of aryl/heteroaryl methyl bromides with arenes at 80 °C led to the formation of arylated products, which underwent subsequent 1,5-sigmatropic rearrangement followed by electrocyclization and aromatization with loss of a diethylmalonate unit to afford the corresponding annulated products. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  ZnBr2 介导的芳基/杂芳基甲基溴与芳烃在 80°C 的芳基化形成芳基化产物，随后进行 1,5-σ 重排，然后进行电环化和芳构化，失去丙二酸二乙酯单元，得到相应的环化产物。产品。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• 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
• 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。
• Synthesis and properties of fluorene or carbazole-based and dicyanovinyl-capped n-type organic semiconductors
  作者：Ting Qi、Yunqi Liu、Wenfeng Qiu、Hengjun Zhang、Xike Gao、Ying Liu、Kun Lu、Chunyan Du、Gui Yu、Daoben Zhu

  DOI：10.1039/b715920j

  日期：——

  Dicyanovinyl-substituted compounds as electron transport materials are rarely studied, especially oligomers. A new series of fluorene or carbazole-based and dicyanovinyl-capped oligomers consisting of benzene or thiophene segments were synthesized using the Stille coupling reaction and their physical properties were investigated. Optical spectra show that the introduction of electron-accepting groups induces an intramolecular charge transfer, resulting in a shift of the absorption onset toward longer wavelengths. Moreover, the optical spectra of their films show intermolecular interactions, leading to bathochromic shifts with respect to the spectra in solution. Cyclic voltammetry indicates that they have suitable HOMO and LUMO energy levels, and the oligomers containing thiophene segments show lower LUMO levels. The X-ray crystallography of compound FTCN shows that the compound exhibits extended π stacking of the molecules. Thermal analysis reveals that they are thermally stable and no phase transition was observed at low temperatures.

  二氰乙烯基取代化合物作为电子传输材料的研究很少，尤其是寡聚物。通过Stille偶联反应合成了一系列苯环或噻吩片段的芴或咔唑基、二氰乙烯基封端的寡聚物，并研究了它们的物理性质。光学光谱显示，引入吸电子基团诱导了分子内电荷转移，导致吸收边向长波长方向移动。此外，它们薄膜的光学光谱显示了分子间相互作用，相对于溶液中的光谱，发生了红移。循环伏安法表明，它们具有合适的HOMO和LUMO能级，而含有噻吩片段的寡聚物显示出更低的LUMO能级。FTCN化合物的X射线晶体学显示，该化合物呈现出分子广泛的π堆积。热分析表明，它们具有良好的热稳定性，在低温下没有观察到相变。
• Lewis Acid Mediated One-Pot Synthesis of Aryl/Heteroaryl-Fused Carbazoles Involving a Cascade Friedel-Crafts Alkylation/Electrocyclization/Aromatization Reaction Sequence
  作者：Radhakrishnan Sureshbabu、Velu Saravanan、Vasudevan Dhayalan、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201001309

  日期：2011.2

  ]-fused carbazoles has been developed startingfrom suitably substituted 2/3-(bromomethyl)indoles and ar-enes under Lewis acid catalysis. The attractive feature ofthis protocol is the fact that a wide variety of π-conjugatedannulated carbazoles can be readily accessed by the appro-priate choice of arenes and heteroarenes. The annulationprotocol has been extended to (bromomethyl)benzene aswell as 2,

  在路易斯酸催化下，以适当取代的 2/3-（溴甲基）吲哚和芳烯为原料开发了]-稠合咔唑。本协议的有吸引力的特征是，可以通过竞争和杂种丁烯的应用选择可以容易地访问各种π缀合的咔唑。环化协议已扩展到（溴甲基）苯以及 2,5-双（溴甲基）噻吩。发现吲哚基-2-甲基乙酸酯的环化不如相应的2-(溴甲基)吲哚合适。然而，在苄体系的情况下，发现相应的醋酸盐更适用。在这项工作中开发的路易斯酸介导的级联环化序列可能会导致在多环芳香杂环领域的新应用。