2-溴-4-己基噻吩 | 210705-84-3

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 2-溴-4-己基噻吩
• 英文名称: 2-bromo-4-hexyl-thiophene
• 英文别名: 2-Bromo-4-hexylthiophene
• CAS: 210705-84-3
• 化学式: C₁₀H₁₅BrS
• 分子量: 247.199
• InChiKey: IKXKKFNSZQNRFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-溴-4-己基噻吩 在 magnesium 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以97%的产率得到3-己基噻吩
  参考文献：
  名称：

  A selective and direct synthesis of 2-bromo-4-alkylthiophenes: Convenient and straightforward approaches for the synthesis of head-to-tail (HT) and tail-to-tail (TT) dihexyl-2,2′-bithiophenes

  摘要：

  A straightforward method for the synthesis of 2-bromo-4-alkylthiophenes was developed, and the desired products were obtained in the highest chemical yields (>90%) reported to date. 2-Bromo-4-alkylthiophenes were synthesized by regioselective lithiating of 3-alkylthiophenes with n-BuLi and quenching with bromine at 78 degrees C. Moreover, a simple and efficient protocol for the synthesis of dihexyl-2,2'-bithiophenes was developed by employing 2-bromo-4-hexylthiophene instead of the commonly used monomer, 2-bromo-3-hexylthiophene. Kumada and Suzuki cross-coupling reactions were conducted to synthesize the desired products as head-to-tail (HT) and tail-to-tail (TT) regioisomers in high yields and excellent selectivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.100
• 作为产物：
  描述：

  3-己基噻吩 在 正丁基锂 、 四溴化碳 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以97.9%的产率得到2-溴-4-己基噻吩
  参考文献：
  名称：

  结构改性对吩噻嗪染料敏化太阳能电池性能的影响

  摘要：

  设计并合成了三种含吩噻嗪的新型染料DX1，DX2和DX3，用于染料敏化太阳能电池（DSSC）。三种染料的光物理，电化学和光伏性质已得到系统地研究。结果表明，具有0.5 mM鹅去氧胆酸（CDCA）的基于DX1的DSSC可获得5.69％的功率转换效率（PCE）。当将另一个缺电子的苯并噻二唑（BT）单元引入染料DX2和DX3的分子结构中时，吸收光谱将变宽。但是短路光电流密度（J sc由于电子传输受阻，器件的）降低，因此基于DX2的DSSC器件仅获得3.43％的PCE。此外，在DX3的吩噻嗪供体的氮原子上连接了具有高供电子能力的三苯胺（TPA）单元，从而提高了电子注入效率并减少了染料聚集。因此，改善了J sc，与基于DX2的染料相比，基于DX3的染料的PCE更高，为4.41％。

  DOI：

  10.1016/j.dyepig.2015.05.012

文献信息

• Alternating Copolymers Based on 2,1,3-Benzothiadiazole and Hexylthiophene: Positioning Effect of Hexyl Chains on the Photophysical and Electrochemical Properties
  作者：Ashraf A. El-Shehawy、Nabiha I. Abdo、Ahmed A. El-Barbary、Jae-Suk Lee

  DOI：10.1002/ejoc.201100182

  日期：2011.7.5

  A series of donor–acceptor alternating π-conjugated copolymers based on 2,1,3-benzothiadiazole and hexylthiophene units has been synthesized by the palladium-catalyzed Stille cross-coupling method. Various precursory monomers possessing dibromo and bis(tributylstannyl) functionalities were readily prepared in high yields. Microwave-assisted polymerization proved efficient for the production of high-molecular-weight

  通过钯催化的Stille交叉偶联方法合成了一系列基于2,1,3-苯并噻二唑和己基噻吩单元的供体-受体交替π共轭共聚物。具有二溴和双（三丁基甲锡烷基）官能团的各种前体单体很容易以高产率制备。事实证明，微波辅助聚合对于生产高分子量共聚物是有效的，范围从 13550 到 52490 g mol-1。所有共聚物在最常见的有机溶剂中都表现出优异的溶解性。通过热重分析和差示扫描量热法研究了这些共聚物的热性能，聚合物显示出高热稳定性。将苯并噻二唑单元并入聚己基噻吩链会影响光物理和电化学性能。所有聚合物的薄膜吸收光谱相对于溶液中相应的吸收带显着红移，并表现出更宽的吸收带。光学带隙估计在 2.02-1.74 eV 的范围内。最高占据和最低未占据分子轨道能级分别在 –5.37 至 –5.66 eV 和 –3.33 至 –3.44 eV 的范围内。在共聚物P3的沉积膜的X射线衍射分析中，在2θ=5.72°（15
• COMPOUNDS COMPRISING A LINEAR SERIES OF FIVE FUSED CARBON RINGS, AND PREPARATION THEREOF
  申请人：FALLIS Alexander Graham

  公开号：US20100004467A1

  公开（公告）日：2010-01-07

  The present application discloses methods for the production of organic compounds comprising a linear series of five fused carbon rings. Such compounds are useful in the production of electronic components, devices and materials. For example the methods disclosed permit the production of 2,9- and 2,10-disubstituted pentacene compounds and 2,6,9,13- and 2,6,10,13-tetrasubstituted compounds that present particularly advantageous properties for the manufacture of semiconductor materials, and may be used in devices such as for example thin film transistors and solar cells. These features are enhanced by π-π parallel stacking in the solid state. Also disclosed are compounds that are excellent candidates for use in the manufacture of semiconductor materials, and other components of electronic systems, by virtue of their solubility, crystal packing geometries, and electronic properties.

  本申请公开了生产含有一系列五个融合的碳环的有机化合物的方法。这类化合物在制造电子元件、设备和材料中非常有用。例如，所公开的方法允许生产2,9-和2,10-二取代的pentacene化合物以及2,6,9,13-和2,6,10,13-四取代化合物，这些化合物对于制造半导体材料具有特别有利的特性，并且可以用于例如薄膜晶体管和太阳能电池等设备中。这些特性在固态的π-π平行堆积中得到了增强。还公开了由于它们的溶解性、晶体堆积几何形状和电子性能，非常适合用于制造半导体材料和其他电子系统组件的化合物。
• Molecular Engineering of Carbazole Dyes for Efficient Dye-Sensitized Solar Cells
  作者：Jungeun Park、Eunji Lee、Jinho Kim、Youngjin Kang

  DOI：10.5012/bkcs.2013.34.5.1533

  日期：2013.5.20

  the range of 8-9% in the performance of dye sensitized solar cells (DSSCs). In particular, carbazole based dyes (MK dyes) and bis-fluorenylamine based dyes (JK dyes) have shown to have high efficiencies and long-term stability in DSSCs preformance. Koumura et al. has recently reported that the existence of long alkyl chains on the oligothiophene linkage of MK dye molecules can increase the electron lifetime

  有机敏化剂最近得到了改进，在染料敏化太阳能电池 (DSSC) 的性能方面达到了 8-9% 的高效率。特别是咔唑基染料（MK 染料）和双芴胺基染料（JK 染料）在 DSSC 的性能方面表现出高效率和长期稳定性。古村等人。最近报道，在 MK 染料分子的低聚噻吩键上存在长烷基链可以通过抑制染料的聚集和电子重组来增加电子寿命和开路电压。然而，对于 MK 染料，与其他高效有机染料相比，存在短路电流密度相对较低的问题。基于 MK 染料的 DSSC 的低短路电流密度（10-14 mAcm）源于咔唑的供体能力较弱，在长波长区域（650-750 nm）的光捕获能力较弱。而基于双芴胺的 JK 染料已显示在 DSSC 性能方面具有高短路电流密度 (> 14 mAcm)。与 MK 染料相比，这种高电流密度可能是由于胺的强供体能力和在长波长区域的吸收。因此，我们设想有机染料中低聚噻吩键与长烷基链和咔唑官能化胺供体的
• METHOD FOR MANUFACTURING CONJUGATED AROMATIC COMPOUND
  申请人：Oda Seiji

  公开号：US20110275859A1

  公开（公告）日：2011-11-10

  A method for manufacturing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (A) does not have (c1) a group represented by the following formula (10): wherein A 1 represents a C1-C20 alkoxy group etc.; (g1) a C1-C20 alkyl group which may be substituted with a fluorine atom etc.; and (h1) a C2-C20 acyl group which may be substituted with a fluorine atom etc., at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) wherein the aromatic compound (B) is structurally different from the above-mentioned aromatic compound (A), one or two leaving groups selected from the group consisting of an iodine atom, a bromine atom and a chlorine atom are bonded to an aromatic ring and the aromatic compound (B) does not have the above-mentioned (c1), (g1) and (h1) at the neighboring carbon atom to the carbon atom to which the leaving group is bonded, in the presence of (i) a nickel compound, (ii) a metal reducing agent, (iii) at least one ligand (L1) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-withdrawing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-withdrawing group and having no substituent at 2- and 9-positions, and (iv) at least one ligand (L2) selected from the group consisting of a 2,2′-bipyridine compound having at least one electron-releasing group and having no substituent at 3-, 6-, 3′- and 6′-positions, and a 1,10-phenanthroline compound having at least one electron-releasing group and having no substituent at 2- and 9-positions.

  一种制备共轭芳香化合物的方法，包括将含有一个或两个离去基团的芳香化合物（A）与含有相同结构的上述芳香化合物（A）或结构不同的芳香化合物（B）反应，其中这些离去基团选自碘原子、溴原子和氯原子，与芳香环结合，而芳香化合物（A）没有以下式（10）所代表的基团：其中A1代表C1-C20烷氧基等；（g1）代表C1-C20烷基基团，可能被氟原子等取代；以及（h1）代表C2-C20酰基基团，可能被氟原子等取代，与离去基团结合的碳原子的相邻碳原子处没有上述（c1）、（g1）和（h1），在（i）镍化合物、（ii）金属还原剂、（iii）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L1），具有至少一个吸电子基团且在3-、6-、3′-和6′-位置没有取代基，以及（iv）从2,2′-联吡啶化合物和1,10-邻菲啰啉化合物中选择的至少一种配体（L2），具有至少一个释电子基团且在3-、6-、3′-和6′-位置没有取代基团的情况下，在上述离去基团结合的碳原子的相邻碳原子处进行反应。
• [EN] POLYMERS AND COMPOUNDS BASED ON DIPYRROLO[1,2-B:1',2'-G][2,6]NAPHTHYRIDINE-5,11-DIONE<br/>[FR] POLYMÈRES ET COMPOSÉS À BASE DE DIPYRROLO[1,2-B:1',2'-G][2,6]NAPHTHYRIDINE-5,11-DIONE
  申请人：BASF SE

  公开号：WO2017068009A1

  公开（公告）日：2017-04-27

  The present invention relates to polymers comprising a repeating unit of the formula -[Ar-Y-Ar']- (v), and compounds of formula R10–Ar-Y-Ar'-R10' (I), wherein Y is a group of formula (A), and their use as organic semiconductor in organic devices, especially in organic photovoltaics and photodiodes, or in a device containing a diode and/or an organic field effect transistor. The polymers and compounds according to the invention can have excellent solubility in organic solvents and excellent film-forming properties. In addition, high efficiency of energy conversion, excellent field-effect mobility, good on/off current ratios and/or excellent stability can be observed, when the polymers and compounds according to the invention are used in organic field effect transistors, organic photovoltaics and photodiodes.

  本发明涉及包含重复单元的聚合物的公式为 -[Ar-Y-Ar']- (v)，以及公式为 R10–Ar-Y-Ar'-R10' (I) 的化合物，其中 Y 是公式 (A) 的一个基团，并且它们作为有机半导体在有机器件中的应用，特别是在有机光伏和光电二极管中，或在一个包含二极管和/或有机场效应晶体管的器件中。根据本发明的聚合物和化合物可以在有机溶剂中具有出色的溶解性和优秀的成膜性能。此外，当根据本发明的聚合物和化合物用于有机场效应晶体管、有机光伏和光电二极管时，可以观察到高能量转换效率、优异的场效应迁移率、良好的开关比和/或优异的稳定性。