2-溴-5-癸基噻吩 | 514188-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-溴-5-癸基噻吩
• 英文名称: 2-bromo-5-decylthiophene
• CAS: 514188-72-8
• 化学式: C₁₄H₂₃BrS
• 分子量: 303.307
• InChiKey: BLGUNQPKOOEOHU-UHFFFAOYSA-N

物化性质

• 沸点：
  135°C/0.56mmHg(lit.)
• 密度：
  1.166±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 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-5-癸基噻吩 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 magnesium 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 27.0h， 生成 5-bromo-2-(5-(5-(5-bromo-3-(5-decylthiophene-2-yl)thiophene-2-yl)thiophene-2-yl)thiophene-2-yl)-3-(5-decylthiophene-2-yl)thiophene
  参考文献：
  名称：

  Conformationally Twisted Semiconducting Polythiophene Derivatives with Alkylthiophene Side Chain: High Solubility and Air Stability

  摘要：

  We report the synthesis of polythiophene derivatives that contain decylthiophenyl side chains, using synthetic strategies that achieve high organic semiconductor Field effect mobilities by enhancing the pi-conjugation in the side-chain conjugated system. With increased charge densities, we obtained high field effect mobilities, LIP to 0.050 and 0.003 cm(2)/(V s) from poly(3,4"'-di(decylthiophenyl) sexithiophene) (PDTST) and poly(3,4"'-di(decylthiophenyl) quaterthiophene) (PDTQT), respectively. PDTQT and PDTST are characterized by UV-vis, DSC, A FM images, and G1XD patterns. Increased conformational rotation in the main backbone, caused by intramolecular repulsion between neighboring thiophene units, lowers the HOMO level and introduces remarkable chemical stability in the presence of air as well as increases processability due to high solubility. The high solubility and oxidative stability of PDTST and PDTQT indicate that these side-chain Conjugation system Strategies have the potential for improving other thiophene-based semiconducting polymers.

  DOI：

  10.1021/ma902396n
• 作为产物：
  描述：

  2-溴噻吩 在 magnesium 作用下， 以 四氢呋喃 为溶剂， 生成 2-溴-5-癸基噻吩
  参考文献：
  名称：

  Organic semiconductor material, organic semiconductor structure and organic semiconductor apparatus

  摘要：

  本发明旨在提供一种新型液晶有机半导体材料，该材料在形成薄膜的环境下非常稳定，并且可以很容易地形成薄膜，例如通过涂覆。液晶有机半导体材料由化学式1表示，其中R1和R2表示具有7到20个碳原子的相同烷基基团。还提供了一种液晶有机半导体材料，其特征在于由化学式2表示，其中R3和R4表示具有7到20个碳原子的相同烷基基团。

  公开号：

  US07935828B2

文献信息

• [EN] HETEROACENES FOR ORGANIC ELECTRONICS<br/>[FR] HÉTÉROACÈNES POUR L'ÉLECTRONIQUE ORGANIQUE
  申请人：BASF SE

  公开号：WO2015128779A1

  公开（公告）日：2015-09-03

  The present invention provides compounds of formula 1 wherein X1 and X2 are independently from each other O, S or Se, and an electronic device comprising the compounds as semiconducting material.

  本发明提供了式1的化合物，其中X1和X2分别独立地为O、S或Se，以及包含该化合物作为半导体材料的电子设备。
• End-Capping Groups for Small-Molecule Organic Semiconducting Materials: Synthetic Investigation and Photovoltaic Applications through Direct C-H (Hetero)arylation
  作者：Te-Jui Lu、Po-Han Lin、Kun-Mu Lee、Ching-Yuan Liu

  DOI：10.1002/ejoc.201601257

  日期：2017.1.3

  A Pd-catalyzed C–H (hetero)arylation methodology has been optimized for the efficient synthesis of various useful end-capping groups that are widely applied in small-molecule optoelectronic materials. We report herein the synthesis of a broad scope of target molecules ranging from donor-type through acceptor-type to hybrid-type end-capping groups. To demonstrate their application in dye-sensitized

  Pd催化的C-H（杂）芳基化方法已被优化用于有效合成广泛应用于小分子光电材料的各种有用的封端基团。我们在此报告了范围广泛的目标分子的合成，范围从供体型到受体型到混合型封端基团。为了证明它们在染料敏化太阳能电池中的应用，我们设计了两种新的 D-A-π-A' 型有机敏化剂（CYL-3 和 CYL-4），它们是通过连续 C -H 芳基化使用容易获得的封端基团。基于 CYL-3 和 CYL-4 的器件的 Voc 值为 0.67–0.71 V，Jsc 值为 10.07–11.63 mA cm–2，FF 值为 70.6–72.9 %，对应的总功率转换效率为 4.76– 6.02%。
• Synthesis and thermal behaviour of α,α′-didecyloligothiophenes
  作者：Sergei Ponomarenko、Stephan Kirchmeyer

  DOI：10.1039/b209176c

  日期：2003.2.5

  α,α′-Didecylquater-, -quinque- and -sexi-thiophenes were synthesized by Kumada cross-coupling and oxidative coupling reactions. For the former reaction Pd(dppf)Cl2 was found to be a more efficient catalyst than the usually applied Ni(dppp)Cl2. Thermal behaviour of all new oligothiophenes was investigated by differential scanning calorimetry and polarizing optical microscopy. It was shown that all these compounds possess not only crystal phases but also high temperature ordered smectic mesophases and that the clearing point increases linearly with the number of conjugated thiophene rings. A degree of order in the crystal phase was estimated on the basis of thermodynamic data. The highest degree of order was proposed for α,α′-didecylquaterthiophene, which explains why the mobility of end-α,α′-capped quaterthiophenes in FET (field effect transistor) devices is comparable or sometimes better than those of corresponding quinque- and sexi-thiophene derivatives.

  通过 Kumada 交叉偶联和氧化偶联反应合成了δ,δ,δ²-二癸基季铵盐、奎宁盐和六噻吩。在前一种反应中，发现钯（dppf）Cl2 是比通常使用的镍（dppp）Cl2 更有效的催化剂。通过差示扫描量热法和偏振光学显微镜研究了所有新型低聚噻吩的热性能。结果表明，所有这些化合物不仅具有晶体相，而且还具有高温有序共晶介相，其清澈点随共轭噻吩环数量的增加而线性增加。根据热力学数据估算了晶体相的有序度。δ,δâ²-二癸基四联噻吩的有序度最高，这也解释了为什么在 FET（场效应晶体管）器件中，末端δ,δâ²-封端的四联噻吩的迁移率与相应的五联噻吩和六联噻吩衍生物相当，有时甚至更好。
• Large Area Liquid Crystal Monodomain Field-Effect Transistors
  作者：Albert J. J. M. van Breemen、Peter T. Herwig、Ceciel H. T. Chlon、Jörgen Sweelssen、Herman F. M. Schoo、Sepas Setayesh、Willie M. Hardeman、Christian A. Martin、Dago M. de Leeuw、Josué J. P. Valeton、Cees W. M. Bastiaansen、Dirk J. Broer、Andreea R. Popa-Merticaru、Stefan C. J. Meskers

  DOI：10.1021/ja055337l

  日期：2006.2.1

  Butyl, hexyl, and decyl derivatives of the liquid-crystal line organic semiconductor 5,5 double prime -bis(5alkyl-2-thienylethynyl)-2,2':5',2double prime -terthiophene were synthesized and studied with respect to their structural, optical, and electrical properties. By means of an optimized thermal annealing scheme the hexyl and decyl compounds could be processed into self-assembled monodomain films of up to 150 mm in diameter. These were investigated with X-ray diffractometry, which revealed a clearly single-crystalline monoclinic morphology with lamellae parallel to the substrate. Within the lamellae the molecules were found to arrange with a tilt of about 50 degrees with the rubbing direction of the polyimide alignment layer. The resulting, close side-to-side packing was confirmed by measurements of the UV/vis absorption, which showed a dichroic ratio of 19 and indicated H-aggregation. AFM analyses revealed self-affinity in the surface roughness of the monodomain. The compounds showed bipolar charge transport in TOF measurements, with hole mobilities reaching up to 0.02 cm(2)/Vs and maximum electron mobilities around 0.002 cm(2)/Vs. The hexyl derivative was processed into large-area monodomain top-gate field-effect transistors, which were stable for months and showed anisotropic hole mobilities of up to 0.02 cm(2)/Vs. Compared to multidomain bottom-gate transistors the monodomain formation allowed for a mobility increase by 1 order of magnitude.
• 2,8- and 2,9-Diboryltetracenes as Useful Building Blocks for Extended π-Conjugated Tetracenes
  作者：Takakazu Kimoto、Kenro Tanaka、Yoshimasa Sakai、Akira Ohno、Kenji Yoza、Kenji Kobayashi

  DOI：10.1021/ol901420p

  日期：2009.8.20

  Ir-catalyzed direct diborylation of tetracene gave a 1:1 mixture of 2,8- and 2,9-bis[(pinacolato)boryl]tetracenes, which were separated by recrystallization. These diboryltetracenes are useful building blocks for the regiospecific synthesis of extended pi-conjugated tetracenes directed to semiconductors for organic field-effect transistors (OFETs). Syntheses of thiophene-tetracene-thiophene, thiophene-tetracene-bithiophene-tetracene-thiophene, and thiophene-tetracene-anthracene-tetracene-thiophene pi-systems have been achieved on the basis of the 2,8- and 2,9-diboryltetracenes.