5-bromo-5'-dodecyl-2,2'-bithiophene | 188254-97-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 5-bromo-5'-dodecyl-2,2'-bithiophene
• 英文别名: 2-Bromo-5-(5-dodecylthiophen-2-yl)thiophene
• CAS: 188254-97-9
• 化学式: C₂₀H₂₉BrS₂
• 分子量: 413.486
• InChiKey: PVBJGBOZUJFAOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  5-bromo-5'-dodecyl-2,2'-bithiophene 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 三氯化铝 、 magnesium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Mesomorphic behaviors and charge carrier transport in terthiophene derivatives

  摘要：

  We synthesized dialkylterthiophene derivatives omega-substituted with cyclohexylethyl moiety, which exhibit smectic mesophases at room temperature, and investigated their charge carrier transport properties. In particular, transpentylcyclohexylethyl-propylterthiophene (3-TTP-C2CH-5) held SmB phase at room temperature. Furthermore, a 3:1 mixture of 3-TTP-C2CH-5 and (2-methylbutyl)-dodecylterthiophene (5*-TTP-12) showed the SmB phase between 101degreesC and -15degreesC, and the highly ordered smectic phase below -15degreesC. In the SmB phase of the mixture, hole and electron mobility was 10(-3) cm(2)/Vs, and independent of temperature and electric field over room temperature. However, below room temperature, the mobility depended on both temperature and electric field, as is often observed in organic amorphous solids and formarized by Gaussian disorder model, suggesting that the carrier transport in the smectic mesophase can be explained by the hopping conduction in disordered molecular sites.

  DOI：

  10.1080/15421400490434315
• 作为产物：
  描述：

  溴代十二烷 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 5-bromo-5'-dodecyl-2,2'-bithiophene
  参考文献：
  名称：

  Novel bifluorene based conjugated systems: synthesis and properties

  摘要：

  A series of novel bifluorene based systems was synthesised by a convergent approach by means of a Suzu'ki cross-coupling between 7,7'-bis-(4,4,5,5-tetramethyl-[1,3,2]dioxaboi-olan-2-yl)-9,9,9,9'-tetraoctyl-2,2'-bifluorene and suitable aryl-bromides. All the oligomers have been characterized by H-1, C-13 NMR, Fr-IR, UV-vis, PL spectroscopy and mass analyses. In particular, it has been demonstrated that the presence of strong electron donor (amines) or withdrawing (carboxylic esters) groups causes a bathochromic shift of the optical properties with respect to those of unsubstituted molecules. The effects of these functional groups on the HOMO-LUMO energy levels were investigated by cyclic voltammetry. Remarkably, the LUMO energy level of 7,7'-bis-[5-carbodecaoxy-2,2'-bithiophen-5-yl]-9,9,9',9'-tetraoctyl-2,2'-bifluorene (-3.07 eV) is strongly influenced by the presence of the ester functional group. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.010

文献信息

• Star­like substituted hexaarylbenzenes: synthesis and mesomorphic properties
  作者：Yanhou Geng、Andreas Fechtenkötter、Klaus Müllen

  DOI：10.1039/b101163o

  日期：——

  A series of hexaarylbenzenes (1–6) with a variety of different aryl arms (i.e. phenyl, biphenylyl, mono-, bi-, and terthienylyl) around a benzene core, decorated with flexible dodecyl chains on the terminal positions, were synthesized. Their mesomorphic behaviors were studied by differential scanning calorimetry (DSC), polarizing optical microscopy (POM) and X-ray diffraction (XD) techniques. Compounds 1–3, which have a hexaphenylbenzene core, form columnar mesophases. In particular 3, in which the core is composed of hexaphenylbenzene surrounded by thiophene rings, shows a stable columnar mesophase (d-Dh) over a large temperature range compared to its phenyl analogs, hexakis(4-dodecylphenyl-4-yl)benzene (1) and hexakis(4′-dodecylbiphenylyl)benzene (2). Compounds 4–6, hexa(oligo-α-thienylyl)benzenes, tend to form less ordered mesophases after annealing for a longer time. Compounds 4 and 5 form discotic nematic mesophases (Nd) at temperatures well below the decomposition temperature.

  合成了一系列六芳基苯 (1-6)，在苯核周围具有各种不同的芳基臂（即苯基、联苯基、单、双和三噻吩基），并在末端位置用柔性十二烷基链装饰。通过差示扫描量热法 (DSC)、偏光光学显微镜 (POM) 和 X 射线衍射 (XD) 技术研究了它们的介晶行为。化合物 1-3 具有六苯基苯核心，形成柱状中间相。特别是3，其核心由被噻吩环包围的六苯基苯组成，与其苯基类似物六(4-十二烷基苯基-4-基)苯相比，在很大的温度范围内表现出稳定的柱状中间相(d-Dh)。 1) 和六(4'-十二烷基联苯基)苯(2)。化合物 4-6，六（低聚-α-噻吩基）苯，在长时间退火后往往会形成有序性较低的中间相。化合物 4 和 5 在远低于分解温度的温度下形成盘状向列中间相 (Nd)。
• COMPOUND AND ORGANIC THIN FILM AND THIN FILM TRANSISTOR AND ELECTRONIC DEVICE
  申请人：Samsung Electronics Co., Ltd.

  公开号：US20200168806A1

  公开（公告）日：2020-05-28

  Disclosed are a compound represented by Chemical Formula 1A or 1B, an organic thin film including the same, a thin film transistor, and an electronic device. In Chemical Formula 1A or 1B, X 1 , X 2 , Ar 1 , R 1 to R 4 , and n 1 are the same as described in the detailed description.

  本发明涉及一种化合物，其化学式为1A或1B，以及包含该化合物的有机薄膜、薄膜晶体管和电子设备。在化学式1A或1B中，X1、X2、Ar1、R1至R4和n1的详细描述与上述相同。
• Compound and organic thin film and thin film transistor and electronic device
  申请人：Samsung Electronics Co., Ltd.

  公开号：US11038116B2

  公开（公告）日：2021-06-15

  Disclosed are a compound represented by Chemical Formula 1A or 1B, an organic thin film including the same, a thin film transistor, and an electronic device. In Chemical Formula 1A or 1B, X1, X2, Ar1, R1 to R4, and n1 are the same as described in the detailed description.

  本发明公开了化学式 1A 或 1B 所代表的化合物、包括该化合物的有机薄膜、薄膜晶体管和电子设备。 在化学式 1A 或 1B 中，X1、X2、Ar1、R1 至 R4 和 n1 与详细说明中所述的相同。
• Small asymmetric anthracene–thiophene compounds as organic thin-film transistors
  作者：Baji Shaik、Ji Hee Park、Tae Kyu An、Young Ri Noh、Soon Byung Yoon、Chan Eon Park、Young Jin Yoon、Yun-Hi Kim、Sang-Gyeong Lee

  DOI：10.1016/j.tet.2013.07.041

  日期：2013.9

  Anthracene and thiophene compounds are promising materials for OTFTs. We report here, the synthesis, as well as the physical, thermal, and optoelectronic properties of alkyl-substituted asymmetric anthracene-thiophene compounds connected by a bridged triple bond. The target molecules were synthesized using 2-bromoanthracene as the starting material, and the proceeding reactions included alkylation, bromination, and the Sonogashira coupling reaction. The synthesized compounds were both thermally and electrochemically stable. Among the synthesized compounds, HTEA (7a) and DTEA (7b) showed mobility and on/off ratio values of 1.3x10(-1) cm(2)/V s, 2.6 x 10(6) and 2.0x10(-2) cm(2)/V s, 1.0x10(6), respectively. (C) 2013 Elsevier Ltd. All rights reserved.
• Probe of Molecular Ordering in Photoconductive Smectic Mesophases by Transient Photocurrent Measurement
  作者：Masahiro Funahashi、Jun-Ichi Hanna

  DOI：10.1080/10587250108029959

  日期：2001.8