3-(10-bromodecyl)thiophene | 125878-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(10-bromodecyl)thiophene
• CAS: 125878-93-5
• 化学式: C₁₄H₂₃BrS
• 分子量: 303.307
• InChiKey: VXRIWDAIEVVNHU-UHFFFAOYSA-N

物化性质

• 沸点：
  120 °C(Press: 0.001 Torr)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  16
• 可旋转键数：
  10
• 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：

  3-(10-bromodecyl)thiophene 在 N-溴代丁二酰亚胺(NBS) 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 3-(10-bromodecyl)-2,2'-bithiophene
  参考文献：
  名称：

  Synthesis and characterization of oligo- and crown ether-substituted polythiophenes-a comparative study

  摘要：

  描述了通过分离氧烷烃链（2, 7-11）或直接 π-共轭（4, 12-15）合成两系列带有冠醚和寡聚醚基团的噻吩化合物。电氧化聚合导致相应的冠醚和寡聚醚功能化聚噻吩 P2、P7-P11，以及 P4、P12。它们的电化学和光谱特性依赖于间隔链的长度和醚单位的类型。聚合物显示出较高的平均共轭性。发现碱金属离子对多种聚合物的电化学行为具有显著且强烈的影响。选择性与无溶剂壳的阳离子大小与冠醚单元的内径相匹配。光电化学实验证实，红氧性质的变化是由于聚合物氧化时，反离子向薄膜内扩散受限所致。由于结构变化，获得了对不同阳离子敏感的新型材料。重要的是，在这些共轭聚合物中，与碱金属阳离子和醚单元的选择性宿主-客体相互作用相对应的化学信息被转化为电信号的变化。

  DOI：

  10.1039/a902823d
• 作为产物：
  描述：

  3-[8-(4-methoxyphenoxy)octyl]thiophene 在 n-hexadecyltrimethylphosphonium bromide 、 氢溴酸 、 乙酸酐 作用下， 以70%的产率得到3-(10-bromodecyl)thiophene
  参考文献：
  名称：

  Baeuerle, Peter; Wuerthner, Frank; Heid, Stephan, Angewandte Chemie, 1990, vol. 102, # 4, p. 414 - 415

  摘要：

  DOI：

文献信息

• Synthesis of 4-[ω-(3-Thienyl)alkyl]pyridines and 4-[ω-(3-Thienyl)alkyl]-2,2'-bipyridines
  作者：JX Wang、M Pappalardo、FR Keene

  DOI：10.1071/ch9951425

  日期：——

  The synthesis is reported of 4-[ω-(3-thienyl)alkyl]pyridine (2), 4-[ω-(3-thienyl)alkyl]-2,2′- bipyridine (3) and 4-methyl-4'-[ω-(3-thienyl)alkyl]-2,2′-bipyridine (4), where the length of the alkyl chain is varied (n = 2, 5, 7, 9, 11). The synthetic methodology involved the reaction of the 3-(ω- bromoalkyl ) thiophen with the anions derived from 4-methylpyridine, 4-methyl-2,2′-bipyridine or 4,4′-dimethyl-2,2′-bipyridine by lithiation . The n.m.r. (1H and 13C) and electronic spectral characteristics of the compounds are discussed.

  报告了 4-[ω-(3-噻吩基)烷基]吡啶 (2)、4-[ω-(3-噻吩基)烷基]-2,2′-联吡啶 (3) 和 4-甲基-4'-[ω-(3-噻吩基)烷基]-2,2′-联吡啶 (4) 的合成，其中烷基链的长度是变化的（n = 2、5、7、9、11）。合成方法是将 3-(ω-溴烷基)噻吩与来自 4-甲基吡啶、4-甲基-2,2′-联吡啶或 4,4′-二甲基-2,2′-联吡啶的阴离子通过石化作用进行反应。讨论了这些化合物的 n.m.r.（1H 和 13C）和电子光谱特性。
• Synthesis of Novel Alkyl- and Aryl Sulfides and Thiols as Precursors for Self-Assembled Monolayers on Gold
  作者：Livain Breau、Mohamed Touaibia、Marc-André Desjardins、Alexandre Provençal、Daniel Audet、Christelle Médard、Mario Morin

  DOI：10.1055/s-2004-831163

  日期：——

  A series of 4-alkyl-1-bromosulfanylbenzenes having S-methyl 2, S-t-butyl 3, S-trityl 4, S-benzyl 5, and S-silylethoxymethyl 6 substituents were prepared and evaluated for their ability to form a monolayer consisting of an S-aryl adsorbate on Au (111) surface. The monolayer was formed via the selective hydrolytic removal of an alkyl group protecting the sulfur functionality upon adsorbtion onto the gold surface. Thiols having variable carbon chain length and a peripheral thiophene moiety 9, 10, 17, 18 and 23-26 were also prepared.

  制备了一系列4-烷基-1-溴硫代苯，包括S-甲基2、S-叔丁基3、S-三苯甲基4、S-苄基5和S-硅乙氧甲基6取代基，并评估它们在金(111)表面形成由S-芳基吸附物组成的单层膜的能力。单层膜的形成是通过在吸附到金表面时选择性地水解去除保护硫官能团的烷基。还制备了具有可变碳链长度和外围噻吩基团的硫醇9, 10, 17, 18和23-26。
• Intertwined Lamello-Columnar Coassemblies in Liquid-Crystalline Side-Chain Π-Conjugated Polymers: Toward a New Class of Nanostructured Supramolecular Organic Semiconductors
  作者：Danli Zeng、Ibtissam Tahar-Djebbar、Yiming Xiao、Farid Kameche、Navaphun Kayunkid、Martin Brinkmann、Daniel Guillon、Benoît Heinrich、Bertrand Donnio、Dimitri A. Ivanov、Emmanuelle Lacaze、David Kreher、Fabrice Mathevet、André-Jean Attias

  DOI：10.1021/ma4020356

  日期：2014.3.11

  A set of liquid-crystalline polymeric systems, associating at once the regioregular polythiophene backbone and pending mesogenic triphenylenes, is reported. Two series, namely regular homopolymers and alternating copolymers, were prepared by adapting a Grignard metathesis-based methodology, allowing some of the relevant structural parameters to be sequentially and independently modified. The thermal and self-organization behaviors of these uncommon macromolecular systems were investigated by polarized-light optical microscopy, differential scanning calorimetry and temperature-dependent small-angle X-ray scattering. Most polymers self-organize into mesophases possessing intertwined lamello-columnar morphologies, resulting from the simultaneous coexistence of lamellar and columnar sublattices. The successful preparation of oriented thin films of several of these polymeric homologues allowed further investigations by atomic force microscopy, transmission electron microscopy, electron diffraction, and grazing-incidence SAXS, which provided a deeper insight of the intricate supramolecular organizational modes, including the complete elucidation of the structure of the lamello-columnar mesophases. This simple and versatile strategy provides a route to elaborate polymeric materials incorporating two intercalated separate pathways toward charge carrier transport, of paramount importance for future electronic and optoelectronic applications.
• Self-Organized Hole Transport Layers Based on Polythiophene Diblock Copolymers for Inverted Organic Solar Cells with High Efficiency
  作者：Kai Yao、Lie Chen、Xun Chen、Yiwang Chen

  DOI：10.1021/cm400297p

  日期：2013.3.26

  Novel fluoroalkyl side-chain diblock copolymers, poly(3-hexylthiophene)-block-poly[3-(4-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyloxy)phenyl)-decyloxy)thiophene] (P3HT-b-P3FAT), were successfully synthesized by Grignard metathesis (GRIM) polymerization. Driven by the low surface energy of fluoroalkyl side chains, the fluorinated polymers can spontaneously segregate on the surface of poly-(3-hexylthiophene) (P3HT) during spin-coating processes. As the P3HT block increases in the copolymer, higher concentrations of fluoropolymers are required to form the self-assembled monolayer on the surface. The fluorinated part forms an interfacial dipole that shifts the work function of the anode metal, while the P3HT block can interact with the P3HT donor for hole transport. With this self-assembly hole transport layer to align the energy levels, P3HT:PCBM photovoltaic devices are easily fabricated to achieve improved performance. Overall, devices prepared with 1.5 mg mL(-1) copolymer PFT-3HT with a 3:1 ratio of P3HT to P3FAT block in the active layer solution displayed PCE values of up to 4.6% (50% PCE increase over a PEDOT:PSS control device) and showed a significant long-term stability in excess of 300 h in air.
• BAUERLE, PETER;WURTHNER, FRANK;HEID, STEPHAN, ANGEW. CHEM., 102,(1990) N, C. 414-415
  作者：BAUERLE, PETER、WURTHNER, FRANK、HEID, STEPHAN

  DOI：——

  日期：——