3-十四烷基噻吩 | 110851-66-6

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 中文名称: 3-十四烷基噻吩
• 中文别名: 3-十四基噻吩
• 英文名称: 3-tetradecylthiophene
• CAS: 110851-66-6
• 化学式: C₁₈H₃₂S
• 分子量: 280.518
• InChiKey: CAEIOINMYGTXNS-UHFFFAOYSA-N

物化性质

• 熔点：
  14.85°C (estimate)
• 沸点：
  348.22°C (estimate)
• 密度：
  0.9196 (estimate)
• 最大波长(λmax)：
  244nm(CHCl3)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  19
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  3-十四烷基噻吩 在 溴 作用下， 以 氯仿 为溶剂， 生成 2,5-二溴-3-十四烷基噻吩
  参考文献：
  名称：

  Regiocontrolled Synthesis of Poly(3-alkylthiophenes) Mediated by Rieke Zinc: Their Characterization and Solid-State Properties

  摘要：

  A systematically regiocontrolled synthesis of poly(3-alkylthiophenes) (P3AT) mediated by Rieke zinc is reported. Rieke zinc undergoes oxidative addition to 2,5-dibromo-3-alkylthiophene or 2-bromo-5-iodo-3-alkylthiophene regioselectively to afford 2-bromo-5-(bromozincio)-3-alkylthiophene (2) or 2-bromo-5-(iodozincio)-3-alkylthiophene (10). The intermediate 2 or 10 can be polymerized catalytically to a series of regiospecific poly(3-alkylthiophenes) using different catalysts. The regioregularity of the polymer chain is solely controlled by the structure of the catalyst. An almost completely regioregular head-to-tail (HT) P3AT (4) is obtained by using Ni(DPPE)Cl-2 ([1,2-bis-(diphenylphosphino)ethane]nickel(II) chloride). Use of Pd(DPPE)Cl-2 leads to a reduction in the regioregularity (70:30 HT/HH), while using Ni(PPh(3))(4) also leads to a much reduced regioregular P3AT (63:35 HT/HH). A totally regiorandom (50:50 HT/HH) P3AT (5) is afforded by using Pd(PPh(3))(4). The poly(3-butylthiophene) 4a is a 97% HT regioregular polymer. Other poly(3-alkylthiophenes) (alkyl = hexyl (4b), octyl (4c), decyl (4d), dodecyl (4e), and tetradecyl (4f)) are regioregular P3ATs with the HT linkage larger than 98.5% based on NMR analysis. Electronic absorption, X-ray diffraction, and crossed polarizing micrograph studies show that the cast films of the regioregular P3ATs (4) are self-organized, crystalline, flexible, and bronze-colored films with a metallic luster, while that of the regiorandom P3ATs (5) are amorphous and orange-colored films. The regioregular P3ATs exhibit a small bandgap (1.7 eV) which is 0.4 eV lower than that of regiorandom P3ATs (2.1 eV). Regioregular HT P3ATs have considerably improved electroconductivity and other physical properties over regiorandom P3ATs.

  DOI：

  10.1021/ja00106a027
• 作为产物：
  描述：

  3-[(E)-tetradec-1-enyl]thiophene 以86%的产率得到
  参考文献：
  名称：

  SHABANA, R.;AMER, ADEL;MARK, H. B. (JR);ZIMMER, HANS, PHOSPH., SULFUR AND SILICON AND RELAT. ELEM., 53,(1990) N-4, C. 299-306

  摘要：

  DOI：
• 作为试剂：
  描述：

  、 镁 、 、 溴代十四烷 、 3-溴噻吩 、 、 在 Ni(dppe)Cl2 氩 、 氮气 、 ice 、 盐酸 、 Brine 、 水 、 乙醚 、 magnesium sulfate 、 3-十四烷基噻吩 、 silica gel 、 正戊烷 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 17.0h， 生成 3-十四烷基噻吩
  参考文献：
  名称：

  NANOPARTICLES

  摘要：

  本发明涉及π-共轭聚合物的纳米颗粒。本发明还涉及包含这些聚合物纳米颗粒的水性组合物，制备纳米颗粒的工艺以及将这些纳米颗粒用于制造电子器件和元件的用途。

  公开号：

  US20160237205A1

文献信息

• Iron catalyzed cross coupling reactions of aromatic compounds
  申请人：——

  公开号：US20030220498A1

  公开（公告）日：2003-11-27

  A process for the production of compounds Ar—R 1 by means of a cross-coupling reaction of an organometallic reagent R 1 —M with an aromatic or heteroaromatic substrate Ar—X catalyzed by one or several iron salts or iron complexes as catalysts or pre-catalysts, present homogeneously or heterogeneously in the reaction mixture. This new invention exhibits substantial advantages over established cross coupling methodology using palladium- or nickel complexes as the catalysts. Most notable aspects are the fact that (i) expensive and/or toxic nobel metal catalysts are replaced by cheap, stable, commercially available and toxicologically benign iron salts or iron complexes as the catalysts or pre-catalysts, (ii) commercially attractive aryl chlorides as well as various aryl sulfonates can be used as starting materials, (iii) the reaction can be performed under “ligand-free” conditons, and (iv) the reaction times are usually very short.

  通过使用一种或多种铁盐或铁络合物作为催化剂或前催化剂，在有机金属试剂R1—M与芳香或杂芳底物Ar—X之间进行交叉偶联反应的方法，生产化合物Ar—R1。这一新发明相对于使用钯或镍络合物作为催化剂的传统交叉偶联方法具有显著优势。最值得注意的方面包括：(i) 昂贵和/或有毒的贵金属催化剂被廉价、稳定、商业可获得且毒理学上良性的铁盐或铁络合物替代作为催化剂或前催化剂，(ii) 商业上具吸引力的芳基氯化物以及各种芳基磺酸盐可用作起始材料，(iii) 反应可在“无配体”条件下进行，(iv) 反应时间通常非常短。
• Iron-Catalyzed Cross-Coupling Reactions
  作者：Alois Fürstner、Andreas Leitner、María Méndez、Helga Krause

  DOI：10.1021/ja027190t

  日期：2002.11.1

  and -CF(3) groups are compatible. The method also allows for consecutive cross-coupling processes in one pot, as exemplified by the efficient preparation of compound 12, and has been applied to the first synthesis of the cytotoxic marine natural product montipyridine 8. In contrast to the clean reaction of (hetero)aryl chlorides, the corresponding bromides and iodides are prone to a reduction of their

  简单的铁盐，如 FeCl(n)、Fe(acac)(n) (n = 2,3) 或 salen 络合物 4 被证明是高效、廉价、毒理学无害且环境友好的预催化剂，可用于许多交叉- 烷基或芳基格氏试剂、锌酸盐或有机锰物质与芳基和杂芳基氯化物、三氟甲磺酸盐甚至甲苯磺酸盐的偶联反应。原位制备的正式成分 [Fe(MgX)(2)] 的“无机格氏试剂”可能构成负责催化周转的传播物种，在许多情况下，即使在室温或室温以下，这种转化率也以前所未有的速度发生。由于反应条件异常温和，一系列官能团如酯、醚、腈、磺酸盐、磺酰胺、硫醚、缩醛、炔烃和 -CF(3) 基团是相容的。
• Synthesis and self-assembly of 5,5′-bis(phenylethynyl)-2,2′-bithiophene-based bolapolyphiles in triangular and square LC honeycombs
  作者：Hongfei Gao、Huifang Cheng、Zonghan Yang、Marko Prehm、Xiaohong Cheng、Carsten Tschierske

  DOI：10.1039/c4tc02347a

  日期：——

  A series of X-shaped 5,5′-bis(phenylethynyl)-2,2′-bithiophene-based bolaamphiphiles bearing two long lateral alkyl chains and two terminal glycerol groups has been synthesized by using Kumada and Sonogashira coupling reactions as key steps. The thermotropic liquid crystalline behavior of these compounds was investigated by POM, DSC and X-ray scattering. With elongation of the lateral alkyl chains two

  以熊田和Sonogashira偶联反应为关键步骤，合成了一系列带有两个X型5,5'-双（苯基乙炔基）-2,2'-联噻吩基的带有两个长侧链烷基和两个末端甘油基的Balaamphiphils。通过POM，DSC和X射线散射研究了这些化合物的热致液晶行为。与侧向烷基链两种不同液晶相的具有蜂窝结构，柱的伸长六角Δ/ p 6毫米，由（有缺陷的）形成三角形的蜂窝单元，和Col SQU / p 4毫米对于这些化合物，观察到带有方格的样品。UV和PL测量表明荧光特性使其成为潜在的候选荧光传感器设备。
• Dithiophene based X-shaped bolaamphiphiles: liquid crystals with single wall honeycombs and geometric frustration
  作者：Hongfei Gao、Yafei Ye、Leiyang Kong、Xiaohong Cheng、Marko Prehm、Helgard Ebert、Carsten Tschierske

  DOI：10.1039/c2sm26575c

  日期：——

  A series of 5,5′-diphenyl-2,2′-dithiophene based X-shaped polyphiles with two long lateral alkyl chains and terminal glycerol groups was synthesized and the liquid crystalline phases formed by these compounds were investigated by polarizing microscopy, DSC and XRD. These compounds form square (p4mm and p4gm) and hexagonal (p6mm) columnar LC phases. In these mesophases the molecules organize into polygonal honeycombs where the π-conjugated cores form the walls, fused at the edges by the hydrogen bonding networks between the glycerol units and filled by the lateral alkyl chains. By elongation of these chains, a series of polygonal honeycomb phases with a “single wall” structure, ranging from triangular via square and pentagonal to hexagonal was observed. Most triangular honeycombs appear to be defective and can be considered as mixtures of triangular cylinders with orientationally randomized rhombic cylinders. The transition from this improper triangular honeycomb to the square honeycomb takes place via a disordered isotropic phase. Addition of water to this isotropic phase gives rise to a true triangular honeycomb LC phase. Replacing one of the long lateral chains by a small methyl group leads to honeycombs formed by double walls instead of single walls. UV investigations indicate π-stacking of the aromatic cores organized in the honeycomb walls, which is of interest for the potential application of these materials in self assembled arrays of organic electronic material.

  合成了一系列基于5,5′-二苯基-2,2′-二硫代苯的X形聚合物，这些聚合物具有两个长侧链和端部甘油基团，并对这些化合物形成的液晶相进行了偏光显微镜、差示扫描量热法（DSC）和X射线衍射（XRD）研究。这些化合物形成了方形（p4mm和p4gm）和六角形（p6mm）柱状液晶相。在这些中间相中，分子组织成多边形蜂窝结构，π共轭核心形成墙壁，通过甘油单元之间的氢键网络在边缘连接，侧链则填充其中。通过延长这些链，观察到一系列具有“单墙”结构的多边形蜂窝相，形状从三角形到方形、五边形再到六角形。大多数三角形蜂窝似乎是缺陷结构，可以视为带有方向随机的菱形柱体的三角形柱体的混合体。这个不规则的三角形蜂窝到方形蜂窝的转变是通过一个无序的各向同性相进行的。向该各向同性相中添加水会产生一个真正的三角形蜂窝液晶相。用小的甲基取代其中一个长侧链会导致蜂窝形成双墙而不是单墙。紫外线研究表明，芳香核心在蜂窝墙中的堆叠现象，这对这些材料在自组装有机电子材料阵列中的潜在应用具有重要意义。
• Transition between triangular and square tiling patterns in liquid-crystalline honeycombs formed by tetrathiophene-based bolaamphiphiles
  作者：Xiaohong Cheng、Hongfei Gao、Xiaoping Tan、Xueyan Yang、Marko Prehm、Helgard Ebert、Carsten Tschierske

  DOI：10.1039/c3sc50664a

  日期：——

  self-assemble into a series of liquid-crystalline honeycombs, formed by the π-conjugated rods which enclose polygonal prismatic cells filled by the lateral chains. With increasing chain length a discontinuous transition from triangular to square honeycombs takes place. At this transition a periodic honeycomb composed of a mixture of square and triangular cells in a ratio 1 : 2 was formed at low temperature, whereas

  一系列5,5'''-二苯基四噻吩在两端各具有一个极性甘油基团和两个侧向柔性链，它们自组装成一系列液晶蜂窝，这些蜂窝由π共轭棒构成，这些棒包围了由多角形四方晶格填充的多角形晶格，侧链。随着链长的增加，发生了从三角形蜂窝到方形蜂窝的不连续过渡。在此过渡过程中，在低温下形成了由正方形和三角形单元以1：2的比例混合而成的周期性蜂窝，而在更高温度下，由三角形和随机分布的菱形单元组成的六方柱状相（一种新型的向列型向列型）由正方形蜂窝状碎片组成的均质相和等轴性各向同性相代表中间状态。