2-溴-3-十六烷基噻吩 | 827343-08-8

• 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-3-十六烷基噻吩
• 英文名称: 2-bromo-3-hexadecylthiophene
• 英文别名: 2-bromo-3-n-hexadecylthiophene
• CAS: 827343-08-8
• 化学式: C₂₀H₃₅BrS
• 分子量: 387.468
• InChiKey: GOHORSZVGYZIGO-UHFFFAOYSA-N

物化性质

• 熔点：
  27 °C
• 沸点：
  428.1±25.0 °C(Predicted)
• 密度：
  1.079±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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-3-十六烷基噻吩 在 四氧化锇 、 三溴化硼 、 potassium carbonate 、 magnesium 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 、 乙腈 为溶剂， 反应 45.5h， 生成 3-(4-(3'-hexadecyl-[2,2'-bithiophen]-5-yl)phenoxy)propane-1,2-diol
  参考文献：
  名称：

  由四噻吩基的双亲两亲分子形成的液晶蜂窝体中三角形和正方形平铺图案之间的过渡†

  摘要：

  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。

  DOI：

  10.1039/c3sc50664a
• 作为产物：
  描述：

  1-hexadecylmagnesium bromide 在 N-溴代丁二酰亚胺(NBS) 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 作用下， 以 乙醚 、 氯仿 为溶剂， 生成 2-溴-3-十六烷基噻吩
  参考文献：
  名称：

  Self-assembly behaviour of conjugated terthiophenesurfactants in water

  摘要：

  水中共轭自组装体系引起了人们的极大兴趣，因为它们在生物相容超分子电子学中的潜在应用，但到目前为止，它们的超分子化学几乎没有被探索过。在这里，我们提出了两亲性三噻吩作为构建共轭聚集体的一种通用自组装平台，能够在不改变基本分子设计的情况下，提供不同形态的聚集体。我们详细探讨了这些两亲性三噻吩的设计参数，从而选择和合成了总共8种新的两亲性寡噻吩。通过吸光度和荧光光谱、动态光散射以及冷冻透射电子显微镜，我们研究了它们的聚集行为。发现临界微胞浓度低至0.01 mM，聚集体的尺寸范围从几纳米到200纳米不等。通过改变亲水和疏水基团的取代模式，聚集体的形态也可以调节，形成从球状和伸长的微胞到双层膜的不同类型的聚集体。值得注意的是，聚集对寡噻吩的电子和光谱特性几乎没有影响，这将对它们在超分子电子学中的应用引起关注。

  DOI：

  10.1039/c0nj00760a

文献信息

• Modulation of electronic properties of π-conjugated copolymers derived from naphtho[1,2-b:5,6-b′]dithiophene donor unit: A structure-property relationship study
  作者：Pranabesh Dutta、Hanok Park、Minjae Oh、Sushil Bagde、In Nam Kang、Soo-Hyoung Lee

  DOI：10.1002/pola.26691

  日期：2013.7.1

  set of three donor‐acceptor conjugated (D‐A) copolymers were designed and synthesized via Stille cross‐coupling reactions with the aim of modulating the optical and electronic properties of a newly emerged naphtho[1,2‐b:5,6‐b′]dithiophene donor unit for polymer solar cell (PSCs) applications. The PTNDTT‐BT, PTNDTT‐BTz, and PTNDTT‐DPP polymers incorporated naphtho[1,2‐b:5,6‐b′]dithiophene (NDT) as the

  通过Stille交叉偶联反应设计和合成了一组三种供体-受体共轭（D-A）共聚物，目的是调节新出现的萘并[1,2- b：5,6- b ']二噻吩供体单元，用于聚合物太阳能电池（PSC）应用。所述PTNDTT-BT，PTNDTT-BTZ，和PTNDTT-DPP聚合物并入萘并[1,2- b：5,6- b ']二噻吩（NDT）作为供体和2,2'-联噻唑（BTZ），苯并[ 1,2,5]噻二唑（BT）和吡咯并[3,4-c]吡咯-1,4（2H，5H）-二酮（DPP），作为受体单位。大量的实验技术，例如差示扫描量热法，热重分析法，紫外可见吸收光谱法，循环伏安法，X射线衍射和原子力显微镜用于确定共聚物的热，光学，电化学和形态学性质。通过引入不同吸电子强度的受体，这些共聚物的光学带隙可在1.58至1.9 eV之间有效调节，其HOMO和LUMO能级分别在-5.14至-5.26 eV和-3.13至-3.5 eV之
• 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。
• Self-assembly behaviour of conjugated terthiophenesurfactants in water
  作者：Patrick van Rijn、Dainius Janeliunas、Aurélie M. Brizard、Marc C. A. Stuart、Ger J. M. Koper、Rienk Eelkema、Jan H. van Esch

  DOI：10.1039/c0nj00760a

  日期：——

  Conjugated self-assembled systems in water are of great interest because of their potential application in biocompatible supramolecular electronics, but so far their supramolecular chemistry remains almost unexplored. Here we present amphiphilic terthiophenes as a general self-assembling platform for the construction of conjugated aggregates, providing access to aggregates with different morphologies without changing the basic molecular design. We explored the design parameters of these amphiphilic terthiophenes in detail, leading to the selection and synthesis of in total 8 new amphiphilic oligothiophenes. Their aggregation behaviour was investigated by absorbance and fluorescence spectroscopy, dynamic light scattering, and cryo-transmission electron microscopy. Critical micelle concentrations as low as 0.01 mM were found and different sized aggregates ranging from several nanometres up to 200 nm. The aggregate morphology could also be tuned by changing the substitution pattern of hydrophilic and hydrophobic moieties, leading to different types of aggregates ranging from globular- and elongated micelles to bilayers. Remarkably, aggregation had only little effect on the electronic and spectroscopic properties of the oligothiophenes, which will be of interest for their application in supramolecular electronics.

  水中共轭自组装体系引起了人们的极大兴趣，因为它们在生物相容超分子电子学中的潜在应用，但到目前为止，它们的超分子化学几乎没有被探索过。在这里，我们提出了两亲性三噻吩作为构建共轭聚集体的一种通用自组装平台，能够在不改变基本分子设计的情况下，提供不同形态的聚集体。我们详细探讨了这些两亲性三噻吩的设计参数，从而选择和合成了总共8种新的两亲性寡噻吩。通过吸光度和荧光光谱、动态光散射以及冷冻透射电子显微镜，我们研究了它们的聚集行为。发现临界微胞浓度低至0.01 mM，聚集体的尺寸范围从几纳米到200纳米不等。通过改变亲水和疏水基团的取代模式，聚集体的形态也可以调节，形成从球状和伸长的微胞到双层膜的不同类型的聚集体。值得注意的是，聚集对寡噻吩的电子和光谱特性几乎没有影响，这将对它们在超分子电子学中的应用引起关注。
• Benzo[1,2-b:4,5-b′]dithiophene-based copolymers applied in bottom-contact field-effect transistors
  作者：Mark A.M. Leenen、Fabio Cucinotta、Wojciech Pisula、Jürgen Steiger、Ralf Anselmann、Heiko Thiem、Luisa De Cola

  DOI：10.1016/j.polymer.2010.05.022

  日期：2010.6

  Three copolymers of benzo[1,2-b:4,5-b ']dithiophene and 3,3'-bis(alkyl)-5,5'-bithiophene (dodecyl, tetradecyl and hexadecyl side chains) have been synthesized through Stille copolymerization. The polymers have number-average molecular weights over 20 kg/mol, are well-packed in the bulk and thin film, and possess an ionization potential of -5.1 eV in thin film, which offers stability versus oxidation in environmental conditions. The thin film packing of the polymer with dodecyl side chains leads to an excimeric emission upon excitation, which is not observed for longer side chain lengths. The presence of the dimers responsible for this excimer formation results in a device performance improvement as well. Field-effect transistors fabricated from these copolymers have On/Off ratios >10(7), equal saturation and linear hole mobilities above 10(-2) cm(2)/Vs, almost no hysteresis and turn-on voltages around 0 V in bottom-contact devices. (C) 2010 Elsevier Ltd. All rights reserved.
• Effects of Olefin Content and Alkyl Chain Placement on Optoelectronic and Morphological Properties in Poly(thienylene vinylenes)
  作者：Joshua C. Speros、Henry Martinez、Bryan D. Paulsen、Scott P. White、Andrew D. Bonifas、Philip C. Goff、C. Daniel Frisbie、Marc A. Hillmyer

  DOI：10.1021/ma4009115

  日期：2013.7.9

  The effects of olefin content and alkyl chain placement on the properties of two poly(thienylene vinylene)-(PTV-) based polymer series were investigated. Polymers were prepared by ruthenium-catalyzed acyclic diene metathesis (ADMET) polymerization of four dipropenyl monomers. All polymers were thoroughly characterized with a variety of spectroscopic, thermal, and electronic techniques. Tuning the olefin content had direct impacts on optical and organic solar cell (OSC) behavior while systematic changes to alkyl substitution patterns manifested as differences in optical, thermal, and microstructural properties. Density functional theory (DFT) analysis provided support for the observed differences among all polymers. In addition, C-13 NMR and IR analysis of selected polymers helped to confirm the stereochemistry of the PTV backbone.