4-dodecyl-1-(trimethylsilylethynyl)benzene | 170698-87-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-dodecyl-1-(trimethylsilylethynyl)benzene
• 英文别名: ((4-dodecylphenyl)ethynyl)trimethylsilane；4-[(Trimethylsilyl)ethynyl]dodecylbenzene；4-dodecyl[(trimethylsilyl)ethynyl]benzene
• CAS: 170698-87-0
• 化学式: C₂₃H₃₈Si
• 分子量: 342.64
• InChiKey: UGEYXNLRXACCFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.38
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  4-dodecyl-1-(trimethylsilylethynyl)benzene 在 甲醇 、 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 potassium carbonate 、 二异丙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 4,8-bis-(4-dodecylphenylethynyl)-2,6-dimethylbenzo[1,2-d-4,5-d']bisoxazole diethylphosphonate ester
  参考文献：
  名称：

  通过炔烃取代来调节4,8-二取代的苯并二恶唑的光学和电子性质

  摘要：

  为了设计用于合成共轭材料的新的电子不足的结构单元，一系列新的反式合成了在4,8-位带有卤素或炔基取代基的苯并二恶唑。此外，还研究了这些修饰对光学和电子性能的影响。理论计算预测，各种炔烃的掺入可用于调节这些小分子的能级和带隙。使用两步反应序列，可以容易地以高收率制备目标4,8-二取代的苯并二恶唑：路易斯酸催化原酸酯环化，然后进行Sonogashira交叉偶联。实验确定的这些4,8-二取代的苯并二恶唑的HOMO值在-4.97至-6.20 eV的范围内，并且与理论预测值显示出合理的相关性，百分比偏差在2.4-12.8％的范围内。然而，当理论值外推至长链极限并与含有4,8-二取代的苯并双恶唑的共聚物进行比较时，实际HOMO值与预测HOMO值之间的偏差降低至小于3.5％。总的来说，这些结果表明这些4,8-二取代反式苯并二恶唑可用于合成具有可变和可预测电子特性的新型共轭材料。

  DOI：

  10.1021/jo201078w
• 作为产物：
  描述：

  溴苯 在 aluminum (III) chloride 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 hydrazine hydrate 、 三乙胺 、 三苯基膦 、 potassium hydroxide 作用下， 以 三乙二醇 为溶剂， 反应 34.0h， 生成 4-dodecyl-1-(trimethylsilylethynyl)benzene
  参考文献：
  名称：

  Pi-Extended Ethynyl 21,23-Dithiaporphyrins: A Synthesis and Comparative Study of Electrochemical, Optical, and Self-Assembling Properties

  摘要：

  21,23-Dithiaporphyrins were synthesized containing pi-extending ethynyl substituents at the meso positions. These porphyrins displayed highly bathochromic and broadened absorbance profiles spanning 400-900 nm with molar absorptivities ranging from 2500 to 300,000 M-1 cm(-1). Electrochemically, these ethynyl dithiaporphyrins undergo a single oxidation at 0.44 or 0.57 V and reduction at -1.17 or -1.08 V versus a ferrocene/ferrocenium internal standard depending on the type of functionalization appended to the ethynyl group. DFT calculations predict that the delocalization of the frontier molecular orbitals should expand onto the meso positions of the ethynyl 21,23-dithiaporphyrins; shrinking the HOMO-LUMO energy gap by destabilizing the HOMO energy. Indeed, the DFT results agree with our optical and electrochemical assessments. Finally, differential scanning calorimetry combined with cross-polarized optical microscopy and powder X-ray diffraction was used to assess the ability of these porph-yrins for long-range order. For the ethynylphenyl alkoxy 21,23-dithiaporphyin, birefringent, soft-crystalline-like domains were observed by polarized microscopy, which are marginally sustained by a low-level of crystallinity detected in the XRD, suggesting that long-range ordering is possible. Overall, ethynyl 21,23-dithiaporphyrins are able to harvest much lower energy light and possess lower oxidation and reduction potentials compared to their pyrrolic analogues, which are desirable properties for applications in organic electronics.

  DOI：

  10.1021/acs.joc.5b01299

文献信息

• Synthesis and Self-Assembly of Functionalized Hexa-peri-hexabenzocoronenes
  作者：Shunji Ito、Mike Wehmeier、J. Diedrich Brand、Christian Kübel、Rebekka Epsch、Jürgen P. Rabe、Klaus Müllen

  DOI：10.1002/1521-3765(20001201)6:23<4327::aid-chem4327>3.0.co;2-7

  日期：2000.12.1

  iron(III) chloride/nitromethane. Using this strategy three different substitution patterns were synthesized: 2-bromo-5,8,11.14,17-pentadodecylhexa-pecri-hexabenzocoronene (2a), 2,5-dibromo-8,11,14,17-pentadodecylhexa-peri-hexabenzocoronene (2b), and 2,11-dibromo5,8,14,17-pentadodecylhexa-peri-hexa-benzocoronene (2c). These bromo-substituted HBC derivatives were subjected to palladium catalyzed coupling

  先前已通过扫描隧道显微镜 (STM) 和扫描隧道光谱 (STS) 研究了六邻六苯并可罗烯 (HBC) 1b 的六烷基取代衍生物的单层。预计连接到芳香核的不同官能团（给电子或吸电子）将影响堆积模式，也可能影响电流-电压特性。为了提供合适的模型系统，开发了一种新的合成方法来合成功能化的 HBC 衍生物。这是通过适当溴取代的二苯基乙炔和 2,3,4,5-四芳基环戊二烯-2,4-二烯-1-酮的 [4 + 2]-环加成，然后用氯化铁 (III)/硝基甲烷氧化环脱氢来实现的. 使用该策略合成了三种不同的取代模式：2-bromo-5、8,11.14,17-pentadodecylhexa-pecri-hexabenzocoronene (2a), 2,5-dibromo-8,11,14,17-pentadodecylhexa-peri-hexabenzocoronene (2b), 和 2,11-dibromo5
• 一种光调控巨电热效应的混合液晶及其制备 方法
  申请人：西京学院

  公开号：CN108191711B

  公开（公告）日：2020-08-18

  一种光调控巨电热效应的混合液晶及其制备方法，在液晶混合物中增加具有良好伍配性的的偶氮苯液晶分子，所得混合液晶的具有大的介电各向异性，在电场作用下能够快速的取向，在撤销电场的条件下，又会恢复到初始的取向行为，并且在紫外光的照射下，能够发生顺反异构化，以及在电场强度对电热效应的作用下，获得相应性能的影响，能够节约能源，保护环境。
• A self assembled molecular zipper based on a perfluorophenyl-phenyl diacetylene motif
  作者：Lijin Shu、Zhongcheng Mu、Harald Fuchs、Lifeng Chi、Marcel Mayor

  DOI：10.1039/b517759f

  日期：——

  The synthesis and characterization of a molecular rod consisting of a pentafluorophenyl and a para-dodecylphenyl subunit linked by a diacetylene and its large area self assembly into perfect parallel lines consisting of interlocked molecular rods are reported and discussed.

  本文报告并讨论了由五氟苯基和十二烷基苯基亚基通过二乙炔连接而成的分子棒的综合和表征，以及其大面积自组装成由互锁分子棒组成的完美平行线的情况。
• A Curved Graphene Nanoribbon with Multi-Edge Structure and High Intrinsic Charge Carrier Mobility
  作者：Wenhui Niu、Ji Ma、Paniz Soltani、Wenhao Zheng、Fupin Liu、Alexey A. Popov、Jan J. Weigand、Hartmut Komber、Emanuele Poliani、Cinzia Casiraghi、Jörn Droste、Michael Ryan Hansen、Silvio Osella、David Beljonne、Mischa Bonn、Hai I. Wang、Xinliang Feng、Junzhi Liu、Yiyong Mai

  DOI：10.1021/jacs.0c07013

  日期：2020.10.28

  Structurally well-defined graphene nanoribbons (GNRs) have emerged as highly promising materials for the next-generation nanoelectronics. The electronic properties of GNRs critically depend on their edge topologies. Here, we demonstrate the efficient synthesis of a curved GNR (cGNR) with a combined cove, zigzag, and armchair edge structure, through bottom-up synthesis. The curvature of the cGNR is elucidated by the corresponding model compounds tetrabenzo[a,cd,j,lm]perylene (1) and diphenanthrene-fused tetrabenzo[a,cd,j,lm]perylene (2), the structures of which are unambiguously confirmed by the X-ray single-crystal analysis. The resultant multi-edged cGNR exhibits a well-resolved absorption at the near-infrared (NIR) region with a maximum peak at 850 nm, corresponding to a narrow optical energy gap of similar to 1.22 eV. Employing THz spectroscopy, we disclose a long scattering time of similar to 60 fs, corresponding to a record intrinsic charge carrier mobility of similar to 600 cm(2) V-1 s(-1) for photogenerated charge carriers in cGNR.
• Stabel, Andreas; Herwig, Peter; Muellen, Klaus, Angewandte Chemie, 1995, vol. 107, # 15, p. 1768 - 1770
  作者：Stabel, Andreas、Herwig, Peter、Muellen, Klaus、Rabe, Juergen P.

  DOI：——

  日期：——