4-十二烷基-2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)噻吩 | 1173788-58-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 4-十二烷基-2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)噻吩
• 中文别名: 4-十二烷基-2-(4,4,5,5-四甲基-1,3,2-二氧硼烷-2-基)噻吩
• 英文名称: 2-(4-dodecylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 2-(4-Dodecylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1173788-58-3
• 化学式: C₂₂H₃₉BO₂S
• 分子量: 378.427
• InChiKey: KFTOUTPAXZWQLP-UHFFFAOYSA-N

物化性质

• 沸点：
  467.6±33.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  26
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-十二烷基-2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)噻吩 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 palladium diacetate 、 potassium carbonate 、 三甲基乙酸 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 、 甲苯 为溶剂， 反应 33.0h， 生成 5',5''-(benzo[c][1,2,5]selenadiazole-4,7-diyl)bis(3'-dodecyl-2,2'-bithiophene-5-carbonitrile)
  参考文献：
  名称：

  Synthesis and characterization of acceptor–donor–acceptor-based low band gap small molecules containing benzoselenadiazole

  摘要：

  接受者-给体-接受者型化合物5′,5″-(苯并[c][1,2,5]硒唑二唑-4,7-二基)双(3′-十二烷基-2,2′-联噻吩-5-碳腈) (9) 和 4,4′-(5,5′-(苯并[c][1,2,5]硒唑二唑-4,7-二基)双(3-十二烷基噻吩-5,2-二基))二苯腈 (10) 被设计并合成。这些化合物在末端位置上有所不同，化合物9带有噻吩含氰基，化合物10带有苯基含氰基。这两种化合物表现出良好的热稳定性和低带隙。化合物9和10的带隙分别为1.74和1.83电子伏特。这些结果表明它们是有潜力用于光电子学的材料。

  DOI：

  10.1139/cjc-2015-0542
• 作为产物：
  描述：

  溴代十二烷 在 正丁基锂 、 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 magnesium 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 生成 4-十二烷基-2-(4,4,5,5-四甲基-1,3,2-二氧硼戊环-2-基)噻吩
  参考文献：
  名称：

  Synthesis and characterization of acceptor–donor–acceptor-based low band gap small molecules containing benzoselenadiazole

  摘要：

  接受者-给体-接受者型化合物5′,5″-(苯并[c][1,2,5]硒唑二唑-4,7-二基)双(3′-十二烷基-2,2′-联噻吩-5-碳腈) (9) 和 4,4′-(5,5′-(苯并[c][1,2,5]硒唑二唑-4,7-二基)双(3-十二烷基噻吩-5,2-二基))二苯腈 (10) 被设计并合成。这些化合物在末端位置上有所不同，化合物9带有噻吩含氰基，化合物10带有苯基含氰基。这两种化合物表现出良好的热稳定性和低带隙。化合物9和10的带隙分别为1.74和1.83电子伏特。这些结果表明它们是有潜力用于光电子学的材料。

  DOI：

  10.1139/cjc-2015-0542

文献信息

• Thermoplastic Fluorescent Conjugated Polymers: Benefits of Preventing π-π Stacking
  作者：Chengjun Pan、Kazunori Sugiyasu、Yutaka Wakayama、Akira Sato、Masayuki Takeuchi

  DOI：10.1002/anie.201305728

  日期：2013.10.4

  Molecular wires: Fluorescent conjugated polymers that are sheathed within their own cyclic side chains have been synthesized (see picture). Owing to the unique three‐dimensional architecture, the polymers are light‐emissive, even in the film state, miscible, allowing the combination of various fluorescence colors, and thermoformable, like conventional plastics.

  分子线：合成了包覆在其自身环状侧链中的荧光共轭聚合物（参见图片）。由于具有独特的三维结构，这种聚合物即使在薄膜状态下也具有发光性，并且可以混溶，从而可以将各种荧光色组合在一起，并且可以像常规塑料一样进行热成型。
• NEAR-INFRARED ABSORBING DYE, OPTICAL FILTER, AND IMAGING DEVICE
  申请人：AGC Inc.

  公开号：US20210071004A1

  公开（公告）日：2021-03-11

  A near-infrared absorbing dye includes a compound represented by formula (A). Each of R 11 to R 14 is independently a hydrogen atom, a halogen atom, a hydroxyl group, or an alkyl, aryl or alaryl group. Each of pairs R 11 and R 12 , R 12 and R 13 , and R 13 and R 14 may combine with one another to form a monocyclic ring or a polycyclic ring in which from 2 to 4 rings are fused. Each of R 15 and R 16 is independently an alkyl or alaryl group. R 15 and R 16 may combine with one another to form a cyclohetero ring having from 5 to 10 members together with the nitrogen atom.

  一种近红外吸收染料包括由式（A）表示的化合物。R11至R14中的每一个独立地是氢原子、卤素原子、羟基或烷基、芳基或芳基烷基。R11和R12、R12和R13、以及R13和R14中的每一对可以相互结合形成一个单环或多环，其中有2至4个环融合。R15和R16中的每一个独立地是烷基或芳基烷基。R15和R16可以相互结合形成一个与氮原子一起具有5至10个成员的环杂环。
• Synthesis and properties of small band gap thienoisoindigo based conjugated polymers
  作者：Gijs W. P. Van Pruissen、Fatemeh Gholamrezaie、Martijn M. Wienk、René A. J. Janssen

  DOI：10.1039/c2jm34668k

  日期：——

  Using Stille and Suzuki polymerization reactions we incorporate thienoisoindigo (TII) as an acceptor co-monomer into a series of alternating π-conjugated copolymers with combinations of benzene, thiophene and carbazole as donor co-monomers. By changing the nature and length of the donor segments, the optical band gap of these soluble TII copolymers can be varied over a large range from 1.52 eV down to 0.87 eV. The semiconducting properties of the TII copolymers were established in bottom-gate bottom-contact field-effect transistors that provide hole mobilities for these materials in the range of 10−3 to 10−2 cm2 V−1 s−1.

  我们利用斯蒂尔（Stille）和铃木（Suzuki）聚合反应，将噻吩异靛蓝（TII）作为受体共聚单体，与苯、噻吩和咔唑作为供体共聚单体，结合成一系列交替π共轭共聚物。通过改变供体部分的性质和长度，这些可溶性TII共聚物的光带隙可以在1.52eV到0.87eV之间变化。TII共聚物的半导体特性在底部栅极底部接触场效应晶体管中得以确立，这些材料在10-3到10-2 cm2 V-1 s-1范围内的空穴迁移率。
• BENZODITHIOPHENE ORGANIC SEMICONDUCTIVE MATERIAL, PREPARATION METHOD AND USE THEREOF
  申请人：Ocean's King Lighting Science&Technology Co., Ltd.

  公开号：EP2615095B1

  公开（公告）日：2015-11-04
• Enhancing the Photocurrent in Diketopyrrolopyrrole-Based Polymer Solar Cells via Energy Level Control
  作者：Weiwei Li、W. S. Christian Roelofs、Martijn M. Wienk、René A. J. Janssen

  DOI：10.1021/ja305358z

  日期：2012.8.22

  A series of diketopyrrolopyrrole (DPP)-based small band gap polymers has been designed and synthesized by Suzuki or Stille polymerization for use in polymer solar cells. The new polymers contain extended aromatic pi-conjugated segments alternating with the DPP units and are designed to increase the free energy for charge generation to overcome current limitations in photocurrent generation of DPP-based polymers. In optimized solar cells with [6,6]phenyl-C-71-butyric acid methyl ester ([70]PCBM) as acceptor, the new DPP-polymers provide significantly enhanced external and internal quantum efficiencies for conversion of photons into collected electrons. This provides short-circuit current densities in excess of 16 mA cm(-2), higher than obtained so far, with power conversion efficiencies of 5.8% in simulated solar light. We analyze external and internal photon to collected electron quantum efficiencies for the new polymers as a function of the photon energy loss, defined as the offset between optical band gap and open circuit voltage, and compare the results to those of some of the best DPP-based polymers solar cells reported in the literature. We find that for the best solar cells there is an empirical relation between quantum efficiency and photon energy loss that presently limits the power conversion efficiency in these devices.