2,6-dibromonaphtho<1,8-bc:5,4-b'c'>dithiophene | 158362-54-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,6-dibromonaphtho<1,8-bc:5,4-b'c'>dithiophene
• 英文别名: 2,6-dibromonaphtho[1,8-bc:5,4-b'c']dithiophene；3,9-Dibromo-2,8-dithiatetracyclo[5.5.2.04,13.010,14]tetradeca-1(13),3,5,7(14),9,11-hexaene
• CAS: 158362-54-0
• 化学式: C₁₂H₄Br₂S₂
• 分子量: 372.104
• InChiKey: UEEZKQGVUFGUHD-UHFFFAOYSA-N

物化性质

• 沸点：
  479.7±40.0 °C(predicted)
• 密度：
  2.147±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(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：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,6-dibromonaphtho<1,8-bc:5,4-b'c'>dithiophene 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以61%的产率得到naphtho<1,8-bc:5,4-b'c'>dithiophene
  参考文献：
  名称：

  Synthesis, Structures, and Properties of Two Isomeric Naphthodithiophenes and Their Methyl, Methylthio, and 2-Thienyl Derivatives; Application to Conductive Charge-Transfer Complexes and Low-Bandgap Polymers

  摘要：

  我们成功合成了与芘同电子体的两种异构萘二噻吩（syn-NDT 和 anti-NDT）及其二甲基、双（甲硫基）和二（2-噻吩基）衍生物，它们是新型近融合杂芳香族化合物。其中，母体 syn-NDT 和反 NDT 的二(2-噻吩基)衍生物通过 X 射线晶体学分析进行了研究，结果表明其分子结构由相当平面但有相当应变的骨架环组成，晶体结构的特征是均匀堆叠柱的人字形排列。与芘相比，这些杂芳香族化合物的紫外/可见光谱显示出相当大的π-π*转变红移，使它们成为从黄色到紫色的发色剂。循环伏安法表明，它们的电子捐赠能力比芘强得多。因此，除甲基衍生物外，它们都能与碘和 DDQ 形成高导电性分子络合物。此外，母体萘二硫基噻吩和二（2-噻吩基）衍生物的电化学氧化会导致导电聚合物的形成，这些聚合物在未掺杂时显示出较低的 HOMO-LUMO 带隙。特别是 syn-NDT 和 anti-NDT 聚合物的带隙都非常低，约为 0.8 eV（77 kJ mol-1）。

  DOI：

  10.1246/bcsj.75.1795
• 作为产物：
  描述：

  tetramethyl 5,5'-dibromo-2,2'-diformyl-3,3'-bithiophene-4,4'-diylbis(methylphosphonate) 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以22%的产率得到2,6-dibromonaphtho<1,8-bc:5,4-b'c'>dithiophene
  参考文献：
  名称：

  Naphtho[1,8-bc : 5,4-b′c′]dithiophene: a new heteroarene isoelectronic with pyrene

  摘要：

  制备出的标题化合物是一种与芘具有等电子性的新型杂芳香族化合物，其电子捐赠能力强于芘和异构萘[1,8-bc : 4,5-bâ²câ²]二噻吩。

  DOI：

  10.1039/c39940001859

文献信息

• 2,6-Diarylnaphtho[1,8-<i>bc</i>:5,4-<i>b</i><i>‘</i><i>c</i><i>‘</i>]dithiophenes as New High-Performance Semiconductors for Organic Field-Effect Transistors
  作者：Kazuo Takimiya、Yoshihito Kunugi、Yuta Toyoshima、Tetsuo Otsubo

  DOI：10.1021/ja043429p

  日期：2005.3.1

  A series of 2,6-diaryl-substituted naphtho[1,8-bc:5,4-b'c]dithiophene derivatives 2-6, whose aryl groups include 5-hexyl-2-thienyl, 2,2'-bithiophen-5-yl, phenyl, 2-naphthyl, and 4-biphenylyl, was synthesized by the palladium-catalyzed Suzuki-Miyaura coupling and utilized as active layers of organic field-effect transistors (OFETs). All devices fabricated using vapor-deposited thin films of these compounds showed typical p-type FET characteristics. The mobilities are relatively good and widely range from 10(-4) to 10(-1) cm(2) V-1 s(-1), depending on the substituent groups. Among them, the mobilities of the devices using films of 3-5 tend to increase with the increasing temperature of the Si/SiO2 substrate during film deposition. In particular, the device based on the naphthyl derivative 5, when fabricated at 140 degrees C, marked a high mobility of 0.11 cm(2) V-1 s(-1) with an on/off ratio of 10(5), which is a top class of performance among organic thin-film transistors. Studies of X-ray diffractograms (XRDs) have revealed that the film of 4 and 5 is composed of two kinds of crystal grains with different phases, so-called "single-crystal phase" and "thin film phase", and that the proportion of the thin film phase increases with an increase of the substrate temperature. In the thin film phase the assembled molecules stand nearly upright on the substrate in such a way as to be favorable to carrier migration.
• Takimiya Kazuo, Otsubo Tetsuo, Ogura Fumio, J. Chem. Soc. Chem. Commun, (1994) N 16, S 1859-1860
  作者：Takimiya Kazuo, Otsubo Tetsuo, Ogura Fumio

  DOI：——

  日期：——
• Synthesis, Structures, and Properties of Two Isomeric Naphthodithiophenes and Their Methyl, Methylthio, and 2-Thienyl Derivatives; Application to Conductive Charge-Transfer Complexes and Low-Bandgap Polymers
  作者：Kazuo Takimiya、Ken-ichi Kato、Yoshio Aso、Fumio Ogura、Tetsuo Otsubo

  DOI：10.1246/bcsj.75.1795

  日期：2002.8

  Two isomeric naphthodithiophenes (syn-NDT and anti-NDT), isoelectronic with pyrene, as well as their dimethyl, bis(methylthio), and di(2-thienyl) derivatives have been successfully synthesized as novel peri-fused heteroaromatics. Among them, the parent syn-NDT and the di(2-thienyl) derivative of anti-NDT were examined by X-ray crystallographic analyses, revealing that the molecular structures comprise fairly planar, but considerably strained skeletal rings, and their crystal structures are characterized by a herringbone arrangement of uniform stacking columns. The UV/vis spectra of these heteroaromatics show considerable red-shifts of the π–π* transitions as compared to that of pyrene, making them chromogens ranging from yellow to purple. Cyclic voltammetry indicates that they have much stronger electron donating abilities than pyrene. Consequently, all of them, except for the methyl derivatives, can form highly conductive molecular complexes with iodine and DDQ. In addition, the electrochemical oxidation of the parent naphthodithiophenes and the di(2-thienyl) derivatives leads to the formation of conductive polymers, which show low HOMO–LUMO bandgaps upon undoping. In particular, both polymers of syn-NDT and anti-NDT have very low bandgaps of ca. 0.8 eV (77 kJ mol−1).

  我们成功合成了与芘同电子体的两种异构萘二噻吩（syn-NDT 和 anti-NDT）及其二甲基、双（甲硫基）和二（2-噻吩基）衍生物，它们是新型近融合杂芳香族化合物。其中，母体 syn-NDT 和反 NDT 的二(2-噻吩基)衍生物通过 X 射线晶体学分析进行了研究，结果表明其分子结构由相当平面但有相当应变的骨架环组成，晶体结构的特征是均匀堆叠柱的人字形排列。与芘相比，这些杂芳香族化合物的紫外/可见光谱显示出相当大的π-π*转变红移，使它们成为从黄色到紫色的发色剂。循环伏安法表明，它们的电子捐赠能力比芘强得多。因此，除甲基衍生物外，它们都能与碘和 DDQ 形成高导电性分子络合物。此外，母体萘二硫基噻吩和二（2-噻吩基）衍生物的电化学氧化会导致导电聚合物的形成，这些聚合物在未掺杂时显示出较低的 HOMO-LUMO 带隙。特别是 syn-NDT 和 anti-NDT 聚合物的带隙都非常低，约为 0.8 eV（77 kJ mol-1）。
• Naphtho[1,8-bc : 5,4-b′c′]dithiophene: a new heteroarene isoelectronic with pyrene
  作者：Kazuo Takimiya、Tetsuo Otsubo、Fumio Ogura

  DOI：10.1039/c39940001859

  日期：——

  The title compound is prepared as a new heteroarene isoelectronic with pyrene, having a stronger electron donating ability than pyrene and isomeric naphtho[1,8-bc : 4,5-b′c′]dithiophene.

  制备出的标题化合物是一种与芘具有等电子性的新型杂芳香族化合物，其电子捐赠能力强于芘和异构萘[1,8-bc : 4,5-bâ²câ²]二噻吩。