2,2'-diethynyl-3,3'-dihexyl-5,5'-bithiophene | 256345-26-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 2,2'-diethynyl-3,3'-dihexyl-5,5'-bithiophene
• 英文别名: 2-Ethynyl-5-(5-ethynyl-4-hexylthiophen-2-yl)-3-hexylthiophene
• CAS: 256345-26-3
• 化学式: C₂₄H₃₀S₂
• 分子量: 382.634
• InChiKey: SJZCIVFHYIHHJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2,2'-diethynyl-3,3'-dihexyl-5,5'-bithiophene 、 5-ethynyl-2,3,7,8,12,13,17,18-octaethylporphyrinatopalladium(II) 生成 5,5'-bis{4-[2,3,7,8,12,13,17,18-octaethylporphyrinatopalladium(II)-5'-yl]-1,3-butadiynyl}-4,4'-dihexyl-2,2'-bithiophene
  参考文献：
  名称：

  Synthesis and properties of unsymmetrically extended π-electronic conjugation system of octaethylporphyrin(Ni)–dihexybithiophene–octaethylporphyrin(Pd) connected with diacetylene linkage

  摘要：

  Orientational isomers of the diacetylene-group connected dihexybithiophene (DHBTh) derivatives have been synthesized. in which the different octaethylporphyrin (OEP(M): M=Ni or Pd) rings are attached at the ends. Reflecting the unsymmetrical structural feature, the peculiar electronic properties of the extended OEP(Ni)-DHBTh-OEP(Pd) system were observed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01839-2
• 作为产物：
  描述：

  2-溴-3-己基噻吩 在 potassium fluoride 、 copper(l) iodide 、 二(氰基苯)二氯化钯 、 四(三苯基膦)钯 、 silver nitrate 、 三乙胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 36.17h， 生成 2,2'-diethynyl-3,3'-dihexyl-5,5'-bithiophene
  参考文献：
  名称：

  Electroactive Dyes Based on 1,8‐Naphthalimide with Acetylene Linkers as Promising OLED Materials – the Relationship Between Structure and Photophysical Properties

  摘要：

  摘要 成功合成了四种具有 1,8-萘二甲酰亚胺基团的 A-π-D-π-A 型有机小分子。所设计的化合物由两个 1,8-萘二甲酰亚胺单元通过乙炔基 π 链接与选定的功能化供体基团（即 2,2'-联噻吩荧光基团）连接而成。2,2'-联噻吩、芴、吩噻嗪和咔唑衍生物。基于 Sonogashira 交叉偶联的合成方法使我们能够以良好的收率获得所介绍的染料。我们对所得到的对称小分子的光学、电化学和热学特性进行了深入研究，并证明了它们在 OLED 设备中的潜在应用性。此外，还通过实验和理论研究探讨了分子结构与性能之间的关系。由于使用了不同的供体基团，因此可以实现从绿光（DEV4）到橙红光（DEV3）的高效电致发光，其中 DEV4 的最大亮度为 3 820 cd/m2。在设计的分子中加入乙炔连接物后，D 和 A 片段可以自由旋转，从而在整个分子中实现有效的 π 电子通信，这一点已通过 DFT 研究得到证实。所获得的染料具有高热稳定性、可逆的氧化还原过程、令人满意的光电特性以及在有机溶剂中的良好溶解性等特点，非常适合应用于小分子有机发光二极管（SM-OLED）技术。

  DOI：

  10.1002/chem.202302115

文献信息

• Synthesis and Properties of Head-to-head, Head-to-tail, and Tail-to-tail Orientational Isomers of Extended Dihexylbithiophene–Octaethylporphyrin System [OEP–(DHBT)_<i>n</i>–OEP] Connected with 1,3-Butadiyne Linkages
  作者：Hiroyuki Higuchi、Takashi Ishikura、Kazumine Mori、Yukari Takayama、Koji Yamamoto、Keita Tani、Keiko Miyabayashi、Mikio Miyake

  DOI：10.1246/bcsj.74.889

  日期：2001.5

  An extended π-electronic conjugation system of dihexylbithiophene–octaethylporphyrin [OEP–(DHBT)n–OEP; n = 1–5], all the chromophores in which are connected with the linkage of 1,3-butadiyne (diacetylene), was synthesized by an oxidative cross-coupling reaction of the corresponding terminal acetylenes. Absorption spectral and electrochemical properties of the OEP–(DHBT)n–OEP system were examined. The results proved that the orientation of two 3-hexylthiophene (3HTh) rings of DHBT plays an important role in electronic communications between the two terminal OEP rings.

  二己基联噻吩-八乙基卟啉的扩展 π 电子共轭体系 [OEP-(DHBT)n-OEP； n = 1–5]，其中所有发色团均与 1,3-丁二炔（丁二炔）键连接，通过相应末端乙炔的氧化交叉偶联反应合成。检查了 OEP-(DHBT)n-OEP 系统的吸收光谱和电化学性质。结果证明DHBT的两个3-己基噻吩(3HTh)环的取向在两个末端OEP环之间的电子通信中起着重要作用。
• Syntheses and electronic properties of the nickel and palladium complexes of the octaethylporphyrin(M1)–(dihexylbithiophene) n –octaethylporphyrin(M2) system [OEP(M1)–(DHBTh) n –OEP(M2)] connected with the diacetylene linkage. A methodology for molecular design of the particular electronic structure
  作者：Naoto Hayashi、Miho Murayama、Kazumine Mori、Akihito Matsuda、Emiko Chikamatsu、Keita Tani、Keiko Miyabayashi、Mikio Miyake、Hiroyuki Higuchi

  DOI：10.1016/j.tet.2004.04.064

  日期：2004.7

  The palladium complexes of highly extended pi-electronic conjugation system, octaethyl porphyrin (Pd)-(dihexylbithiophene)(n)-octaethylporphyrin(Pd) [OEP(Pd)-(DHBTh)(n)-OEP(Pd), n=1-6], were synthesized, in which all the chromophores are connected with diacetylene linkage. The unsymmetrical derivatives of OEP(Ni)-DHBTh-OEP(Pd) were also successfully synthesized. Electronic properties of these symmetrical and unsymmetrical complexes were conclusively described, as compared with those of OEP(Ni)(DHBTh)(n)-OEP(Ni). Based on the structure elements, a methodical guiding principle for molecular design of the particular electronic structure will be proposed. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and properties of orientational isomers of hybridized dihexylbithiopheneoctaethylporphyrin connected with 1,3-butadiyne linkages
  作者：Hiroyuki Higuchi、Takashi Ishikura、Keiko Miyabayashi、Mikio Miyake、Koji Yamamoto

  DOI：10.1016/s0040-4039(99)01929-2

  日期：1999.12

  A new type of hybridized dihexylbithiophene-octaethylporphyrin derivative (DHBT-OEP) connected with the 1,3-butadiyne linkage was synthesized by oxidative cross-coupling of the corresponding terminal acetylenes. The absorption spectra and electrochemical properties of the DHBT-OEP hybrid were examined, clearly proving that the orientation of two 3-hexylthiophene rings of DHBT plays an important role in electronic communication between the two terminal OEP rings. (C) 1999 Elsevier Science Ltd. All rights reserved.