5,5'-diethynyl-3,3'-dihexyl-2,2'-bithiophene | 256345-25-2

• 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: 5,5'-diethynyl-3,3'-dihexyl-2,2'-bithiophene
• 英文别名: 5-Ethynyl-2-(5-ethynyl-3-hexylthiophen-2-yl)-3-hexylthiophene
• CAS: 256345-25-2
• 化学式: C₂₄H₃₀S₂
• 分子量: 382.634
• InChiKey: VULAPCKTPFDFGH-UHFFFAOYSA-N

物化性质

• 沸点：
  518.5±50.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

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：

  5,5'-diethynyl-3,3'-dihexyl-2,2'-bithiophene 、 5-ethynyl-2,3,7,8,12,13,17,18-octaethylporphyrinatopalladium(II) 生成
  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：

  5,5'-二溴-3,3'-二己基-2,2'-并噻吩 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 作用下， 以 甲醇 、 正己烷 为溶剂， 反应 10.0h， 生成 5,5'-diethynyl-3,3'-dihexyl-2,2'-bithiophene
  参考文献：
  名称：

  Synthesis and Properties of Head-to-head, Head-to-tail, and Tail-to-tail Orientational Isomers of Extended Dihexylbithiophene–Octaethylporphyrin System [OEP–(DHBT)_n–OEP] Connected with 1,3-Butadiyne Linkages

  摘要：

  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。

  DOI：

  10.1246/bcsj.74.889

文献信息

• Conjugated D–A porphyrin dimers for solution-processed bulk-heterojunction organic solar cells
  作者：Tianqi Lai、Xuebin Chen、Liangang Xiao、Lin Zhang、Tianxiang Liang、Xiaobin Peng、Yong Cao

  DOI：10.1039/c7cc00489c

  日期：——

  Three porphyrin dimers with different linkages are synthesized as donors for organic photovoltaics with an optimized PCE of 6.42%.

  合成了三种具有不同连接的卟啉二聚体作为有机光伏的给体，其最优化的光电转换效率为6.42%。
• Group 14 Dithienometallole-Linked Ethynylene-Conjugated Porphyrin Dimers
  作者：Mitsuhiko Morisue、Yuki Hoshino、Masashi Nakamura、Takashi Yumura、Shinjiro Machida、Yousuke Ooyama、Masaki Shimizu、Joji Ohshita

  DOI：10.1021/acs.inorgchem.6b00667

  日期：2016.8.1

  The considerably conjugated π systems of the group 14 dithienometallole-linked ethynylene-conjugated porphyrin dimers (1Ms) were described based on comprehensive experimental and theoretical studies. The electronic absorption spectra of 1M displayed a large splitting in the Soret band and a red-shifted Q-band, indicating that the dithienometallole spacer was effective in facilitating the porphyrin–porphyrin

  在全面的实验和理论研究的基础上，描述了第14组二硫杂金属原子连接的乙炔基共轭卟啉二聚体（1M s）的显着共轭π系统。1M的电子吸收光谱在Soret谱带中出现了较大的分裂，并在Q谱带中出现了红移，表明二硫代金属氟间隔基可有效促进卟啉-卟啉的电子偶联。1M的扭转平面化行为在时间分辨荧光光谱中观察到。密度泛函理论（DFT）计算表明，二硫杂金属基间隔物是乙炔共轭卟啉的理想配偶体，由于它们相似的HOMO和LUMO水平，它们可产生完全离域的最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）。 。最后，当处于光激发状态时，1M在二硫代金属氟间隔基中表现出强烈的喹诺酮-Cumulenic共轭趋势。
• Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions
  作者：Karolis Leitonas、Brigita Vigante、Dmytro Volyniuk、Audrius Bucinskas、Pavels Dimitrijevs、Sindija Lapcinska、Pavel Arsenyan、Juozas Vidas Grazulevicius

  DOI：10.3762/bjoc.19.139

  日期：——

  gained significant attention in the field of materials chemistry, particularly in the development of heavy-metal-free pure organic light-emitting diodes (OLEDs). Extensive research on organic compounds exhibiting thermally activated delayed fluorescence (TADF) has led to numerous patents and research articles. This study focuses on the synthesis and investigation of the semiconducting properties of polyaromatic

  抽象的 吡啶-3,5-二甲腈部分在材料化学领域引起了极大的关注，特别是在不含重金属的纯有机发光二极管（OLED）的开发中。对具有热激活延迟荧光 (TADF) 的有机化合物的广泛研究已经产生了大量专利和研究文章。本研究重点是含有两个和三个吡啶-2,6-二咔唑基-3,5-二甲腈片段的聚芳香π-系统的合成和半导体性能研究。这些化合物通过 Sonogashira 偶联反应合成，并通过稳态和时间分辨发光光谱进行表征。这些化合物表现出从供体到受体的有效分子内电荷转移（ICT）。化合物溶液的光致发光（PL）光谱在可见光区域显示出非结构发射峰，这归因于ICT发射。化合物溶液的PL强度在脱氧后增强，这表明TADF。化合物的光致发光量子产率和TADF性质对介质敏感。循环伏安法测量表明由于其高电离势而具有良好的空穴阻挡和电子注入特性。光电子能谱和飞行时间测量揭示了其中一种化合物具有良好的电子传输特性。一般来说，具有吡啶-3
• 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.