1,3-bis(2-thienyl)azulene | 245114-80-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: 1,3-bis(2-thienyl)azulene
• 英文别名: 1,3-di(2-thienyl)azulene；2-(3-thiophen-2-ylazulen-1-yl)thiophene
• CAS: 245114-80-1
• 化学式: C₁₈H₁₂S₂
• 分子量: 292.425
• InChiKey: HANCQEPHOYIKBH-UHFFFAOYSA-N

物化性质

• 熔点：
  131-133 °C
• 沸点：
  465.7±25.0 °C(Predicted)
• 密度：
  1.254±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  2
• 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：

  1,3-bis(2-thienyl)azulene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以15.6%的产率得到1,3-bis(5-bromo-2-thienyl)azulene
  参考文献：
  名称：

  Tuning the Semiconducting Behaviors of New Alternating Dithienyldiketopyrrolopyrrole–Azulene Conjugated Polymers by Varying the Linking Positions of Azulene

  摘要：

  Three new conjugated polymers DPPA1, DPPA2, and DPPA3 with dithienyldiketopyrrolopyrrole (DPP) and azulene moieties were synthesized and characterized. The five-membered rings of azulene are connected with DPP in DPPA1 and DPPA2, whereas the seven-membered ring of azulene is incorporated into the backbone of DPPA3. The LUMO energy of DPPA3, which was determined on the basis of the respective cyclic voltammograms and absorption spectra, is lower than those of DPPA1 and DPPA2. OFETs were successfully fabricated with thin films of DPPA1, DPPA2, and DPPA3. Thin films of DPPA1 and DPPA2 exhibit p-type semiconducting properties with hole mobilities up to 0.97 cm(2) V-1 s(-1), whereas typical ambipolar behavior is found for thin film of DPPA3 with hole and electron mobilities reaching 0.062 cm(2) V-1 s(-1) and 0.021 cm(2) V-1 s(-1), respectively. The results reveal that semiconducting properties of DPPA1, DPPA2, and DPPA3 can be tuned by varying the linkage positions of azulene with DPP moieties. Furthermore, DPPA1, DPPA2, and DPPA3 were tested preliminarily as photovoltaic materials. The power conversion efficiency (PCE) reaches 2.04% for the blending thin film DPPA1 with PC71BM.

  DOI：

  10.1021/acs.macromol.5b00158
• 作为产物：
  描述：

  Ethyl 3-(cyclohepta-1,3,5-trien-1-yl)-3-oxopropionate 在 palladium on activated charcoal 哌啶 、 盐酸 、 三氟甲磺酸三甲基硅酯 、 水 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二苯醚 、 二氯甲烷 、 苯 为溶剂， 反应 7.0h， 生成 1,3-bis(2-thienyl)azulene
  参考文献：
  名称：

  A Divergent Method for Preparing 1-Aryl- and 1,3-Diarylazulenes from Ethyl 3-(Cyclohepta-1,3,5-trien-1-yl)-3-oxopropionate

  摘要：

  DOI：

  10.1055/s-1999-3546

文献信息

• General Suzuki Coupling of Heteroaryl Bromides by Using Tri-<i>tert</i>-butylphosphine as a Supporting Ligand
  作者：Yinjun Zou、Guizhou Yue、Jianwei Xu、Jianrong Steve Zhou

  DOI：10.1002/ejoc.201402915

  日期：2014.9

  A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids.

  通过使用 Pd(OAc)2/PtBu3 作为催化剂，实现了主要家族杂芳基溴化物的快速 Suzuki 偶联的一般程序。许多偶联在室温下在正丁醇中几分钟内完成。与之前的研究不同，在各种杂芳基和芳基硼酸的偶联中系统地研究了三种典型的杂芳基溴化物。
• Stimuli-Responsive Conjugated Copolymers Having Electro-Active Azulene and Bithiophene Units in the Polymer Skeleton:  Effect of Protonation and p-Doping on Conducting Properties
  作者：Fuke Wang、Yee-Hing Lai、Ming-Yong Han

  DOI：10.1021/ma035335q

  日期：2004.5.1

  doping (p-doping) or protonation by TFA. The effects of p-doping and protonation on their conducting properties could be observed by UV−vis−NIR, EPR, SEM, and CV measurements, revealing different conducting mechanisms in p-doping and protonation. The EPR studies in particular confirmed the reversible protonation−deprotonation processes and high stability of the formed cation radicals at a p-doped or protonated

  通过氧化聚合合成了一系列在聚合物主链中包含烷基化联噻吩和电活性active烯的刺激响应共轭共聚物。这些共聚物以高收率形成，并在常见的有机溶剂（如氯仿，甲苯和THF）中具有良好的溶解性。它们还具有16 000至41 000的高分子量（M n），其结构与NMR，FTIR和元素分析表明的结构一致。这些共聚物具有高度的热稳定性和环境稳定性。像聚苯胺一样，这些azulene-thiophene共聚物可以被赋予高导电性（1-50 S cm -1）可通过两种途径进行：碘掺杂（p型掺杂）或TFA质子化。通过UV-vis-NIR，EPR，SEM和CV测量可以观察到p掺杂和质子化对其导电性能的影响，揭示了p掺杂和质子化中的不同导电机理。EPR研究特别证实了在p掺杂或质子化状态下可逆的质子去质子化过程和所形成阳离子自由基的高稳定性，表明它们在电子开关或抗氧化剂材料中的潜在应用。SEM研究表明，碘掺杂后会形成纳米
• Synthesis and properties of N,N,N′,N′-tetrasubstituted 1,3-bis(5-aminothien-2-yl)azulenes and their application as a hole-injecting material in organic light-emitting devices
  作者：Mitsunori Oda、Nguyen Chung Thanh、Masamichi Ikai、Hisayoshi Fujikawa、Keita Nakajima、Shigeyasu Kuroda

  DOI：10.1016/j.tet.2007.08.016

  日期：2007.10

  Two title compounds, N,N,N',N'-tetraphenyl-1,3-bis(5-aminothien-2-yl)azulene (3a) and 1,3-bis5-(9-carbazolyl)thien-2-yl}azulene (3b), were synthesized from 1,3-di(2-thienyl)azulene (4) by a two-step sequence involving bromination and subsequent Pd-catalyzed amination. These compounds were characterized by spectroscopic analyses and the structure of 3a was determined by X-ray crystallographic analysis. Their HOMO energy levels were estimated using their electrochemical oxidation potentials, and these compounds were used as a hole-injecting material in organic light-emitting devices. The device with 3a showed greater durability than that with copper phthalocyanine. (C) 2007 Elsevier Ltd. All rights reserved.
• A Divergent Method for Preparing 1-Aryl- and 1,3-Diarylazulenes from Ethyl 3-(Cyclohepta-1,3,5-trien-1-yl)-3-oxopropionate
  作者：Mitsunori Oda

  DOI：10.1055/s-1999-3546

  日期：1999.8
• Tuning the Semiconducting Behaviors of New Alternating Dithienyldiketopyrrolopyrrole–Azulene Conjugated Polymers by Varying the Linking Positions of Azulene
  作者：Jingjing Yao、Zhengxu Cai、Zitong Liu、Chenmin Yu、Hewei Luo、Yang Yang、Sifen Yang、Guanxin Zhang、Deqing Zhang

  DOI：10.1021/acs.macromol.5b00158

  日期：2015.4.14

  Three new conjugated polymers DPPA1, DPPA2, and DPPA3 with dithienyldiketopyrrolopyrrole (DPP) and azulene moieties were synthesized and characterized. The five-membered rings of azulene are connected with DPP in DPPA1 and DPPA2, whereas the seven-membered ring of azulene is incorporated into the backbone of DPPA3. The LUMO energy of DPPA3, which was determined on the basis of the respective cyclic voltammograms and absorption spectra, is lower than those of DPPA1 and DPPA2. OFETs were successfully fabricated with thin films of DPPA1, DPPA2, and DPPA3. Thin films of DPPA1 and DPPA2 exhibit p-type semiconducting properties with hole mobilities up to 0.97 cm(2) V-1 s(-1), whereas typical ambipolar behavior is found for thin film of DPPA3 with hole and electron mobilities reaching 0.062 cm(2) V-1 s(-1) and 0.021 cm(2) V-1 s(-1), respectively. The results reveal that semiconducting properties of DPPA1, DPPA2, and DPPA3 can be tuned by varying the linkage positions of azulene with DPP moieties. Furthermore, DPPA1, DPPA2, and DPPA3 were tested preliminarily as photovoltaic materials. The power conversion efficiency (PCE) reaches 2.04% for the blending thin film DPPA1 with PC71BM.