1,3-bis(5-bromo-2-thienyl)azulene | 956591-41-6

• 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(5-bromo-2-thienyl)azulene
• 英文别名: 1,3-bis(5-bromothiophen-2-yl)azulene；2-Bromo-5-[3-(5-bromothiophen-2-yl)azulen-1-yl]thiophene；2-bromo-5-[3-(5-bromothiophen-2-yl)azulen-1-yl]thiophene
• CAS: 956591-41-6
• 化学式: C₁₈H₁₀Br₂S₂
• 分子量: 450.217
• InChiKey: HIVMNVUAULDMPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  22
• 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(5-bromo-2-thienyl)azulene 、 咔唑 在 palladium diacetate sodium t-butanolate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以35%的产率得到1,3-bis{5-(9-carbazolyl)thien-2-yl}azulene
  参考文献：
  名称：

  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

  摘要：

  Two title compounds, N,N,N',N'-tetraphenyl-1,3-bis(5-aminothien-2-yl)azulene (3a) and 1,3-bis{5-(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.

  DOI：

  10.1016/j.tet.2007.08.016
• 作为产物：
  描述：

  1,3-二碘甘菊蓝 在 四(三苯基膦)钯 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 cesium fluoride 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1,3-bis(5-bromo-2-thienyl)azulene
  参考文献：
  名称：

  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

  摘要：

  Two title compounds, N,N,N',N'-tetraphenyl-1,3-bis(5-aminothien-2-yl)azulene (3a) and 1,3-bis{5-(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.

  DOI：

  10.1016/j.tet.2007.08.016

文献信息

• 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.
• 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.