4,7-dibromo-4'-tert-butylspiro[1,3-benzodiazole-2,1'-cyclohexane] | 1372784-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4,7-dibromo-4'-tert-butylspiro[1,3-benzodiazole-2,1'-cyclohexane]
• 英文别名: 4,7-dibromo-4'-(tert-butyl)spiro[benzo[d]imidazole-2,1'-cyclohexane]；4,7-Dibromo-4'-tert-butylspiro[benzimidazole-2,1'-cyclohexane]；4,7-dibromo-4'-tert-butylspiro[benzimidazole-2,1'-cyclohexane]
• CAS: 1372784-41-2
• 化学式: C₁₆H₂₀Br₂N₂
• 分子量: 400.156
• InChiKey: VRVRQPTTXHYYLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,7-dibromo-4'-tert-butylspiro[1,3-benzodiazole-2,1'-cyclohexane] 、 (噻吩并[3,2-B]噻吩-2-基)三丁基锡 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以50%的产率得到4'-tert-butyl-4,7-bis(thieno[3,2-b]thiophen-2-yl)spiro[benzodiazole-2,1'-cyclohexane]
  参考文献：
  名称：

  在所有氧化还原状态下均具有高光学透明性：苯并咪唑和噻吩并[3,2-b]噻吩的共轭聚合物的合成与表征

  摘要：

  基于苯并咪唑和噻吩并[3,2-b]噻吩部分，4'-叔丁基-4,7-二（噻吩并[3,2-b]噻吩-2-基）螺[据报道苯并[d]咪唑-2，1'-环己烷]（TTBI）及其电化学聚合。对该聚合物进行了电化学和光谱电化学研究。氧化和还原过程中的高光学透明性和低着色效率使该聚合物成为发光二极管和光电器件以及电致变色器件的对电极中空穴注入层的理想候选者。

  DOI：

  10.1016/j.electacta.2012.08.050
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 sodium tetrahydroborate 、 氢溴酸 、 溴 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 28.0h， 生成 4,7-dibromo-4'-tert-butylspiro[1,3-benzodiazole-2,1'-cyclohexane]
  参考文献：
  名称：

  Synthesis and electrochemical properties of a new benzimidazole derivative as the acceptor unit in donor–acceptor–donor type polymers

  摘要：

  A new benzimidazole unit, 4'-(tert-butyl)spiro[benzo[d]imidazole-2,1'-cyclohexane] was synthesized and coupled with different donor units like 3-hexylthiophene and 3,4-ethylenedioxythiophene (EDOT) via Stille coupling. The donor-acceptor-donor (D-A-D) type monomers, 4'-(tert-butyl)-4,7-bis(4-hexylthiophen-2-yl)spiro[benzo[d]imidazole-2,1'-cyclohexane] (BIHT) and 4'-(tert-butyl)-4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)spiro[benzo[d]imidazole-2,1'-cyclohexane] (BIED) were electrochemically polymerized, their electrochemical and optical properties were investigated by cyclic voltammetry, UV-vis-NIR spectroscopy techniques. Effect of donor groups on the optical and electronic properties of polymer was studied. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.electacta.2012.02.047

文献信息

• Synthesis and electrochemical properties of a new benzimidazole derivative as the acceptor unit in donor–acceptor–donor type polymers
  作者：Ali Can Ozelcaglayan、Merve Sendur、Naime Akbasoglu、Dogukan Hazar Apaydin、Ali Cirpan、Levent Toppare

  DOI：10.1016/j.electacta.2012.02.047

  日期：2012.4

  A new benzimidazole unit, 4'-(tert-butyl)spiro[benzo[d]imidazole-2,1'-cyclohexane] was synthesized and coupled with different donor units like 3-hexylthiophene and 3,4-ethylenedioxythiophene (EDOT) via Stille coupling. The donor-acceptor-donor (D-A-D) type monomers, 4'-(tert-butyl)-4,7-bis(4-hexylthiophen-2-yl)spiro[benzo[d]imidazole-2,1'-cyclohexane] (BIHT) and 4'-(tert-butyl)-4,7-bis(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)spiro[benzo[d]imidazole-2,1'-cyclohexane] (BIED) were electrochemically polymerized, their electrochemical and optical properties were investigated by cyclic voltammetry, UV-vis-NIR spectroscopy techniques. Effect of donor groups on the optical and electronic properties of polymer was studied. (C) 2012 Elsevier Ltd. All rights reserved.
• High optical transparency in all redox states: Synthesis and characterization of benzimidazole and thieno[3,2-b]thiophene containing conjugated polymers
  作者：Buket Zaifoglu、Merve Sendur、Naime Akbasoglu Unlu、Levent Toppare

  DOI：10.1016/j.electacta.2012.08.050

  日期：2012.12

  The synthesis of a novel monomer based on benzimidazole and thieno[3,2-b]thiophene moieties, 4′-tert-butyl-4,7-di(thieno[3,2-b]thiophen-2-yl)spiro[benzo[d]imidazole-2,1′-cyclohexane] (TTBI), and its electrochemical polymerization are reported. Electrochemical and spectroelectrochemical studies of the polymer were investigated. The high optical transparency and low coloration efficiency during oxidation

  基于苯并咪唑和噻吩并[3,2-b]噻吩部分，4'-叔丁基-4,7-二（噻吩并[3,2-b]噻吩-2-基）螺[据报道苯并[d]咪唑-2，1'-环己烷]（TTBI）及其电化学聚合。对该聚合物进行了电化学和光谱电化学研究。氧化和还原过程中的高光学透明性和低着色效率使该聚合物成为发光二极管和光电器件以及电致变色器件的对电极中空穴注入层的理想候选者。