4-(3,4-ethylenedioxythiophene-70-yl)-7-(thiophen-2-yl)-2,1,3-benzothiadiazole | 1257420-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻二唑类
• 英文名称: 4-(3,4-ethylenedioxythiophene-70-yl)-7-(thiophen-2-yl)-2,1,3-benzothiadiazole
• 英文别名: 4-(3,4-ethylenedioxythiophene-2-yl)-7-(thiophen-2-yl)-2,1,3-benzothiadiazole；EDBTT；4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-7-(thiophen-2-yl)benzo[c][1,2,5]thiadiazole；4-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-5-yl)-7-thiophen-2-yl-2,1,3-benzothiadiazole；4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-7-thiophen-2-yl-2,1,3-benzothiadiazole
• CAS: 1257420-10-2
• 化学式: C₁₆H₁₀N₂O₂S₃
• 分子量: 358.466
• InChiKey: DHVXWQMUSXKSOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-(3,4-ethylenedioxythiophene-70-yl)-7-(thiophen-2-yl)-2,1,3-benzothiadiazole 、 1,3-二溴-5-己基-4H-噻吩并[3,4-C]吡咯-4,6(5H)-二酮 在 四丁基溴化铵 、 potassium acetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以37%的产率得到
  参考文献：
  名称：

  合成用于有机光伏的基于[A'（D'AD）2 ]的推拉小分子的简便方法†

  摘要：

  利用C–H键与Pd（AcO）2 /的选择性直接杂芳基化反应，首次开发了一种有效的合成一系列基于[A'（D'AD）2 ]结构的小分子的途径。Bu 4 NBr简单催化体系。不对称化合物4-（2,3-二氢噻吩并[3,4- b ] [1,4]二恶英-5-基）-7-（噻吩-2-基）苯并[ c ] [的CH芳基化1,2,5]噻二唑（5）表明，乙基二氧噻吩部分中的（C5）比其噻吩单元中的对应物对CH芳基化反应更具活性。新的小分子带有两个不同的受体和/或供体，从而减小了电子带隙并提高了推挽系统的强度以及分子内电荷从供体转移到受体单元的数量。内酰胺和含酰亚胺的受体由于其良好的共轭结构，强大的π-π相互作用和高电子亲和力以及它们在光伏共轭材料中作为电子吸收单元的潜力而被用作第二个电子吸收单元。所有小分子均显示宽吸收光谱和光学带隙，估计在1.72–1.29 eV范围内。从循环伏安法，V oc）。EHID（EDBTT）2：PC

  DOI：

  10.1039/c5ra06660c
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 bis-triphenylphosphine-palladium(II) chloride 、 氢溴酸 、 溴 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 4-(3,4-ethylenedioxythiophene-70-yl)-7-(thiophen-2-yl)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  Combination of donor characters in a donor–acceptor–donor (DAD) type polymer containing benzothiadiazole as the acceptor unit

  摘要：

  benzothiadiazole bearing donor-acceptor-donor (D-A-D) type monomer (M-3) was synthesized using the combination of 3, 4-ethylenedioxythiophene (EDOT) and thiophene donor units to understand the effect of donor strength on the optoelectronic and electrochemical properties. The resulting monomer was polymerized electrochemically (P-3) and compared with its symmetrical thiophene (P-1) and EDOT (P-2) bearing homologues whether there exists a combination of the electrochemical and optical characteristics. Also, copolymer studies were performed with symmetrical thiophene (M-1) and EDOT (M-2) containing monomers in order to compare the results with P-3. Cyclic voltammetry (CV) and spectro-electrochemistry results revealed that P-3 is a low band gap polymer (1.18 eV) having both p-and n-type property which is superior to the copolymers synthesized using M-1 and M-2. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.orgel.2010.09.001

文献信息

• 전자 도너-억셉터가 도입된 저분자 유기 화합물 및 이의 합성방법, 이를 이용한 유기 광전자 소자
  申请人：Gwangju Institute of Science and Technology 광주과학기술원(319980993815) BRN ▼410-82-07550

  公开号：KR20160146563A

  公开（公告）日：2016-12-21

  전자 도너-억셉터가 도입된 저분자 유기 화합물 및 이의 합성방법, 이를 이용한 유기 광전자 소자를 제공한다. 본 발명은 화학식 1로 표시되는 전자 도너-억셉터가 도입된 신규한 저분자 유기물을 제공한다. 본 발명에 따르면, Pd(OAc)/BuNBr 촉매 시스템 하에서 강한 푸쉬-풀(push-pull) 도너-억셉터 시스템을 가진 [A`(D`AD)] 구조의 저분자 유기물을 용이하게 합성할 수 있다. 이러한 [A`(D`AD)] 구조를 가진 저분자 유기물을 유기 광전 소자 내 활성층으로 이용함으로써, 높은 분자내 전하 전달(ICT)를 제공하고 높은 단락 전류(Jsc)를 제공할 수 있다.

  本发明提供了引入电子供体-受体的新型低分子有机物和其合成方法，以及利用其制备有机光电子器件。根据本发明，可以在Pd（OAc）/BuNBr催化体系下容易地合成具有强烈推-拉（push-pull）电子供体-受体系统的[A`（D`AD）]结构的低分子有机物。通过将具有此类[A`（D`AD）]结构的低分子有机物用作有机光电池的活性层，可以提供高分子内电荷传递（ICT）和高短路电流（Jsc）。
• Combination of donor characters in a donor–acceptor–donor (DAD) type polymer containing benzothiadiazole as the acceptor unit
  作者：Merve Sendur、Abidin Balan、Derya Baran、Baris Karabay、Levent Toppare

  DOI：10.1016/j.orgel.2010.09.001

  日期：2010.12

  benzothiadiazole bearing donor-acceptor-donor (D-A-D) type monomer (M-3) was synthesized using the combination of 3, 4-ethylenedioxythiophene (EDOT) and thiophene donor units to understand the effect of donor strength on the optoelectronic and electrochemical properties. The resulting monomer was polymerized electrochemically (P-3) and compared with its symmetrical thiophene (P-1) and EDOT (P-2) bearing homologues whether there exists a combination of the electrochemical and optical characteristics. Also, copolymer studies were performed with symmetrical thiophene (M-1) and EDOT (M-2) containing monomers in order to compare the results with P-3. Cyclic voltammetry (CV) and spectro-electrochemistry results revealed that P-3 is a low band gap polymer (1.18 eV) having both p-and n-type property which is superior to the copolymers synthesized using M-1 and M-2. (C) 2010 Elsevier B. V. All rights reserved.
• A facile method to synthesize [A′(D′AD)₂]-based push–pull small molecules for organic photovoltaics
  作者：Mohamed Shaker、Jong-Hoon Lee、Cuc Kim Trinh、Wonbin Kim、Kwanghee Lee、Jae-Suk Lee

  DOI：10.1039/c5ra06660c

  日期：——

  small molecules based on the [A′(D′AD)2] architecture was developed using selective direct heteroarylation of the C–H bond with a Pd(AcO)2/Bu4NBr simple catalytic system. The C–H arylation of the unsymmetrical compound 4-(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)-7-(thiophen-2-yl)benzo[c][1,2,5] thiadiazole (5) showed that the (C5) in the ethyldioxythiophene moiety is more reactive towards C–H arylation

  利用C–H键与Pd（AcO）2 /的选择性直接杂芳基化反应，首次开发了一种有效的合成一系列基于[A'（D'AD）2 ]结构的小分子的途径。Bu 4 NBr简单催化体系。不对称化合物4-（2,3-二氢噻吩并[3,4- b ] [1,4]二恶英-5-基）-7-（噻吩-2-基）苯并[ c ] [的CH芳基化1,2,5]噻二唑（5）表明，乙基二氧噻吩部分中的（C5）比其噻吩单元中的对应物对CH芳基化反应更具活性。新的小分子带有两个不同的受体和/或供体，从而减小了电子带隙并提高了推挽系统的强度以及分子内电荷从供体转移到受体单元的数量。内酰胺和含酰亚胺的受体由于其良好的共轭结构，强大的π-π相互作用和高电子亲和力以及它们在光伏共轭材料中作为电子吸收单元的潜力而被用作第二个电子吸收单元。所有小分子均显示宽吸收光谱和光学带隙，估计在1.72–1.29 eV范围内。从循环伏安法，V oc）。EHID（EDBTT）2：PC