2-ethylhexyl 2,5-dibromothiophene-3-carboxylate | 1393644-33-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-ethylhexyl 2,5-dibromothiophene-3-carboxylate
• 英文别名: 2-Ethylhexyl 2,5-dibromothiophene-3-carboxylate
• CAS: 1393644-33-1
• 化学式: C₁₃H₁₈Br₂O₂S
• 分子量: 398.159
• InChiKey: VJWHUWWGESOKCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  溴代异辛烷 、 2,5-二溴-3-噻吩甲酸 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以82%的产率得到2-ethylhexyl 2,5-dibromothiophene-3-carboxylate
  参考文献：
  名称：

  Polymer solar cells fabricated with 4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b′]dithiophene and alkyl-substituted thiophene-3-carboxylate-containing conjugated polymers: Effect of alkyl side-chain in thiophene-3-carboxylate monomer on the device performance

  摘要：

  Four alkyl-substituted thiophene-3-carboxylate containing donor-acceptor (D-A) copolymers were designed, synthesized, and characterized. Thiophene-3-carboxylate was used as a weak electron acceptor unit in the copolymers to provide a deeper highest occupied molecular orbital (HOMO) level for obtaining a higher open-circuit voltage in polymer solar cells (PSCs). The resulting bulk heterojunction PSCs, made of the copolymers and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM), exhibited different short circuit currents (J(SC)s) and open-circuit voltages (V(OC)s), depending on the length of alkyl side-chain in the thiophene-3-carboxylate unit. Among all fabricated photovoltaic (PV) devices, PC2:PC71BM (1:1 wt. ratio) showed the highest efficiency with the highest Jsc of 10.5 mA/cm(2). Although PC5:PC71BM (1:1) displayed the highest V-OC of 0.93 V. the device efficiency was observed to be poor, which is due to poor nanophase segregation. This comparison shows that the side-chain of thiophene carboxylate in these copolymers plays a very important role in the device efficiency. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.polymer.2012.07.007

文献信息

• Polymer solar cells fabricated with 4,8-bis(2-ethylhexyloxy)benzo[1,2-b:4,5-b′]dithiophene and alkyl-substituted thiophene-3-carboxylate-containing conjugated polymers: Effect of alkyl side-chain in thiophene-3-carboxylate monomer on the device performance
  作者：Min Ju Cho、Jangwon Seo、Kai Luo、Kyung Hwan Kim、Dong Hoon Choi、Paras N. Prasad

  DOI：10.1016/j.polymer.2012.07.007

  日期：2012.8

  Four alkyl-substituted thiophene-3-carboxylate containing donor-acceptor (D-A) copolymers were designed, synthesized, and characterized. Thiophene-3-carboxylate was used as a weak electron acceptor unit in the copolymers to provide a deeper highest occupied molecular orbital (HOMO) level for obtaining a higher open-circuit voltage in polymer solar cells (PSCs). The resulting bulk heterojunction PSCs, made of the copolymers and [6,6]-phenyl-C71-butyric acid methyl ester (PC71BM), exhibited different short circuit currents (J(SC)s) and open-circuit voltages (V(OC)s), depending on the length of alkyl side-chain in the thiophene-3-carboxylate unit. Among all fabricated photovoltaic (PV) devices, PC2:PC71BM (1:1 wt. ratio) showed the highest efficiency with the highest Jsc of 10.5 mA/cm(2). Although PC5:PC71BM (1:1) displayed the highest V-OC of 0.93 V. the device efficiency was observed to be poor, which is due to poor nanophase segregation. This comparison shows that the side-chain of thiophene carboxylate in these copolymers plays a very important role in the device efficiency. (C) 2012 Elsevier Ltd. All rights reserved.