4,7-bis(3,4'-dioctyl-2,2'-bithiophen-5-yl)-2,1,3-benzothiadiazole | 1095570-45-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 4,7-bis(3,4'-dioctyl-2,2'-bithiophen-5-yl)-2,1,3-benzothiadiazole
• 英文别名: 4,7-Bis[4-octyl-5-(4-octylthiophen-2-yl)thiophen-2-yl]-2,1,3-benzothiadiazole
• CAS: 1095570-45-8
• 化学式: C₅₄H₇₆N₂S₅
• 分子量: 913.541
• InChiKey: MBDZHPMISHRUFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.4
• 重原子数：
  61
• 可旋转键数：
  32
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  167
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4,7-bis(3,4'-dioctyl-2,2'-bithiophen-5-yl)-2,1,3-benzothiadiazole 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 以90%的产率得到
  参考文献：
  名称：

  Tuning the photovoltaic performance of BT-TPA chromophore based solution-processed solar cells through molecular design incorporating of bithiophene unit and fluorine-substitution

  摘要：

  A series of novel D-pi-A-pi-D typed organic small molecules (OSMs) have been designed and synthesized successfully for solution-processed bulk-heterojunction (BHJ) solar cells, consisting of thiophene (T) or bithiophene (TT) as a segment of pi-bridge, besides, incorporating benzothiadiazole (BT) or fluorinated benzothiadiazole (FBT) as the electron-withdrawing core (A), respectively. The photovoltaic (PV) performance was finely tuned via molecular design. A significantly increased short-circuit current density (Jsc) was observed for BDCTTMBT with narrow energy gap (E-g) due to the extended conjugation-length with TT-linkage, and a high open-circuit voltage (Voc) of 1.11 V was obtained for BDCTFBT due to the F-substitution with the lowest highest occupied molecular orbital (HOMO). Among them, a best power conversion efficiency (PCE) of 4.86% was achieved for BDCTFEBT based devices due to the double effect of TT-linkage and F-substitution. These results provide valuable information on design of novel PV materials. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.02.017
• 作为产物：
  描述：

  2,1,3-苯并噻二唑 在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 氢溴酸 、 溴 作用下， 以 氯仿 为溶剂， 生成 4,7-bis(3,4'-dioctyl-2,2'-bithiophen-5-yl)-2,1,3-benzothiadiazole
  参考文献：
  名称：

  Tuning the photovoltaic performance of BT-TPA chromophore based solution-processed solar cells through molecular design incorporating of bithiophene unit and fluorine-substitution

  摘要：

  A series of novel D-pi-A-pi-D typed organic small molecules (OSMs) have been designed and synthesized successfully for solution-processed bulk-heterojunction (BHJ) solar cells, consisting of thiophene (T) or bithiophene (TT) as a segment of pi-bridge, besides, incorporating benzothiadiazole (BT) or fluorinated benzothiadiazole (FBT) as the electron-withdrawing core (A), respectively. The photovoltaic (PV) performance was finely tuned via molecular design. A significantly increased short-circuit current density (Jsc) was observed for BDCTTMBT with narrow energy gap (E-g) due to the extended conjugation-length with TT-linkage, and a high open-circuit voltage (Voc) of 1.11 V was obtained for BDCTFBT due to the F-substitution with the lowest highest occupied molecular orbital (HOMO). Among them, a best power conversion efficiency (PCE) of 4.86% was achieved for BDCTFEBT based devices due to the double effect of TT-linkage and F-substitution. These results provide valuable information on design of novel PV materials. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2015.02.017

文献信息

• Crystalline low band-gap alternating indolocarbazole and benzothiadiazole-cored oligothiophene copolymer for organic solar cell applications
  作者：Jianping Lu、Fushun Liang、Nicolas Drolet、Jianfu Ding、Ye Tao、Raluca Movileanu

  DOI：10.1039/b811031j

  日期：——

  A low band-gap alternating copolymer of indolocarbazole and benzothiadiazole-cored oligothiophene demonstrated balanced crystallinity and solubility; a solar cell combining this polymer with PC61BM in a preliminary test demonstrated power conversion efficiencies of 3.6%.

  吲哚并咔唑与苯并噻二唑基团为核心的多噻吩低带隙交替共聚物表现出平衡的结晶性和溶解性；在初步测试中，将该聚合物与PC61BM结合用于太阳能电池，其功率转换效率达到了3.6%。