5,5'-bis(2-ethylhexyl)-2,2′-bithiophene | 1537197-38-8

• 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: 5,5'-bis(2-ethylhexyl)-2,2′-bithiophene
• 英文别名: 2-(2-Ethylhexyl)-5-[5-(2-ethylhexyl)thiophen-2-yl]thiophene；2-(2-ethylhexyl)-5-[5-(2-ethylhexyl)thiophen-2-yl]thiophene
• CAS: 1537197-38-8
• 化学式: C₂₄H₃₈S₂
• 分子量: 390.698
• InChiKey: LJIRTJCUUGKDKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.99
• 重原子数：
  26.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  草酰氯 、 5,5'-bis(2-ethylhexyl)-2,2′-bithiophene 在 吡啶 、 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 以47%的产率得到2,7-bis(2-ethylhexyl)benzo[1,2-b:6,5-b']dithiophene-4,5-dione
  参考文献：
  名称：

  Benzodithiophene–Thiadiazoloquinoxaline as an Acceptor for Ambipolar Copolymers with Deep LUMO Level and Distinct Linkage Pattern

  摘要：

  Two new conjugated copolymers, PBDTTQ-1 and PBDTTQ-2, with a distinct linked pattern between benzodithiophene-thiadiazoloquinoxaline (BDTTQ) as acceptor and bithiophene as donor were synthesized and characterized. The difference in the linkage between donor and acceptor exerts great influence on the optoelectronic properties of the two polymers. " The optical band gap decreases from 1.18 eV for PBDTTQ-1 to 1.03 eV for PBDTTQ-2, due to the lower LUMO energy level (-4.01 eV) of the latter. Moreover, density functional theory calculations demonstrate that the electron density is mainly confined on the acceptor unit in both HOMO and LUMO of PBDTTQ-1, while the electronic densities almost delocalize along the entire backbone of PBDTTQ-2, which facilitates the charge transport within the polymer chain. In contrast to PBDTTQ-1 missing any field-effect characteristics, PBDTTQ-2 exhibits ambipolar charge transporting behavior with mobilities of 1.2 x 10(-3) cm(2)/(V s) for holes and 6.0 x 10(-4) cm(2)/(V s) for electrons.

  DOI：

  10.1021/ma401938m
• 作为产物：
  描述：

  溴代异辛烷 、 2,2'-联二噻吩 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.42h， 以43%的产率得到5,5'-bis(2-ethylhexyl)-2,2′-bithiophene
  参考文献：
  名称：

  Benzodithiophene–Thiadiazoloquinoxaline as an Acceptor for Ambipolar Copolymers with Deep LUMO Level and Distinct Linkage Pattern

  摘要：

  Two new conjugated copolymers, PBDTTQ-1 and PBDTTQ-2, with a distinct linked pattern between benzodithiophene-thiadiazoloquinoxaline (BDTTQ) as acceptor and bithiophene as donor were synthesized and characterized. The difference in the linkage between donor and acceptor exerts great influence on the optoelectronic properties of the two polymers. " The optical band gap decreases from 1.18 eV for PBDTTQ-1 to 1.03 eV for PBDTTQ-2, due to the lower LUMO energy level (-4.01 eV) of the latter. Moreover, density functional theory calculations demonstrate that the electron density is mainly confined on the acceptor unit in both HOMO and LUMO of PBDTTQ-1, while the electronic densities almost delocalize along the entire backbone of PBDTTQ-2, which facilitates the charge transport within the polymer chain. In contrast to PBDTTQ-1 missing any field-effect characteristics, PBDTTQ-2 exhibits ambipolar charge transporting behavior with mobilities of 1.2 x 10(-3) cm(2)/(V s) for holes and 6.0 x 10(-4) cm(2)/(V s) for electrons.

  DOI：

  10.1021/ma401938m

文献信息

• Benzodithiophene–Thiadiazoloquinoxaline as an Acceptor for Ambipolar Copolymers with Deep LUMO Level and Distinct Linkage Pattern
  作者：Cunbin An、Sreenivasa Reddy Puniredd、Xin Guo、Timea Stelzig、Yanfei Zhao、Wojciech Pisula、Martin Baumgarten

  DOI：10.1021/ma401938m

  日期：2014.2.11

  Two new conjugated copolymers, PBDTTQ-1 and PBDTTQ-2, with a distinct linked pattern between benzodithiophene-thiadiazoloquinoxaline (BDTTQ) as acceptor and bithiophene as donor were synthesized and characterized. The difference in the linkage between donor and acceptor exerts great influence on the optoelectronic properties of the two polymers. " The optical band gap decreases from 1.18 eV for PBDTTQ-1 to 1.03 eV for PBDTTQ-2, due to the lower LUMO energy level (-4.01 eV) of the latter. Moreover, density functional theory calculations demonstrate that the electron density is mainly confined on the acceptor unit in both HOMO and LUMO of PBDTTQ-1, while the electronic densities almost delocalize along the entire backbone of PBDTTQ-2, which facilitates the charge transport within the polymer chain. In contrast to PBDTTQ-1 missing any field-effect characteristics, PBDTTQ-2 exhibits ambipolar charge transporting behavior with mobilities of 1.2 x 10(-3) cm(2)/(V s) for holes and 6.0 x 10(-4) cm(2)/(V s) for electrons.