5-bromo-5'-(cyclohexylethynyl)-2,2'-bithiophene | 1418113-15-1

• 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-bromo-5'-(cyclohexylethynyl)-2,2'-bithiophene
• 英文别名: 2-Bromo-5-[5-(2-cyclohexylethynyl)thiophen-2-yl]thiophene；2-bromo-5-[5-(2-cyclohexylethynyl)thiophen-2-yl]thiophene
• CAS: 1418113-15-1
• 化学式: C₁₆H₁₅BrS₂
• 分子量: 351.331
• InChiKey: BUCVQYNDPBZYKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-5'-(cyclohexylethynyl)-2,2'-bithiophene 在 2,2'-联吡啶 、 bis(1,5-cyclooctadiene)nickel (0) 、 1,5-环辛二烯 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.0h， 以55.5%的产率得到bis(cyclohexylethynyl)quaterthiophene
  参考文献：
  名称：

  Molecular aggregation–performance relationship in the design of novel cyclohexylethynyl end-capped quaterthiophenes for solution-processed organic transistors

  摘要：

  The synthesis and characterization of cyclohexylethenyl end-capped quaterthiophenes is reported. Additionally, an investigation of the performance of organic field-effect transistors based on these quaterthiophenes in view of the relationship between the solid-state (or aggregate) order and the electronic performance is described. UV-vis absorption measurements revealed that the quaterthiophene with an asymmetrically substituted cyclohexylethynyl end-group induced the formation of H-type aggregates, whereas the quaterthiophene with a symmetrically substituted cyclohexylethynyl end-groups favored the formation of J-type aggregates. Two-dimensional grazing-incidence wide-angle X-ray scattering studies were performed to support the molecular structure-dependent packing of films of the new quaterthiophenes. Solution-processed quaterthiophenes were tested as the active layers of p-type organic field-effect transistors with a bottom gate/top contact geometry. The field-effect mobility of devices that incorporated asymmetric quaterthiophene molecules was quite high, exceeding 0.02 cm(2)/V s, due to H-aggregation and good in-plane ordering. In contrast, the field-effect mobility of devices that incorporated symmetrical quaterthiophenes, was low, above 5 x 10(-4) cm(2)/(V s), due to the formation of J-aggregates and poor in-plane ordering. A comparison of the symmetrical and asymmetrical quaterthiophene derivatives revealed that the molecular aggregation-dependent packing, determined by the cyclohexylethynyl end groups, was responsible for influencing the organic field-effect transistor performance. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.11.018
• 作为产物：
  描述：

  5,5'-二溴-2,2'-联噻吩 、 环己基乙炔 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 copper(l) iodide 、 二异丙胺 作用下， 反应 16.33h， 以34%的产率得到5-bromo-5'-(cyclohexylethynyl)-2,2'-bithiophene
  参考文献：
  名称：

  Molecular aggregation–performance relationship in the design of novel cyclohexylethynyl end-capped quaterthiophenes for solution-processed organic transistors

  摘要：

  The synthesis and characterization of cyclohexylethenyl end-capped quaterthiophenes is reported. Additionally, an investigation of the performance of organic field-effect transistors based on these quaterthiophenes in view of the relationship between the solid-state (or aggregate) order and the electronic performance is described. UV-vis absorption measurements revealed that the quaterthiophene with an asymmetrically substituted cyclohexylethynyl end-group induced the formation of H-type aggregates, whereas the quaterthiophene with a symmetrically substituted cyclohexylethynyl end-groups favored the formation of J-type aggregates. Two-dimensional grazing-incidence wide-angle X-ray scattering studies were performed to support the molecular structure-dependent packing of films of the new quaterthiophenes. Solution-processed quaterthiophenes were tested as the active layers of p-type organic field-effect transistors with a bottom gate/top contact geometry. The field-effect mobility of devices that incorporated asymmetric quaterthiophene molecules was quite high, exceeding 0.02 cm(2)/V s, due to H-aggregation and good in-plane ordering. In contrast, the field-effect mobility of devices that incorporated symmetrical quaterthiophenes, was low, above 5 x 10(-4) cm(2)/(V s), due to the formation of J-aggregates and poor in-plane ordering. A comparison of the symmetrical and asymmetrical quaterthiophene derivatives revealed that the molecular aggregation-dependent packing, determined by the cyclohexylethynyl end groups, was responsible for influencing the organic field-effect transistor performance. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2012.11.018

文献信息

• Molecular aggregation–performance relationship in the design of novel cyclohexylethynyl end-capped quaterthiophenes for solution-processed organic transistors
  作者：Tae Kyu An、Seung-Hoon Hahn、Sooji Nam、Hyojung Cha、Yecheol Rho、Dae Sung Chung、Moonhor Ree、Moon Seong Kang、Soon-Ki Kwon、Yun-Hi Kim、Chan Eon Park

  DOI：10.1016/j.dyepig.2012.11.018

  日期：2013.3

  The synthesis and characterization of cyclohexylethenyl end-capped quaterthiophenes is reported. Additionally, an investigation of the performance of organic field-effect transistors based on these quaterthiophenes in view of the relationship between the solid-state (or aggregate) order and the electronic performance is described. UV-vis absorption measurements revealed that the quaterthiophene with an asymmetrically substituted cyclohexylethynyl end-group induced the formation of H-type aggregates, whereas the quaterthiophene with a symmetrically substituted cyclohexylethynyl end-groups favored the formation of J-type aggregates. Two-dimensional grazing-incidence wide-angle X-ray scattering studies were performed to support the molecular structure-dependent packing of films of the new quaterthiophenes. Solution-processed quaterthiophenes were tested as the active layers of p-type organic field-effect transistors with a bottom gate/top contact geometry. The field-effect mobility of devices that incorporated asymmetric quaterthiophene molecules was quite high, exceeding 0.02 cm(2)/V s, due to H-aggregation and good in-plane ordering. In contrast, the field-effect mobility of devices that incorporated symmetrical quaterthiophenes, was low, above 5 x 10(-4) cm(2)/(V s), due to the formation of J-aggregates and poor in-plane ordering. A comparison of the symmetrical and asymmetrical quaterthiophene derivatives revealed that the molecular aggregation-dependent packing, determined by the cyclohexylethynyl end groups, was responsible for influencing the organic field-effect transistor performance. (C) 2012 Elsevier Ltd. All rights reserved.