4-Hexyl-2-[4-(4-hexylthiophen-2-yl)phenyl]thiophene | 249575-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Hexyl-2-[4-(4-hexylthiophen-2-yl)phenyl]thiophene
• CAS: 249575-14-2
• 化学式: C₂₆H₃₄S₂
• 分子量: 410.688
• InChiKey: WJQJTDMEABNECW-UHFFFAOYSA-N

物化性质

• 熔点：
  54-57 °C(Solv: acetone (67-64-1))
• 沸点：
  523.3±45.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  4-Hexyl-2-[4-(4-hexylthiophen-2-yl)phenyl]thiophene 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以37%的产率得到1,4-bis(5-bromo-4-hexylthiophen-2-yl)benzene
  参考文献：
  名称：

  Effect of Incorporated Nitrogens on the Planarity and Photovoltaic Performance of Donor–Acceptor Copolymers

  摘要：

  Systematic control of the chemical structure of conjugated polymers is critically important to elucidate the relationship between the conjugated polymer structures and properties and to optimize their performance in bulk heterojunction (BHJ) polymer solar cell (PSC) devices. Herein, we synthesized three new copolymers, i.e., P0, P1, and P2; these copolymers contain the same benzodithiophene donor unit but have different acceptor units with different numbers of nitrogen atoms in the range of 0-2. The effects of the introduced nitrogen atoms on the structural, optical, electrical, and photovoltaic properties of the conjugated polymers were investigated; the structural properties of the polymers, in particular, were studied using both experimental (grazing-incidence X-ray scattering (GIXS) measurements) and computational methods (molecular simulation). As the number of introduced nitrogen atoms increased, the planarity of the main chain conformation increased in the order of P0 < P1 < P2 Additionally, the P0, P1, and P2 polymers showed increased interlayer domain spacings of 1.61, 1.72, and 1.78 nm, respectively, with increased intermolecular ordering. These results were in excellent agreement with the simulation results. In addition, the enhanced planarity resulted in a red-shifting at the onset of absorption in the polymer film from 544 to 585 nm, a downshift in the lowest unoccupied molecular orbital (LUMO) energy level from -3.02 to -3.26 eV, and an increase in the hole mobility from 2.33 X 10(-6) to 3.78 x 10(-5) cm(2)/(V s). As a result, we observed dramatically enhanced performance of the PSCs in the order of P0 < P1 < P2. For example, the P2:PC61BM device exhibited a 3.5-fold improvement in power conversion efficiency (PCE) compared to that of P0:PC61BM. The further optimization of P2 with PC71BM showed the PCE of 3.22%.

  DOI：

  10.1021/ma301362t
• 作为产物：
  描述：

  3-己基噻吩 、 1,4-二溴苯 在 2,2,6,6-四甲基哌啶 、 乙基氯化镁 、 [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](triphenylphosphine)nickel(II) dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以45%的产率得到4-Hexyl-2-[4-(4-hexylthiophen-2-yl)phenyl]thiophene
  参考文献：
  名称：

  NHC镍催化剂将噻吩环引入多卤代芳族化合物中的多重偶联偏好研究

  摘要：

  几种噻吩衍生物可以通过乙基氯化镁（EtMgCl）和催化量的2,2,6,6-四甲基哌啶（TMP-H）结合而去质子化。在具有NHC配体（IPr）的镍催化剂存在下，金属化的3-己基噻吩与2,3-和2,5-二溴噻吩反应，以提供二偶联产物，尽管等摩尔反应，但仅与二溴噻吩的回收一起提供。3-己基噻吩与二溴代苯衍生物的1：1反应也可得到双偶合产物作为唯一产物。

  DOI：

  10.1016/j.tetlet.2013.01.127