2,3-bis(2-ethylhexyl)-5,8-di(thiophen-2-yl)quinoxaline | 1203451-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2,3-bis(2-ethylhexyl)-5,8-di(thiophen-2-yl)quinoxaline
• CAS: 1203451-20-0
• 化学式: C₃₂H₄₂N₂S₂
• 分子量: 518.831
• InChiKey: QXGVMDBBYOBMNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  36.0
• 可旋转键数：
  14.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,3-bis(2-ethylhexyl)-5,8-di(thiophen-2-yl)quinoxaline 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以95%的产率得到5,8-bis(5-bromothiophen-2-yl)-2,3-bis(2-ethylhexyl)quinoxaline
  参考文献：
  名称：

  Synthesis and Characterization of Bridged Bithiophene-Based Conjugated Polymers for Photovoltaic Applications: Acceptor Strength and Ternary Blends

  摘要：

  Six of three-component donor-acceptor random copolymers P1-P6, symbolized as (thiophene donor)(m)-(thiophene acceptor)(n), were rationally designed and successfully synthesized by the palladium-catalyzed Stille Coupling, The 4H-cyclopenta[2, 1-b:3,4-b']dithiophene (CPDT) unit serves as the donor for P1-P4, while file benzothiadiazole (BT), quinoxaline (QU), dithienoquinoxaline, and thienopyrazine (TP) units are used as the acceptor for P1, P2, P3, and P4, respectively. P5 and P6 are structurally analogous to P1 and P2 except for using the dithieno[3.2-b:2',3'-d]silole (DTS) unit as the donor. Because the band gap lowering ability of the acceptor units in the polymer is in the order TP > BR > QU presumably due to the quinoid form Population in the polymers, the optical band gaps call be well adjusted to be 1.2, 1.6, and 1.8 eV for P4, P1, and P2, respectively. It is found that file two bridged bithiophene units, CPDT and DTS, have similar steric and electronic effects oil the P1 and P5 as well as P2 and P6, respectively, leading to comparable intrinsic properties and device performances. Bulk heterojunction photovoltaic cells based oil ITO/PEDOT:PSS/polymer:PC71BM/Ca/Al configuration were fabricated and characterized. Although P4 exhibits the lowest optical band gap, broadest absorption spectrum, and highest mobility, the too low-lying LUMO level hinders the efficient exciton dissociation, resulting in a low PCE of 0.7%. Compared with poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene)-alt-4,7-(2,1,3-benzothiadiazole)] (PCPDTBT), random copolymer P1 shows more blue-shifted, broader absorption spectrum, comparable mobility, and a higher PCE of 2.0%. In view of the fact that P1 shows it higher band gap with strong absorption in visible region, while PCPDTBT-has a lower band gap to mainly absorb NIR light, a BHJ device with the active layer containing ternary blend of PCPDTBT/P-1/PC71BM was investigated and achieved an enhanced PCE of 2.5%, which outperforms the devices based on the binary blending systems of PCPDTBT/PC7, BM (PCE = 1.4%) or P1/PC71 BM (PCE = 2.0%,,) Linder the identical conditions. Such an improvement is ascribed to file complementary absorption and compatible structure of P1 and PCPDTBT polymers.

  DOI：

  10.1021/ma902206u
• 作为产物：
  描述：

  溴代异辛烷 在 magnesium 、 溶剂黄146 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 2,3-bis(2-ethylhexyl)-5,8-di(thiophen-2-yl)quinoxaline
  参考文献：
  名称：

  Synthesis and Characterization of Bridged Bithiophene-Based Conjugated Polymers for Photovoltaic Applications: Acceptor Strength and Ternary Blends

  摘要：

  Six of three-component donor-acceptor random copolymers P1-P6, symbolized as (thiophene donor)(m)-(thiophene acceptor)(n), were rationally designed and successfully synthesized by the palladium-catalyzed Stille Coupling, The 4H-cyclopenta[2, 1-b:3,4-b']dithiophene (CPDT) unit serves as the donor for P1-P4, while file benzothiadiazole (BT), quinoxaline (QU), dithienoquinoxaline, and thienopyrazine (TP) units are used as the acceptor for P1, P2, P3, and P4, respectively. P5 and P6 are structurally analogous to P1 and P2 except for using the dithieno[3.2-b:2',3'-d]silole (DTS) unit as the donor. Because the band gap lowering ability of the acceptor units in the polymer is in the order TP > BR > QU presumably due to the quinoid form Population in the polymers, the optical band gaps call be well adjusted to be 1.2, 1.6, and 1.8 eV for P4, P1, and P2, respectively. It is found that file two bridged bithiophene units, CPDT and DTS, have similar steric and electronic effects oil the P1 and P5 as well as P2 and P6, respectively, leading to comparable intrinsic properties and device performances. Bulk heterojunction photovoltaic cells based oil ITO/PEDOT:PSS/polymer:PC71BM/Ca/Al configuration were fabricated and characterized. Although P4 exhibits the lowest optical band gap, broadest absorption spectrum, and highest mobility, the too low-lying LUMO level hinders the efficient exciton dissociation, resulting in a low PCE of 0.7%. Compared with poly[2,6-(4,4-bis(2-ethylhexyl)-4H-cyclopenta[2,1-b;3,4-b']dithiophene)-alt-4,7-(2,1,3-benzothiadiazole)] (PCPDTBT), random copolymer P1 shows more blue-shifted, broader absorption spectrum, comparable mobility, and a higher PCE of 2.0%. In view of the fact that P1 shows it higher band gap with strong absorption in visible region, while PCPDTBT-has a lower band gap to mainly absorb NIR light, a BHJ device with the active layer containing ternary blend of PCPDTBT/P-1/PC71BM was investigated and achieved an enhanced PCE of 2.5%, which outperforms the devices based on the binary blending systems of PCPDTBT/PC7, BM (PCE = 1.4%) or P1/PC71 BM (PCE = 2.0%,,) Linder the identical conditions. Such an improvement is ascribed to file complementary absorption and compatible structure of P1 and PCPDTBT polymers.

  DOI：

  10.1021/ma902206u