5,5'-bis (5-bromo-3',4-didodecyl-2,2'-biselenophene-5-yl)-2,2'-biselenophene | 1356037-69-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5,5'-bis (5-bromo-3',4-didodecyl-2,2'-biselenophene-5-yl)-2,2'-biselenophene
• 英文别名: 5-Bromo-2-[5-[5-[5-[5-(5-bromo-3-dodecylselenophen-2-yl)-3-dodecylselenophen-2-yl]selenophen-2-yl]selenophen-2-yl]-4-dodecylselenophen-2-yl]-3-dodecylselenophene；5-bromo-2-[5-[5-[5-[5-(5-bromo-3-dodecylselenophen-2-yl)-3-dodecylselenophen-2-yl]selenophen-2-yl]selenophen-2-yl]-4-dodecylselenophen-2-yl]-3-dodecylselenophene
• CAS: 1356037-69-8
• 化学式: C₇₂H₁₀₈Br₂Se₆
• 分子量: 1607.22
• InChiKey: DSEIRCSQCBWIDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23.74
• 重原子数：
  80
• 可旋转键数：
  49
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  5,5'-bis (3',4-didodecyl-2,2'-biselenophene-5-yl)-2,20-bi-selenophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 1.0h， 以99%的产率得到5,5'-bis (5-bromo-3',4-didodecyl-2,2'-biselenophene-5-yl)-2,2'-biselenophene
  参考文献：
  名称：

  Synthesis and characterization of new selenophene-based conjugated polymers for organic photovoltaic cells

  摘要：

  AbstractThree new polymers poly(3,4′′′‐didodecyl) hexaselenophene) (P6S), poly(5,5′‐bis(4,4′‐didodecyl‐2,2′‐biselenophene‐5‐yl)‐2,2′‐biselenophene) (HHP6S), and poly(5,5′‐bis(3′,4‐didodecyl‐2,2′‐biselenophene‐5‐yl)‐2,2′‐biselenophene) (TTP6S) that have the same selenophene‐based polymer backbone but different side chain patterns were designed and synthesized. The weight‐averaged molecular weights (Mw) of P6S, HHP6S, and TTP6S were found to be 19,100, 24,100, and 19,700 with polydispersity indices of 2.77, 1.48, and 1.41, respectively. The UV–visible absorption maxima of P6S, HHP6S, and TTP6S are at 524, 489, and 513 nm, respectively, in solution and at 569, 517, and 606 nm, respectively, in the film state. The polymers P6S, HHP6S, and TTP6S exhibit low band gaps of 1.74, 1.95, and 1.58 eV, respectively. The field‐effect mobilities of P6S, HHP6S, and TTP6S were measured to be 1.3 × 10−4, 3.9 × 10−6, and 3.2 × 10−4 cm2 V−1 s−1, respectively. A photovoltaic device with a TTP6S/[6,6]‐phenyl C71‐butyric acid methyl ester (1:3, w/w) blend film active layer was found to exhibit an open circuit voltage (VOC) of 0.71 V, a short circuit current (JSC) of 5.72 mA cm−2, a fill factor of 0.41, and a power conversion efficiency (PCE) of 1.67% under AM 1.5 G (100 mW cm−2) illumination. TTP6S has the most planar backbone of the tested polymers, which results in strong π–π interchain interactions and strong aggregation, leading to broad absorption, high mobility, a low band gap, and the highest PCE. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

  DOI：

  10.1002/pola.25064

文献信息

• Synthesis and characterization of new selenophene-based conjugated polymers for organic photovoltaic cells
  作者：Woo-Hyung Lee、Sang Kyu Lee、Seon Kyoung Son、Ji-Eun Choi、Won Suk Shin、Kyoungkon Kim、Soo-Hyoung Lee、Sang-Jin Moon、In-Nam Kang

  DOI：10.1002/pola.25064

  日期：2012.2.1

  AbstractThree new polymers poly(3,4′′′‐didodecyl) hexaselenophene) (P6S), poly(5,5′‐bis(4,4′‐didodecyl‐2,2′‐biselenophene‐5‐yl)‐2,2′‐biselenophene) (HHP6S), and poly(5,5′‐bis(3′,4‐didodecyl‐2,2′‐biselenophene‐5‐yl)‐2,2′‐biselenophene) (TTP6S) that have the same selenophene‐based polymer backbone but different side chain patterns were designed and synthesized. The weight‐averaged molecular weights (Mw) of P6S, HHP6S, and TTP6S were found to be 19,100, 24,100, and 19,700 with polydispersity indices of 2.77, 1.48, and 1.41, respectively. The UV–visible absorption maxima of P6S, HHP6S, and TTP6S are at 524, 489, and 513 nm, respectively, in solution and at 569, 517, and 606 nm, respectively, in the film state. The polymers P6S, HHP6S, and TTP6S exhibit low band gaps of 1.74, 1.95, and 1.58 eV, respectively. The field‐effect mobilities of P6S, HHP6S, and TTP6S were measured to be 1.3 × 10−4, 3.9 × 10−6, and 3.2 × 10−4 cm2 V−1 s−1, respectively. A photovoltaic device with a TTP6S/[6,6]‐phenyl C71‐butyric acid methyl ester (1:3, w/w) blend film active layer was found to exhibit an open circuit voltage (VOC) of 0.71 V, a short circuit current (JSC) of 5.72 mA cm−2, a fill factor of 0.41, and a power conversion efficiency (PCE) of 1.67% under AM 1.5 G (100 mW cm−2) illumination. TTP6S has the most planar backbone of the tested polymers, which results in strong π–π interchain interactions and strong aggregation, leading to broad absorption, high mobility, a low band gap, and the highest PCE. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011