4,9-bis(5-(2,5-bis(2-ethylhexyl)-3,6-dioxo-4-(thiophen-2-yl)-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl)thiophen-2-yl)-2,7-dioctylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone | 1620471-13-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,9-bis(5-(2,5-bis(2-ethylhexyl)-3,6-dioxo-4-(thiophen-2-yl)-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl)thiophen-2-yl)-2,7-dioctylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
• 英文别名: 2-[5-[2,5-Bis(2-ethylhexyl)-3,6-dioxo-1-thiophen-2-ylpyrrolo[3,4-c]pyrrol-4-yl]thiophen-2-yl]-9-[5-[2,5-bis(2-ethylhexyl)-3,6-dioxo-1-thiophen-2-ylpyrrolo[3,4-c]pyrrol-4-yl]thiophen-2-yl]-6,13-bis(2-ethylhexyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone；2-[5-[2,5-bis(2-ethylhexyl)-3,6-dioxo-1-thiophen-2-ylpyrrolo[3,4-c]pyrrol-4-yl]thiophen-2-yl]-9-[5-[2,5-bis(2-ethylhexyl)-3,6-dioxo-1-thiophen-2-ylpyrrolo[3,4-c]pyrrol-4-yl]thiophen-2-yl]-6,13-bis(2-ethylhexyl)-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 1620471-13-7
• 化学式: C₉₀H₁₁₄N₆O₈S₄
• 分子量: 1536.19
• InChiKey: WIQRAVRSEGIRAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.8
• 重原子数：
  108
• 可旋转键数：
  42
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  242
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  3-(5-溴-2-噻吩基)-2,5-双(2-乙基己基)-2,5-二氢-6-(2-噻吩基)吡咯并[3,4-C]吡咯-1,4-二酮 、 2,7-bis(2-ethylhexyl)-4,9-bis(tributylstannyl)benzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 甲苯 为溶剂， 以72%的产率得到4,9-bis(5-(2,5-bis(2-ethylhexyl)-3,6-dioxo-4-(thiophen-2-yl)-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrol-1-yl)thiophen-2-yl)-2,7-dioctylbenzo[lmn][3,8]phenanthroline-1,3,6,8(2H,7H)-tetraone
  参考文献：
  名称：

  A solution-processable electron acceptor based on diketopyrrolopyrrole and naphthalenediimide motifs for organic solar cells

  摘要：

  A novel, solution-processable small molecular electron acceptor (HP1) based on diketopyrrolopyrrole and naphthalenediimide fragments was designed and synthesized via a Stille coupling reaction, characterized by spectroscopic means, and exhibited excellent solubility and thermal stability. HP1 exerted strong and very broad absorption tailing into the near infra-red region, with appropriate energy levels matching with the archetypal electron donor, poly(3-hexylthiophene) (P3HT), and afforded 1.02% power conversion efficiency with a high open-circuit voltage (1.05 V) when tested in solution-processable bulk-heterojunction devices. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.017

文献信息

• A solution-processable electron acceptor based on diketopyrrolopyrrole and naphthalenediimide motifs for organic solar cells
  作者：Hemlata Patil、Akhil Gupta、Ante Bilic、Sidhanath V. Bhosale、Sheshanath V. Bhosale

  DOI：10.1016/j.tetlet.2014.06.017

  日期：2014.8

  A novel, solution-processable small molecular electron acceptor (HP1) based on diketopyrrolopyrrole and naphthalenediimide fragments was designed and synthesized via a Stille coupling reaction, characterized by spectroscopic means, and exhibited excellent solubility and thermal stability. HP1 exerted strong and very broad absorption tailing into the near infra-red region, with appropriate energy levels matching with the archetypal electron donor, poly(3-hexylthiophene) (P3HT), and afforded 1.02% power conversion efficiency with a high open-circuit voltage (1.05 V) when tested in solution-processable bulk-heterojunction devices. (C) 2014 Elsevier Ltd. All rights reserved.