2,7-Bis(5-ethynyl-4-hexylthiophen-2-yl)anthracene-9,10-dione | 1276668-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2,7-Bis(5-ethynyl-4-hexylthiophen-2-yl)anthracene-9,10-dione
• 英文别名: 2,7-bis(5-ethynyl-4-hexylthiophen-2-yl)anthracene-9,10-dione
• CAS: 1276668-77-9
• 化学式: C₃₈H₃₆O₂S₂
• 分子量: 588.835
• InChiKey: WRITWLNUQZOZRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-dichloro-bis(tri-n-butylphosphine)platinum(II) 、 2,7-Bis(5-ethynyl-4-hexylthiophen-2-yl)anthracene-9,10-dione 在 copper(l) iodide N(C₂H₅)3 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到
  参考文献：
  名称：

  Synthesis, characterization and photovoltaic behavior of platinum acetylide polymers with electron-deficient 9,10-anthraquinone moiety

  摘要：

  A new class of soluble, solution-processable platinum(II) acetylide polymers functionalized with electron-deficient 9,10-anthraquinone spacer and their corresponding diplatinum model complexes were synthesized and characterized. The organometallic polymers exhibit good thermal stability and show low-energy broad absorption bands in the visible region. The effect of the presence of thiophene rings along the polymer chain on the optical and photovoltaic properties of these metallated materials was examined. The low-bandgap polymer with thiophene-eanthraquinonee-thiophene (donor-acceptor-donor) fragment can serve as a good electron donor for fabricating bulk heterojunction polymer solar cells by blending with a methanofullerene electron acceptor. At the same donor: acceptor blend ratio of 1: 4, the light-harvesting ability and solar cell efficiency notably increase when the anthraquinone ring is sandwiched by two thiophene units. Photoexcitation of such polymer solar cells results in a photoinduced electron transfer from the pi-conjugated metallopolymer to [6,6]-phenyl C-61-butyric acid methyl ester with power conversion efficiency up to similar to 0.35%. For safety concern, these metallopolymers were also tested for possible cytotoxicity and they do not show significant cytotoxic activity on human liver derived cells and skin keratinocytes at reasonable doses, rendering these functional materials safe to use in practical devices. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.08.044
• 作为产物：
  描述：

  2,7-二溴蒽醌 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 四(三苯基膦)钯 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 溶剂黄146 为溶剂， 反应 50.0h， 生成 2,7-Bis(5-ethynyl-4-hexylthiophen-2-yl)anthracene-9,10-dione
  参考文献：
  名称：

  Synthesis, characterization and photovoltaic behavior of platinum acetylide polymers with electron-deficient 9,10-anthraquinone moiety

  摘要：

  A new class of soluble, solution-processable platinum(II) acetylide polymers functionalized with electron-deficient 9,10-anthraquinone spacer and their corresponding diplatinum model complexes were synthesized and characterized. The organometallic polymers exhibit good thermal stability and show low-energy broad absorption bands in the visible region. The effect of the presence of thiophene rings along the polymer chain on the optical and photovoltaic properties of these metallated materials was examined. The low-bandgap polymer with thiophene-eanthraquinonee-thiophene (donor-acceptor-donor) fragment can serve as a good electron donor for fabricating bulk heterojunction polymer solar cells by blending with a methanofullerene electron acceptor. At the same donor: acceptor blend ratio of 1: 4, the light-harvesting ability and solar cell efficiency notably increase when the anthraquinone ring is sandwiched by two thiophene units. Photoexcitation of such polymer solar cells results in a photoinduced electron transfer from the pi-conjugated metallopolymer to [6,6]-phenyl C-61-butyric acid methyl ester with power conversion efficiency up to similar to 0.35%. For safety concern, these metallopolymers were also tested for possible cytotoxicity and they do not show significant cytotoxic activity on human liver derived cells and skin keratinocytes at reasonable doses, rendering these functional materials safe to use in practical devices. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.08.044

文献信息

• Synthesis, characterization and photovoltaic behavior of platinum acetylide polymers with electron-deficient 9,10-anthraquinone moiety
  作者：Li Li、Wing-Cheong Chow、Wai-Yeung Wong、Chung-Hin Chui、Raymond Siu-Ming Wong

  DOI：10.1016/j.jorganchem.2010.08.044

  日期：2011.3

  A new class of soluble, solution-processable platinum(II) acetylide polymers functionalized with electron-deficient 9,10-anthraquinone spacer and their corresponding diplatinum model complexes were synthesized and characterized. The organometallic polymers exhibit good thermal stability and show low-energy broad absorption bands in the visible region. The effect of the presence of thiophene rings along the polymer chain on the optical and photovoltaic properties of these metallated materials was examined. The low-bandgap polymer with thiophene-eanthraquinonee-thiophene (donor-acceptor-donor) fragment can serve as a good electron donor for fabricating bulk heterojunction polymer solar cells by blending with a methanofullerene electron acceptor. At the same donor: acceptor blend ratio of 1: 4, the light-harvesting ability and solar cell efficiency notably increase when the anthraquinone ring is sandwiched by two thiophene units. Photoexcitation of such polymer solar cells results in a photoinduced electron transfer from the pi-conjugated metallopolymer to [6,6]-phenyl C-61-butyric acid methyl ester with power conversion efficiency up to similar to 0.35%. For safety concern, these metallopolymers were also tested for possible cytotoxicity and they do not show significant cytotoxic activity on human liver derived cells and skin keratinocytes at reasonable doses, rendering these functional materials safe to use in practical devices. (C) 2010 Elsevier B.V. All rights reserved.