2,2'-{5,5'-[5,5'-(selenophene-2,5-diyl)bis(3,4-dibutylthien-5,2-diyl)]bis-(selenophene-5,2-diyl)}bis(methan-1-yl-1-ylidene)dimalononitrile | 1338368-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硒吩
• 英文名称: 2,2'-{5,5'-[5,5'-(selenophene-2,5-diyl)bis(3,4-dibutylthien-5,2-diyl)]bis-(selenophene-5,2-diyl)}bis(methan-1-yl-1-ylidene)dimalononitrile
• 英文别名: 2-[[5-[3,4-Dibutyl-5-[5-[3,4-dibutyl-5-[5-(2,2-dicyanoethenyl)selenophen-2-yl]thiophen-2-yl]selenophen-2-yl]thiophen-2-yl]selenophen-2-yl]methylidene]propanedinitrile；2-[[5-[3,4-dibutyl-5-[5-[3,4-dibutyl-5-[5-(2,2-dicyanoethenyl)selenophen-2-yl]thiophen-2-yl]selenophen-2-yl]thiophen-2-yl]selenophen-2-yl]methylidene]propanedinitrile
• CAS: 1338368-14-1
• 化学式: C₄₄H₄₄N₄S₂Se₃
• 分子量: 929.872
• InChiKey: KDXAVIZUZKIBKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.96
• 重原子数：
  53
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,4-二丁基噻吩 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 正丁基锂 、 mercury(II) acetate 、 tri tert-butylphosphoniumtetrafluoroborate 、 β-丙氨酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 、 水 、 1,2-二氯乙烷 为溶剂， 反应 74.5h， 生成 2,2'-{5,5'-[5,5'-(selenophene-2,5-diyl)bis(3,4-dibutylthien-5,2-diyl)]bis-(selenophene-5,2-diyl)}bis(methan-1-yl-1-ylidene)dimalononitrile
  参考文献：
  名称：

  Dicyanovinylene-Substituted Selenophene–Thiophene Co-oligomers for Small-Molecule Organic Solar Cells

  摘要：

  We report on the design, synthesis, and characterization of a series of terminal dicyanovinylene-substituted quinquechalcogenophenes as light-harvesting small-molecule donor materials for organic solar cells. The spectroscopic, electrochemical, and thermal properties of these pentamers were investigated. The replacement of thiophene unit(s) by selenophene(s) results in a bathochromic shift of the longest wavelength absorption band with concomitant increase of the molar extinction coefficient. Cyclic voltammetry measurements revealed fully reversible oxidation and irreversible reduction processes. The highest occupied and lowest unoccupied molecular orbital (HOMO/LUMO) energy levels were determined from electrochemical measurements and lie in the range of -5.6 and -3.8 eV. Vacuum-deposited bulk-heterojunction solar cells fabricated with the novel chalcogenophenes as donor and C-60 as acceptor displayed high open-circuit voltages of up to 1 V, short-circuit currents close to 8 mA.cm(-2), and power conversion efficiencies over 3%.

  DOI：

  10.1021/cm201392c