2-(7-cyano-9,9-dihexylfluorenyl)-1,4-di(2-tetrahydropyranyloxymethyl)benzene | 403699-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 2-(7-cyano-9,9-dihexylfluorenyl)-1,4-di(2-tetrahydropyranyloxymethyl)benzene
• CAS: 403699-46-7
• 化学式: C₄₄H₅₇NO₄
• 分子量: 663.941
• InChiKey: GJMCWKDBAQVTIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.52
• 重原子数：
  49.0
• 可旋转键数：
  17.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  60.71
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(7-cyano-9,9-dihexylfluorenyl)-1,4-di(2-tetrahydropyranyloxymethyl)benzene 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以87%的产率得到2-(7-cyano-9,9-dihexylfluorenyl)-1,4-dihydroxymethylbenzene
  参考文献：
  名称：

  Sterically Hindered Fluorenyl-Substituted Poly(p-phenylenevinylenes) for Light-Emitting Diodes

  摘要：

  A new series of processable dihexylfluorenyl-substituted poly(p-phenylenevinylene) derivatives (DHF-PPVs) were synthesized by dehydrohalogenation-condensation polymerization (GILCH polymerization). The polymers were characterized by NMR, FT-IR, and elemental analysis and were completely soluble in common organic solvents, All of the polymers demonstrated bright blue-green emission with high photoluminescence (PL) efficiencies of 68-71% in chloroform, good thermal stability with decomposition temperatures above 322degreesC, and high glass transition temperatures in the range of 113-148degreesC. Cyclic voltammetry studies revealed that these polymers undergo both irreversible oxidation and reduction onsets around 0.9 and -1.5 V, which are attributed to the conjugated backbone. Polymer light-emitting diodes (PLEDs), fabricated with DHF-PPVs, as the emitting layer, poly(3,4-ethylenedioxythiophene) (PEDOT) doped with poly(styrenesulfonic acid) (PSS) (PEDOT:PSS), as the hole injection/ transporting layer, Ca cathodes, and indium-tin oxide (ITO) anodes, (ITO/PEDOT:PSS/DHF-PPVs/Ca), emitted blue-green emission with a maximum peak around 500 nm and a shoulder peak around 532 nm. For the poly[2-(9,9-dihexylfluorenyl)-1,4-phenylenevinylene] (DHF-PPV) device, a low turn-on voltage of 2.8 V (0.13 MV/cm), a maximum luminance of 12 000 cd/m(2) at 0.4 MV/cm, and a maximum external quantum efficiency of 0.53% were obtained, The latter was 33-37 times brighter and 1.6-2.8 times more efficient than those devices with poly[2-(7-methoxy-9,9-dihexylfluorenyl)-1,4-phenylenevinylene] (MDHF-PPV) and poly[2-(7-cyano-9,9-dihexylfluorenyl)-1,4-phenylenevinylene] (CNDHF-PPV).

  DOI：

  10.1021/ma010643e
• 作为产物：
  描述：

  9,9-二己基-2,7-二溴代芴 在 四(三苯基膦)钯 sodium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 34.0h， 生成 2-(7-cyano-9,9-dihexylfluorenyl)-1,4-di(2-tetrahydropyranyloxymethyl)benzene
  参考文献：
  名称：

  Sterically Hindered Fluorenyl-Substituted Poly(p-phenylenevinylenes) for Light-Emitting Diodes

  摘要：

  A new series of processable dihexylfluorenyl-substituted poly(p-phenylenevinylene) derivatives (DHF-PPVs) were synthesized by dehydrohalogenation-condensation polymerization (GILCH polymerization). The polymers were characterized by NMR, FT-IR, and elemental analysis and were completely soluble in common organic solvents, All of the polymers demonstrated bright blue-green emission with high photoluminescence (PL) efficiencies of 68-71% in chloroform, good thermal stability with decomposition temperatures above 322degreesC, and high glass transition temperatures in the range of 113-148degreesC. Cyclic voltammetry studies revealed that these polymers undergo both irreversible oxidation and reduction onsets around 0.9 and -1.5 V, which are attributed to the conjugated backbone. Polymer light-emitting diodes (PLEDs), fabricated with DHF-PPVs, as the emitting layer, poly(3,4-ethylenedioxythiophene) (PEDOT) doped with poly(styrenesulfonic acid) (PSS) (PEDOT:PSS), as the hole injection/ transporting layer, Ca cathodes, and indium-tin oxide (ITO) anodes, (ITO/PEDOT:PSS/DHF-PPVs/Ca), emitted blue-green emission with a maximum peak around 500 nm and a shoulder peak around 532 nm. For the poly[2-(9,9-dihexylfluorenyl)-1,4-phenylenevinylene] (DHF-PPV) device, a low turn-on voltage of 2.8 V (0.13 MV/cm), a maximum luminance of 12 000 cd/m(2) at 0.4 MV/cm, and a maximum external quantum efficiency of 0.53% were obtained, The latter was 33-37 times brighter and 1.6-2.8 times more efficient than those devices with poly[2-(7-methoxy-9,9-dihexylfluorenyl)-1,4-phenylenevinylene] (MDHF-PPV) and poly[2-(7-cyano-9,9-dihexylfluorenyl)-1,4-phenylenevinylene] (CNDHF-PPV).

  DOI：

  10.1021/ma010643e