3,4-二氰基苯甲酰基氯化物 | 437552-35-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3,4-二氰基苯甲酰基氯化物
• 中文别名: 1-丙酮,2-氨基-1-(2-甲氧苯基)-
• 英文名称: 3,4-dicyanobezoyl chloride
• 英文别名: 3,4-Dicyanobenzoyl chloride
• CAS: 437552-35-7
• 化学式: C₉H₃ClN₂O
• 分子量: 190.589
• InChiKey: FUQQNZDXUMWAJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甘氨酸乙酯盐酸盐 、 3,4-二氰基苯甲酰基氯化物 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以78%的产率得到4-carbonyl(N-glycine ethyl ester)phthalonitrile
  参考文献：
  名称：

  Modified Phthalocyanines for Efficient Near-IR Sensitization of Nanostructured TiO₂ Electrode

  摘要：

  A zinc phthalocyanine with tyrosine substituents (ZnPcTyr), modified for efficient far-red/near-IR performance in dye-sensitized nanostructured TiO2 solar cells, and its reference, glycine-substituted zinc phthalocyanine, (ZnPcGly), were synthesized and characterized. The compounds were studied spectroscopically, electrochemically, and photoelectrochemically. Incorporating tyrosine groups into phthalocyanine makes the dye ethanol-soluble and reduces surface aggregation as a result of steric effects. The performance of a solar cell based on ZnPcTyr is much better than that based on ZnPcGly. Addition of 3alpha,7alpha-dihydroxy-5beta-cholic acid (cheno) and 4-tert-butylpyridine (TBP) to the dye solution when preparing a dye-sensitized TiO2 electrode diminishes significantly the surface aggregation and, therefore, improves the performance of solar cells based on these phthalocyanines. The highest monochromatic incident photo-to-current conversion efficiency (IPCE) of similar to24% at 690 nm and an overall conversion efficiency (eta) of 0.54% were achieved for a cell based on a ZnPcTyr-sensitized TiO2 electrode. Addition of TBP in the electrolyte decreases the IPCE and eta considerably, although it increases the open-circuit photovoltage. Time-resolved transient absorption measurements of interfacial electron-transfer kinetics in a ZnPoTyr-sensitized nanostructured 702 thin film show that electron injection from the excited state of the dye into the conduction band of TiO2 is completed in similar to500 fs and that more than half of the injected electrons recombines with the oxidized dye molecules in similar to300 ps. In addition to surface aggregation, the very fast electron recombination is most likely responsible for the low performance of the solar cell based on ZnPcTyr.

  DOI：

  10.1021/ja0178012
• 作为产物：
  描述：

  3,4-二溴苯甲醛 在 sodium chlorite 、 sodium dihydrogenphosphate 、 氯化亚砜 、 双氧水 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 28.0h， 生成 3,4-二氰基苯甲酰基氯化物
  参考文献：
  名称：

  Synthesis and Characterization of Peripherally Ferrocene-modified Zinc Phthalocyanine for Dye-sensitized Solar Cell

  摘要：

  为了在染料敏化纳米结构 $TiO_2$ 太阳能电池中实现高效的远红外/近红外性能，我们合成了外围二茂铁取代的酞菁锌（ZnPc-Fc）并对其进行了结构表征。在酞菁中掺入二茂铁可以极大地提高染料在极性有机溶剂中的溶解度，并减少由于大块二茂铁取代基的立体效应而导致的表面聚集。ZnPc-Fc 中二茂铁和酞菁之间的电子转移反应途径从 S1 状态的荧光完全熄灭（< 0.08% vs ZnPc）得到了证明。ZnPc-Fc 在二甲基亚砜（DMSO）中的瞬态吸收光谱在 542 和 682 纳米波长处观察到强烈的吸收带。此外，在 450 - 600 nm 和 750 - 850 nm 处出现的激发态吸收信号是由于酞菁阴离子形成了电荷分离态。经测定，ZnPc-Fc 中电荷分离态的寿命为 $170{\pm}8$ ps，比 ZnPc 短近 17 倍。

  DOI：

  10.5012/bkcs.2010.31.11.3272

文献信息

• Phthalocyanine dyes and their preparation and use
  申请人：Baettig Kurt

  公开号：US20090155177A1

  公开（公告）日：2009-06-18

  Phthalocyanine dyes of general formula (II) and, in particular, of general formula (III) wherein R 1 -R 8 , R 9 -R 12 , Me, M, m, n, o and p are as described in the specification, are excellent photosensitizers for the preparation of pharmaceutical compositions for photodynamic therapy or photo diagnostics.

  通式（II）和特别是通式（III）的酞菁染料，在其中R1-R8，R9-R12，Me，M，m，n，o和p如说明书中所述，是制备用于光动力疗法或光诊断的药物组合物的优秀光敏剂。
• US7632345B2
  申请人：——

  公开号：US7632345B2

  公开（公告）日：2009-12-15
• US7842801B2
  申请人：——

  公开号：US7842801B2

  公开（公告）日：2010-11-30
• Modified Phthalocyanines for Efficient Near-IR Sensitization of Nanostructured TiO₂ Electrode
  作者：Jianjun He、Gábor Benkö、Ferenc Korodi、Tomás Polívka、Reiner Lomoth、Björn Åkermark、Licheng Sun、Anders Hagfeldt、Villy Sundström

  DOI：10.1021/ja0178012

  日期：2002.5.1

  A zinc phthalocyanine with tyrosine substituents (ZnPcTyr), modified for efficient far-red/near-IR performance in dye-sensitized nanostructured TiO2 solar cells, and its reference, glycine-substituted zinc phthalocyanine, (ZnPcGly), were synthesized and characterized. The compounds were studied spectroscopically, electrochemically, and photoelectrochemically. Incorporating tyrosine groups into phthalocyanine makes the dye ethanol-soluble and reduces surface aggregation as a result of steric effects. The performance of a solar cell based on ZnPcTyr is much better than that based on ZnPcGly. Addition of 3alpha,7alpha-dihydroxy-5beta-cholic acid (cheno) and 4-tert-butylpyridine (TBP) to the dye solution when preparing a dye-sensitized TiO2 electrode diminishes significantly the surface aggregation and, therefore, improves the performance of solar cells based on these phthalocyanines. The highest monochromatic incident photo-to-current conversion efficiency (IPCE) of similar to24% at 690 nm and an overall conversion efficiency (eta) of 0.54% were achieved for a cell based on a ZnPcTyr-sensitized TiO2 electrode. Addition of TBP in the electrolyte decreases the IPCE and eta considerably, although it increases the open-circuit photovoltage. Time-resolved transient absorption measurements of interfacial electron-transfer kinetics in a ZnPoTyr-sensitized nanostructured 702 thin film show that electron injection from the excited state of the dye into the conduction band of TiO2 is completed in similar to500 fs and that more than half of the injected electrons recombines with the oxidized dye molecules in similar to300 ps. In addition to surface aggregation, the very fast electron recombination is most likely responsible for the low performance of the solar cell based on ZnPcTyr.
• Synthesis and Characterization of Peripherally Ferrocene-modified Zinc Phthalocyanine for Dye-sensitized Solar Cell
  作者：Min-Shi An、Soon-Wha Kim、Jong-Dal Hong

  DOI：10.5012/bkcs.2010.31.11.3272

  日期：2010.11.20

  Synthesis and structural characterization of peripherally ferrocene-substituted zinc phthalocyanine (ZnPc-Fc) were carried out for efficient far-red/near-IR performance in dye-sensitized nanostructured $TiO_2$ solar cells. Incorporating ferrocene into phthalocyanine strongly improved the dye solubility in polar organic solvents, and reduced surface aggregation due to the steric effect of bulky ferrocene substituents. The involvement of electron transfer reaction pathways between ferrocene and phthalocyanine in ZnPc-Fc was evidenced by completely quenched fluorescence from S1 state (< 0.08% vs ZnPc). Strong absorption bands at 542 and 682 nm were observed in the transient absorption spectroscopy of ZnPc-Fc in DMSO, which was excited at a 670 nm laser pulse with a 15 ps full width at half maximum. Also, the excited state absorption signals at 450 - 600 and 750 - 850 nm appeared from the formation of charge separated state of phthalocyanine's anion. The lifetime of the charge separate state in ZnPc-Fc was determined to be $170\pm}8$ ps, which was almost 17 times shorter than that of the ZnPc.

  为了在染料敏化纳米结构 $TiO_2$ 太阳能电池中实现高效的远红外/近红外性能，我们合成了外围二茂铁取代的酞菁锌（ZnPc-Fc）并对其进行了结构表征。在酞菁中掺入二茂铁可以极大地提高染料在极性有机溶剂中的溶解度，并减少由于大块二茂铁取代基的立体效应而导致的表面聚集。ZnPc-Fc 中二茂铁和酞菁之间的电子转移反应途径从 S1 状态的荧光完全熄灭（< 0.08% vs ZnPc）得到了证明。ZnPc-Fc 在二甲基亚砜（DMSO）中的瞬态吸收光谱在 542 和 682 纳米波长处观察到强烈的吸收带。此外，在 450 - 600 nm 和 750 - 850 nm 处出现的激发态吸收信号是由于酞菁阴离子形成了电荷分离态。经测定，ZnPc-Fc 中电荷分离态的寿命为 $170\pm}8$ ps，比 ZnPc 短近 17 倍。