3,6-dibutoxy-4,5-bis([2,2'-bithiophene]-5-yl)phthalonitrile | 365218-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 3,6-dibutoxy-4,5-bis([2,2'-bithiophene]-5-yl)phthalonitrile
• 英文别名: 3,6-Dibutoxy-4,5-bis(5-thiophen-2-ylthiophen-2-yl)benzene-1,2-dicarbonitrile
• CAS: 365218-23-1
• 化学式: C₃₂H₂₈N₂O₂S₄
• 分子量: 600.851
• InChiKey: ROALUVIEIGHRTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  179
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,6-dibutoxy-4,5-bis([2,2'-bithiophene]-5-yl)phthalonitrile 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 zinc(II) chloride 作用下， 以 正己醇 为溶剂， 反应 18.0h， 以54%的产率得到[1,4,8,11,15,18,22,25-octabutoxy-2,3,9,10,16,17,23,24-octa([2,2'-bithiophene]-5-yl)phthalocyaninato]zinc(II)
  参考文献：
  名称：

  Elongation of the π-System of Phthalocyanines by Introduction of Thienyl Substituents at the Peripheral β Positions. Synthesis and Characterization

  摘要：

  1,4,8,11,15,18,22,25-Octabutoxyphthalocyanines ((OBu)(8)Pcs) having eight 2-thienyl (1) and [2,2 ' -bithiophene] -5-yl (2) groups at beta positions and their zinc(II) and cobalt(II) derivatives were prepared from 2-thienyl- (3) or [2,2 ' -bithiophenel-5-yl (4)-substituted phthalonitriles in moderate to good yields. The electronic absorption spectra of the Pes showed red-shifted Q-bands relative to P-unsubstituted (OBu)8Pcs. The longer substituent, the [2,2 ' -bithiophene]-5-yl group, is more effective than the 2-thienyl group in enlarging the a-conjugated system of the Pcs. The ring oxidation potential obtained by cyclic voltammetry shifted cathodically with increasing chain length, indicating destabilization of the HOMOs. Due to the shift of the Q-band, 2-thienyl- and [2,2 ' -bithiophene]-5-yl-substituted Pes exhibit a remarkable color change from the original green color.

  DOI：

  10.1021/jo010384r
• 作为产物：
  描述：

  2-(tri-n-butyl)stannyl-5,2'-bithiophene 、 4,5-dibromo-3,6-dibutoxyphthalonitrile 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 以87.9%的产率得到3,6-dibutoxy-4,5-bis([2,2'-bithiophene]-5-yl)phthalonitrile
  参考文献：
  名称：

  Elongation of the π-System of Phthalocyanines by Introduction of Thienyl Substituents at the Peripheral β Positions. Synthesis and Characterization

  摘要：

  1,4,8,11,15,18,22,25-Octabutoxyphthalocyanines ((OBu)(8)Pcs) having eight 2-thienyl (1) and [2,2 ' -bithiophene] -5-yl (2) groups at beta positions and their zinc(II) and cobalt(II) derivatives were prepared from 2-thienyl- (3) or [2,2 ' -bithiophenel-5-yl (4)-substituted phthalonitriles in moderate to good yields. The electronic absorption spectra of the Pes showed red-shifted Q-bands relative to P-unsubstituted (OBu)8Pcs. The longer substituent, the [2,2 ' -bithiophene]-5-yl group, is more effective than the 2-thienyl group in enlarging the a-conjugated system of the Pcs. The ring oxidation potential obtained by cyclic voltammetry shifted cathodically with increasing chain length, indicating destabilization of the HOMOs. Due to the shift of the Q-band, 2-thienyl- and [2,2 ' -bithiophene]-5-yl-substituted Pes exhibit a remarkable color change from the original green color.

  DOI：

  10.1021/jo010384r

文献信息

• Elongation of the π-System of Phthalocyanines by Introduction of Thienyl Substituents at the Peripheral <i>β</i> Positions. Synthesis and Characterization
  作者：Tsuyoshi Muto、Tetsuji Temma、Mutsumi Kimura、Kenji Hanabusa、Hirofusa Shirai

  DOI：10.1021/jo010384r

  日期：2001.9.1

  1,4,8,11,15,18,22,25-Octabutoxyphthalocyanines ((OBu)(8)Pcs) having eight 2-thienyl (1) and [2,2 ' -bithiophene] -5-yl (2) groups at beta positions and their zinc(II) and cobalt(II) derivatives were prepared from 2-thienyl- (3) or [2,2 ' -bithiophenel-5-yl (4)-substituted phthalonitriles in moderate to good yields. The electronic absorption spectra of the Pes showed red-shifted Q-bands relative to P-unsubstituted (OBu)8Pcs. The longer substituent, the [2,2 ' -bithiophene]-5-yl group, is more effective than the 2-thienyl group in enlarging the a-conjugated system of the Pcs. The ring oxidation potential obtained by cyclic voltammetry shifted cathodically with increasing chain length, indicating destabilization of the HOMOs. Due to the shift of the Q-band, 2-thienyl- and [2,2 ' -bithiophene]-5-yl-substituted Pes exhibit a remarkable color change from the original green color.