3-(7,8-dicyanodibenzo[b,e][1,4]dioxin-2-yl)acrylic acid | 1446888-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶英
• 英文名称: 3-(7,8-dicyanodibenzo[b,e][1,4]dioxin-2-yl)acrylic acid
• CAS: 1446888-26-1
• 化学式: C₁₇H₈N₂O₄
• 分子量: 304.262
• InChiKey: RALKSBGDLCIPIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103.34
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-(2-diethylaminoethanethiol) phthalonitrile 、 3-(7,8-dicyanodibenzo[b,e][1,4]dioxin-2-yl)acrylic acid 、 zinc diacetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 喹啉 为溶剂， 反应 12.0h， 以33%的产率得到tris {11,19,27-(1,2-diethylaminoethylthiol)-1,2(caffeic acid)phthalocyanine}Zn
  参考文献：
  名称：

  Synthesis and photophysicochemical properties of novel zinc phthalocyanines mono substituted with carboxyl containing functional groups

  摘要：

  This work reports on the synthesis and the physicochemical properties of novel unsymmetrically substituted zinc phthalocyanines (complexes 8,10 and 11) and their symmetrically substituted counterparts (complexes 9,12 and 13). The new complexes and their counterparts were successfully structurally characterized by IR, NMR, mass spectral and elemental analyses. Low fluorescence quantum yields (0.032) and lifetimes (0.91 ns) were obtained for the symmetrical ZnOTPc (complex 9) compared to the higher fluorescence quantum yields (0.15, 0.13, 0.10, 0.09 and 0.29) and lifetimes (4.4, 1.69, 1.69, 2.16 and 3.23 ns) obtained for ZnMPCPc (8), ZnTDTPc (12), ZnMCapPc (10), ZnMCafPc (11) and ZnTCPPc (13), respectively. All the complexes showed the ability to produce singlet oxygen with the highest triplet quantum yields obtained for 8 and 10(0.80 and 0.65 respectively). High triplet lifetimes (109-286 mu s) were obtained for all complexes. Complex 8 showed the longest triplet and fluorescence lifetimes as well the largest triplet state and singlet oxygen quantum yields. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.09.007
• 作为产物：
  描述：

  咖啡酸 、 4,5-二氯邻苯二甲腈 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以92%的产率得到3-(7,8-dicyanodibenzo[b,e][1,4]dioxin-2-yl)acrylic acid
  参考文献：
  名称：

  Synthesis and photophysicochemical properties of novel zinc phthalocyanines mono substituted with carboxyl containing functional groups

  摘要：

  This work reports on the synthesis and the physicochemical properties of novel unsymmetrically substituted zinc phthalocyanines (complexes 8,10 and 11) and their symmetrically substituted counterparts (complexes 9,12 and 13). The new complexes and their counterparts were successfully structurally characterized by IR, NMR, mass spectral and elemental analyses. Low fluorescence quantum yields (0.032) and lifetimes (0.91 ns) were obtained for the symmetrical ZnOTPc (complex 9) compared to the higher fluorescence quantum yields (0.15, 0.13, 0.10, 0.09 and 0.29) and lifetimes (4.4, 1.69, 1.69, 2.16 and 3.23 ns) obtained for ZnMPCPc (8), ZnTDTPc (12), ZnMCapPc (10), ZnMCafPc (11) and ZnTCPPc (13), respectively. All the complexes showed the ability to produce singlet oxygen with the highest triplet quantum yields obtained for 8 and 10(0.80 and 0.65 respectively). High triplet lifetimes (109-286 mu s) were obtained for all complexes. Complex 8 showed the longest triplet and fluorescence lifetimes as well the largest triplet state and singlet oxygen quantum yields. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2012.09.007