3,6-difluoropyromellitic acid tetramethyl ester | 10585-07-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,6-difluoropyromellitic acid tetramethyl ester
• 英文别名: 3,6-Difluormellitsaeure(IV)-tetramethylester；Tetramethyldifluoropyromellitate；tetramethyl 3,6-difluorobenzene-1,2,4,5-tetracarboxylate
• CAS: 10585-07-6
• 化学式: C₁₄H₁₂F₂O₈
• 分子量: 346.241
• InChiKey: FADQJODRAUOEEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,6-difluoropyromellitic acid tetramethyl ester 在 氢溴酸 作用下， 以 N,N-二甲基乙酰胺 、 溶剂黄146 为溶剂， 反应 40.0h， 生成 二羟基-苯-1,2,4,5-四羧酸
  参考文献：
  名称：

  Polyimide and Imide Compound Exhibiting Bright Red Fluorescence with Very Large Stokes Shifts via Excited-State Intramolecular Proton Transfer

  摘要：

  A novel polyimide (PI) emitting a prominent red fluorescence was prepared based on 3,6-dihydroxypyromellitic dianhydride (P2HDA) and 4,4'-diaminocyclohexylmethane (DCHM). In order to investigate the fluorescence properties of the PI, an imide model compound, N,N'-dicyclohexyl-3,6-dihydroxypyromellitimide (P2H-Ch), corresponding to one repeating unit of the PI, was also synthesized. The UVvis absorption and fluorescence spectra of P2H-Ch in CHCl3 and the solid PI film demonstrated intense red fluorescence at around 640 nm with a very large Stokes shift (nu) of 7655 and 8994 cm(-1), respectively, via the excited-state intramolecular proton transfer (ESIPT). Moreover, the corresponding monoanion and dianion species were formed in basic conditions with an organic base (DBU) and basic salt (NaOH), which were characterized by highly visible halochromism. The introduction of -OH groups into the pyromellitic moiety of imide compounds or PIs at their para positions led to the long-wavelength fluorescent emission as well as to the high pH sensitivity.

  DOI：

  10.1021/ma502456f
• 作为产物：
  描述：

  甲醇 、 1,4-Difluoro-2,3,5,6-benzenetetracarboxylic dianhydride 在 硫酸 作用下， 反应 48.0h， 以71%的产率得到3,6-difluoropyromellitic acid tetramethyl ester
  参考文献：
  名称：

  Polyimide and Imide Compound Exhibiting Bright Red Fluorescence with Very Large Stokes Shifts via Excited-State Intramolecular Proton Transfer

  摘要：

  A novel polyimide (PI) emitting a prominent red fluorescence was prepared based on 3,6-dihydroxypyromellitic dianhydride (P2HDA) and 4,4'-diaminocyclohexylmethane (DCHM). In order to investigate the fluorescence properties of the PI, an imide model compound, N,N'-dicyclohexyl-3,6-dihydroxypyromellitimide (P2H-Ch), corresponding to one repeating unit of the PI, was also synthesized. The UVvis absorption and fluorescence spectra of P2H-Ch in CHCl3 and the solid PI film demonstrated intense red fluorescence at around 640 nm with a very large Stokes shift (nu) of 7655 and 8994 cm(-1), respectively, via the excited-state intramolecular proton transfer (ESIPT). Moreover, the corresponding monoanion and dianion species were formed in basic conditions with an organic base (DBU) and basic salt (NaOH), which were characterized by highly visible halochromism. The introduction of -OH groups into the pyromellitic moiety of imide compounds or PIs at their para positions led to the long-wavelength fluorescent emission as well as to the high pH sensitivity.

  DOI：

  10.1021/ma502456f