2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-3,6-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione | 1459141-11-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-3,6-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
• 英文别名: 2,5-Bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-1,4-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrrolo[3,4-c]pyrrole-3,6-dione；2,5-bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-1,4-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrrolo[3,4-c]pyrrole-3,6-dione
• CAS: 1459141-11-7
• 化学式: C₄₄H₆₂B₂N₂O₁₂
• 分子量: 832.604
• InChiKey: VSKZYJAITLJPHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  60
• 可旋转键数：
  22
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-(bis(pyridin-2-ylmethyl)amino)-N-(4-bromophenyl)acetamide 、 2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-3,6-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 tri-tert-butylphosphonium tetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以50%的产率得到N,N'-(4',4''-(2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)bis(biphenyl-4',4-diyl))bis(2-(bis(pyridin-2-ylmethyl)amino)acetamide)
  参考文献：
  名称：

  New diketopyrrolopyrrole (DPP) derivative as fluorescent probe for Zn2+

  摘要：

  New turn-on fluorescent probe DPPL2, was rationally designed and synthesized based on the skeleton of diketopyrrolopyrrole (DPP), which presented sensitivity, selectivity for Zn2+ over other metal ions except some disturbance with Cd2+. Particularly, results demonstrated fluorescence enhancement and blue shift of DPPL2 upon Zn2+ binding. This phenomenon was a typical photoinduced electron transfer (PET) and intramolecular charge transfer (ICT) process which was attributed to diminishing the electron of the nitrogen lone pair delocalization on the DPP core upon Zn2+ binding. For comparison, DPPL3 (acylation of nitrogen atom of DPPL2) was synthesized and no fluorescence enhancement was observed, which further indicated that lone pair electrons of nitrogen atoms attached to DPP core were ascribed to PET process. H-1 NMR titrations and DFT calculations also proved that PET and ICT process of system. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.06.027
• 作为产物：
  描述：

  2-(2-(2-methoxyethoxy)ethoxy)ethyl 2-chloroacetate 、 3,6-bis(4-bromophenyl)-2,5-dihydropyrrolo[3, 4-c]pyrrole-1,4-dione 在 PdCl2(AsPh3)2 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-3,6-bis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione
  参考文献：
  名称：

  New diketopyrrolopyrrole (DPP) derivative as fluorescent probe for Zn2+

  摘要：

  New turn-on fluorescent probe DPPL2, was rationally designed and synthesized based on the skeleton of diketopyrrolopyrrole (DPP), which presented sensitivity, selectivity for Zn2+ over other metal ions except some disturbance with Cd2+. Particularly, results demonstrated fluorescence enhancement and blue shift of DPPL2 upon Zn2+ binding. This phenomenon was a typical photoinduced electron transfer (PET) and intramolecular charge transfer (ICT) process which was attributed to diminishing the electron of the nitrogen lone pair delocalization on the DPP core upon Zn2+ binding. For comparison, DPPL3 (acylation of nitrogen atom of DPPL2) was synthesized and no fluorescence enhancement was observed, which further indicated that lone pair electrons of nitrogen atoms attached to DPP core were ascribed to PET process. H-1 NMR titrations and DFT calculations also proved that PET and ICT process of system. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2013.06.027

文献信息

• New diketopyrrolopyrrole (DPP) derivative as fluorescent probe for Zn2+
  作者：Guanjun Zhang、Shiming Bi、Longfeng Song、Feng Wang、Jianjun Yu、Limin Wang

  DOI：10.1016/j.dyepig.2013.06.027

  日期：2013.12

  New turn-on fluorescent probe DPPL2, was rationally designed and synthesized based on the skeleton of diketopyrrolopyrrole (DPP), which presented sensitivity, selectivity for Zn2+ over other metal ions except some disturbance with Cd2+. Particularly, results demonstrated fluorescence enhancement and blue shift of DPPL2 upon Zn2+ binding. This phenomenon was a typical photoinduced electron transfer (PET) and intramolecular charge transfer (ICT) process which was attributed to diminishing the electron of the nitrogen lone pair delocalization on the DPP core upon Zn2+ binding. For comparison, DPPL3 (acylation of nitrogen atom of DPPL2) was synthesized and no fluorescence enhancement was observed, which further indicated that lone pair electrons of nitrogen atoms attached to DPP core were ascribed to PET process. H-1 NMR titrations and DFT calculations also proved that PET and ICT process of system. (C) 2013 Elsevier Ltd. All rights reserved.