5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-2,8-di(thiophen-2-yl)-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium | 1359876-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-2,8-di(thiophen-2-yl)-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
• CAS: 1359876-91-7
• 化学式: C₂₇H₂₃BF₂N₂S₂
• 分子量: 488.433
• InChiKey: TVCRUWHXWOIUQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-2,8-di(thiophen-2-yl)-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  新型基于噻吩的BODIPY RuII矩形的自组装：对癌细胞具有选择性的潜在抗增殖剂

  摘要：

  通过新型噻吩官能化的二吡啶基BODIPY配体，BDPS和钌（II）前体的自组装，设计并合成了新型Ru（2 + 2）矩形。该复合物对癌细胞具有剂量依赖性的抗增殖活性，其中某些化合物选择性杀死癌细胞。BODIPY产生的净荧光使我们能够看到它们在癌细胞中的位置。此外，金属矩形显示出与生物分子结合的强烈倾向。

  DOI：

  10.1002/chem.201704368
• 作为产物：
  描述：

  苯甲酰氯 在 N-碘代丁二酰亚胺 、 potassium phosphate monohydrate 、 三氟化硼乙醚 、 palladium diacetate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成 5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-2,8-di(thiophen-2-yl)-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
  参考文献：
  名称：

  Geometry Relaxation-Induced Large Stokes Shift in Red-Emitting Borondipyrromethenes (BODIPY) and Applications in Fluorescent Thiol Probes

  摘要：

  2-Thienyl and 2,6-bisthienyl BODIPY derivatives (BS-SS and BS-DS) were prepared that show intense absorption (epsilon = 65000 M-1 cm(-1) at 507 nm) and a large Stokes shift (96 nm) vs the small Stokes shift of typical BODIPY (<15 nm). Control compounds with a thienyl unit at the 8-position or phenyl substituents at the 2,6-positions were prepared (BS-1 and 9). BS-1 shows absorption/emission in the blue-shifted range and a small Stokes shift (12 nm). Compound 9 shows absorption in the red-shifted range, but the Stokes shift (<30 nm) is much smaller than that for BS-SS and BS-DS. DFT calculations propose the large Stokes shifts of BS-SS and BS-DS are due to the remarkable geometry relaxation upon photoexcitation and its substantial effect on the energy levels of molecular orbitals. For the dyes with small Stokes shifts, much smaller geometry relaxations were found. The fluorophores were used for fluorescent thiol probes, with 2,4-dinitrobenzenesulfonyl (DNBS) as the fluorescence switch. Both fluorescence OFF-ON and unprecedented ON-OFF transduction were observed, which are attributed to the different photoinduced intramolecular electron-transfer (PET) profile. All the photophysics were rationalized by DFT calculations based on the concept of "electronic states" instead of the very often used approximation of "molecular orbitals".

  DOI：

  10.1021/jo202215x

文献信息

• Geometry Relaxation-Induced Large Stokes Shift in Red-Emitting Borondipyrromethenes (BODIPY) and Applications in Fluorescent Thiol Probes
  作者：Yinghui Chen、Jianzhang Zhao、Huimin Guo、Lijuan Xie

  DOI：10.1021/jo202215x

  日期：2012.3.2

  2-Thienyl and 2,6-bisthienyl BODIPY derivatives (BS-SS and BS-DS) were prepared that show intense absorption (epsilon = 65000 M-1 cm(-1) at 507 nm) and a large Stokes shift (96 nm) vs the small Stokes shift of typical BODIPY (<15 nm). Control compounds with a thienyl unit at the 8-position or phenyl substituents at the 2,6-positions were prepared (BS-1 and 9). BS-1 shows absorption/emission in the blue-shifted range and a small Stokes shift (12 nm). Compound 9 shows absorption in the red-shifted range, but the Stokes shift (<30 nm) is much smaller than that for BS-SS and BS-DS. DFT calculations propose the large Stokes shifts of BS-SS and BS-DS are due to the remarkable geometry relaxation upon photoexcitation and its substantial effect on the energy levels of molecular orbitals. For the dyes with small Stokes shifts, much smaller geometry relaxations were found. The fluorophores were used for fluorescent thiol probes, with 2,4-dinitrobenzenesulfonyl (DNBS) as the fluorescence switch. Both fluorescence OFF-ON and unprecedented ON-OFF transduction were observed, which are attributed to the different photoinduced intramolecular electron-transfer (PET) profile. All the photophysics were rationalized by DFT calculations based on the concept of "electronic states" instead of the very often used approximation of "molecular orbitals".
• Self-Assembly of Novel Thiophene-Based BODIPY Ru^II Rectangles: Potential Antiproliferative Agents Selective Against Cancer Cells
  作者：Gajendra Gupta、Abhishek Das、Sourav Panja、Ji Yeon Ryu、Junseong Lee、Nripendranath Mandal、Chang Yeon Lee

  DOI：10.1002/chem.201704368

  日期：2017.12.6

  Novel Ru (2+2) rectangles were designed and synthesized by self‐assembly of a new thiophene‐functionalized dipyridyl BODIPY ligand, BDPS, and ruthenium(II) precursors. The complexes exhibited dose‐dependent antiproliferative activities against cancer cells, in which some compounds selectively kill cancer cells. The net fluorescence due to BODIPY allowed us to visualize their location inside cancer

  通过新型噻吩官能化的二吡啶基BODIPY配体，BDPS和钌（II）前体的自组装，设计并合成了新型Ru（2 + 2）矩形。该复合物对癌细胞具有剂量依赖性的抗增殖活性，其中某些化合物选择性杀死癌细胞。BODIPY产生的净荧光使我们能够看到它们在癌细胞中的位置。此外，金属矩形显示出与生物分子结合的强烈倾向。