5,5-difluoro-10-(5-(4-hydroxyphenyl)thiophen-2-yl)-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium | 1359876-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,5-difluoro-10-(5-(4-hydroxyphenyl)thiophen-2-yl)-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
• CAS: 1359876-87-1
• 化学式: C₂₃H₂₁BF₂N₂OS
• 分子量: 422.306
• InChiKey: AHLMKBJLAPKNQX-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：

  2,4-二硝基苯磺酰氯 、 5,5-difluoro-10-(5-(4-hydroxyphenyl)thiophen-2-yl)-1,3,7,9-tetramethyl-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以50%的产率得到
  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
• 作为产物：
  描述：

  在 三氟化硼乙醚 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以235.6 mg的产率得到5,5-difluoro-10-(5-(4-hydroxyphenyl)thiophen-2-yl)-1,3,7,9-tetramethyl-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".