5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-8-(thiophen-2-yl)-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium | 1359877-49-8

• 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-8-(thiophen-2-yl)-5H-5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-4-ium
• CAS: 1359877-49-8
• 化学式: C₂₃H₂₁BF₂N₂S
• 分子量: 406.307
• InChiKey: XKCFFQNGLLOFCF-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

• 作为产物：
  描述：

  5-phenyl-1,3,7,9-tetramethyldipyrrin 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 9.0h， 生成 5,5-difluoro-1,3,7,9-tetramethyl-10-phenyl-8-(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

• Light-Harvesting Fullerene Dyads as Organic Triplet Photosensitizers for Triplet–Triplet Annihilation Upconversions
  作者：Wanhua Wu、Jianzhang Zhao、Jifu Sun、Song Guo

  DOI：10.1021/jo300613g

  日期：2012.6.15

  localization of the triplet excited state on C60 were confirmed by steady-state and time-resolved spectroscopy as well as DFT calculations. The dyads were used as triplet photosensitizers for TTA upconversion, and an upconversion quantum yield up to 7.0% was observed. We propose that C60–organic chromophore dyads can be used as a general molecular structural motif for organic triplet photosensitizers, which can

  可见光捕集的C 60 –身体二联体被设计为用于三重态-三重态an灭（TTA）上转换的通用有机三重态光敏剂。使用二元组中的天线来收集激发能，然后通过从天线到C 60单元的分子内能量转移来填充C 60的单重激发态。又与C的固有系间窜越（ISC）60，将C的三重激发态的60会产生。因此，在没有任何重原子的情况下，在光激发下会形成有机二重体的三重态激发态。与C 60不同的是，二元组对515 nm的可见光有很强的吸收（C-1，ε= 70400 M –1 cm –1）或590 nm（C-2，ε= 82500 M –1 cm –1）。通过稳态和时间分辨光谱以及DFT计算，证实了从身体部分到C 60单元的有效分子内能量转移以及三重激发态在C 60上的定位。所述二元组用作TTA上转换的三重态光敏剂，并且观察到高达7.0％的上转换量子产率。我们提出，C 60 –有机发色团可被用作有机三重态光敏剂的一般分子结构
• 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".