8-[4-[2-(2-Ethoxyethoxy)ethoxy]phenyl]-2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene | 1618679-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 8-[4-[2-(2-Ethoxyethoxy)ethoxy]phenyl]-2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• 英文别名: 8-[4-[2-(2-ethoxyethoxy)ethoxy]phenyl]-2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 1618679-20-1
• 化学式: C₂₅H₃₁BF₂N₂O₃
• 分子量: 456.341
• InChiKey: VLJNXKZUACUZDJ-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：

  2-(2-(2-ethoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate 在 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.5h， 生成 8-[4-[2-(2-Ethoxyethoxy)ethoxy]phenyl]-2,2-difluoro-4,6,10,12-tetramethyl-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
  参考文献：
  名称：

  Design and synthesis of fluorescent BODIPY derivatives with D-A structure for cancer cell imaging

  摘要：

  Boron-dipyrromethene (BODIPY) as a traditional fluorescent dye has received increasing attention because of its high molar extinction coefficient, easy modification, and good light stability. In this work, three BODIPY compounds (BDP-1, BDP-2 and BDP-3) were designed and synthesized by introducing PEG chains and a naphthalimide (NI) group onto the parent structure of BODIPY. Due to the electron-withdrawing properties of NI, the compounds of BDP-2 and BDP-3 formed a typical donor (D)-acceptor (A) structure, which led to the red-shifted absorption and fluorescence spectrum. The synthesized BODIPY exhibited intense green emission, with fluorescence quantum yield of 0.66, 0.29, and 0.19 for BDP-1, BDP-2 and BDP-3 respectively. The decrease in fluorescence of BDP-2 and BDP-3 was probably ascribed to the enhanced intramolecular charge transfer because of the introduction of the NI group. The good biocompatibility and low cytotoxicity of the synthesized BODIPY compounds were verified by the CCK-8 assay. The subcellular localization of the three compounds was further evaluated through a confocal laser scanning microscope. The results showed that these BODIPY derivatives were mainly localized in the lysosomes of cancer cells. Thus, the synthesized BODIPY fluorescent dyes show promising applications in tumor imaging benefiting from their good biocompatibility and strong fluorescence.

  DOI：

  10.1142/s1088424624500391

文献信息

• Bodipy dyes bearing oligo(ethylene glycol) groups on the meso-phenyl ring: tuneable solid-state photoluminescence and highly efficient OLEDs
  作者：Cui-Lian Liu、Yong Chen、Deepak P. Shelar、Cong Li、Gang Cheng、Wen-Fu Fu

  DOI：10.1039/c4tc00720d

  日期：——

  Borondipyrromethene (Bodipy) dyes with strong solid-state photoluminescence are highly desirable for their applications in OLEDs. In this work, a series of meso-(4-R–C6H4)-substituted Bodipy dyes (R = H for B1; R = (OCH2CH2)nOCH2CH3, n = 0–3 for B2–B5, respectively) were prepared through an acid-catalyzed reaction. The flexible ether groups attached to the periphery of B2–B5 are expected to influence

  具有强固态光致发光的硼二吡咯亚甲基（Bodipy）染料对于其在OLED中的应用是非常需要的。在这项工作中，一系列内消旋-（4-R–C 6 H 4）取代的Bodipy染料（B1的R = H ； R =（OCH 2 CH 2）n OCH 2 CH 3，n = 0–3 B2-B5分别）是通过酸催化反应制备的。预计连接在B2-B5外围的柔性醚基会影响固态的分子排列和分子间的相互作用。B1-B4的晶体学分析揭示了内消旋-苯环几乎与茚并平面正交。在B1中观察到分子间π–π相互作用，但在B2–B4中不存在。因此，染料B1在固态时微弱发射，而B2-B4在红色区域中发射强，发射量子产率高达0.33。掺有B2的PMMA膜示两个分离的发射峰，并且它们的相对强度取决于浓度，随着浓度从5 wt％逐渐增加到80 wt％，导致荧光颜色从绿黄色变为红色。发现在基态下形成二聚体是造成在凝聚态下红色发射的原因。有效的OLED