4,4-difluoro-8-[3,4-bis(3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethoxymethyl)propoxy]phenyl-1,3,5,7-tetramethyl-2,6-diethynyl-4-bora-3a,4a-diaza-s-indacene | 1259292-38-0

• 英文名称: 4,4-difluoro-8-[3,4-bis(3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethoxymethyl)propoxy]phenyl-1,3,5,7-tetramethyl-2,6-diethynyl-4-bora-3a,4a-diaza-s-indacene
• CAS: 1259292-38-0
• 化学式: C₅₉H₉₁BF₂N₂O₁₈
• 分子量: 1165.18
• InChiKey: CACFGWUNQSDZCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  甲醇 、 4,4-difluoro-8-[3,4-bis(3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethoxymethyl)propoxy]phenyl-1,3,5,7-tetramethyl-2,6-diethynyl-4-bora-3a,4a-diaza-s-indacene 在 sodium methylate 作用下， 以52%的产率得到4,4-dimethoxy-8-[3,4-bis(3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxymethyl}propoxy)phenyl]-1,3,5,7-tetramethyl-2,6-diethynyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Highly Water-Soluble Neutral BODIPY Dyes with Controllable Fluorescence Quantum Yields

  摘要：

  A series of novel highly water-soluble neutral BODIPY dyes have been obtained by functionalization of BODIPY dyes with branched oligo(ethylene glycol)methyl ether groups at positions 8, 2 and 6 or 4 and 4'. Use of an ortho-substituent group of branched oligo(ethylene glycol)methyl ether on the meso-phenyl ring of BODIPY dyes and replacement of the fluorine atoms of BODIPY dyes at positions 4 and 4' with methyloxy or ethynyl subunits significantly enhance fluorescence quantum yields of BODIPY dyes.

  DOI：

  10.1021/ol102758z
• 作为产物：
  描述：

  三甘醇单甲醚 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三氟化硼乙醚 、 碘 、 三溴化磷 、 碘酸 、 sodium hydride 、 potassium carbonate 、 sodium fluoride 、 N,N-二异丙基乙胺 、 9-硼双环[3.3.1]壬烷 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 27.91h， 生成 4,4-difluoro-8-[3,4-bis(3-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}-2-{2-[2-(2-methoxyethoxy)ethoxy]ethoxy}ethoxymethyl)propoxy]phenyl-1,3,5,7-tetramethyl-2,6-diethynyl-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Highly Water-Soluble Neutral BODIPY Dyes with Controllable Fluorescence Quantum Yields

  摘要：

  A series of novel highly water-soluble neutral BODIPY dyes have been obtained by functionalization of BODIPY dyes with branched oligo(ethylene glycol)methyl ether groups at positions 8, 2 and 6 or 4 and 4'. Use of an ortho-substituent group of branched oligo(ethylene glycol)methyl ether on the meso-phenyl ring of BODIPY dyes and replacement of the fluorine atoms of BODIPY dyes at positions 4 and 4' with methyloxy or ethynyl subunits significantly enhance fluorescence quantum yields of BODIPY dyes.

  DOI：

  10.1021/ol102758z

文献信息

• Highly water-soluble neutral near-infrared emissive BODIPY polymeric dyes
  作者：Shilei Zhu、Nethaniah Dorh、Jingtuo Zhang、Giri Vegesna、Haihua Li、Fen-Tair Luo、Ashutosh Tiwari、Haiying Liu

  DOI：10.1039/c2jm14920f

  日期：——

  Three highly water-soluble near-infrared emissive polymeric BODIPY dyes (polymers A–C) were prepared by the palladium-catalyzed Suzuki polymerization of highly water-soluble 2,6-diiodo-3,5-distyryl-BODIPY dyes with 1,4-phenyldiboronic acid and 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9,9-di[1-[2-(2-methoxyethoxy)ethoxy]ethyl]fluorene, respectively. Partial replacement of fluorine subunits of BODIPY cores at 4,4-positions of polymer C with ethynyl subunits resulted in a highly water-soluble BODIPY polymeric dye (polymer D). Polymers A–D show solubility of at least 20 mg mL−1 in aqueous solution. For comparison purposes, polymers E and F were prepared by palladium-catalyzed Sonogashira polymerization of highly water-soluble 2,6-diiodo-3,5-distyryl-BODIPY dye with highly water-soluble 1,4-diethynylbenzene and 2,6-diethynyl BODIPY dye bearing branched oligo(ethylene glycol)methyl ether residues, respectively. Upon comparison, polymer E shows low solubility in aqueous solution (0.1 mg mL−1), whereas polymer F is almost insoluble in aqueous solution (less than 0.05 mg mL−1), but both are soluble in organic solvents such as chloroform, DMSO and DMF (at least 10 mg mL−1).

  制备了三种高水溶性近红外发光聚合BODIPY染料（聚合物A-C），通过钯催化的铃木聚合反应将高水溶性的2,6-二碘-3,5-二苯乙烯-BODIPY染料与1,4-苯二硼酸和2,7-双（4,4,5,5-四甲基-1,3,2-二氧烷硼烷-2-基)-9,9-二[1-[2-(2-甲氧基乙氧)乙氧]乙基]荧光烯进行聚合反应。部分将聚合物C的BODIPY核心在4,4位的氟单元替换为乙炔单元，得到了高度水溶性的BODIPY聚合物染料（聚合物D）。聚合物A-D在水相中的溶解度至少为20 mg mL−1。作为比较，聚合物E和F是通过钯催化的Sonogashira聚合，将高水溶性的2,6-二碘-3,5-二苯乙烯-BODIPY染料与高水溶性1,4-二乙炔苯和带有支链聚乙ylene glycol甲基醚残基的2,6-二乙炔BODIPY染料聚合而成的。在比较中，聚合物E在水相中的溶解度较低（0.1 mg mL−1），而聚合物F几乎不溶于水相（小于0.05 mg mL−1），但两者在有机溶剂如氯仿、DMSO和DMF中均可溶解（至少10 mg mL−1）。