3,5-diformyl-8-(4-bromophenyl)-4-bora-3a,4a-diaza-s-indacene | 1299466-64-0

• 英文名称: 3,5-diformyl-8-(4-bromophenyl)-4-bora-3a,4a-diaza-s-indacene
• CAS: 1299466-64-0
• 化学式: C₁₇H₁₀BBrF₂N₂O₂
• 分子量: 402.99
• InChiKey: GEGKYIPUGLZMBO-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：

  吡咯 、 3,5-diformyl-8-(4-bromophenyl)-4-bora-3a,4a-diaza-s-indacene 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到3,5-bis(dipyrromethanyl)-8-(4-bromophenyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  3,5-双（双吡咯烷甲酰基）硼-双吡咯烷酮的合成，光谱，电化学和阴离子结合性能

  摘要：

  含有3,5-位取代基dipyrromethanyl，双（3,5- dipyrromethanyl）BODIPYs四个新的硼dipyrromethenes（BODIPYs）5 - 8，分别通过处理其相应的3,5-二甲酰基BODIPYs合成1 - 4与过量的吡咯下温和酸催化的反应条件。化合物5 – 8稳定，可自由溶于常见的有机溶剂。使用一维，二维NMR，高分辨率质谱（HRMS），吸收，荧光和电化学技术来表征化合物。光谱和电化学研究表明，与相同位置的甲酰基相比，BODIPY的3,5-位的亚吡咯烷甲基具有更少的电子缺陷。的阴离子结合研究表明，双（3,5- dipyrromethanyl）BODIPY化合物含有四个吡咯NH组显示优先与F结合-离子比其它阴离子，通过使用NMR，荧光和电化学研究证实。

  DOI：

  10.1021/ic202758r
• 作为产物：
  描述：

  5-(4-bromophenyl)-1,9-diformyldipyrrylmethane 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以9%的产率得到3,5-diformyl-8-(4-bromophenyl)-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  3,5-Diformylboron Dipyrromethenes as Fluorescent pH Sensors

  摘要：

  A series of boron dipyrromethene (BODIPY) dyes containing two aldehyde functional groups at the 3 and 5 positions have been synthesized in low-to-decent yields in two steps. In the first step, the meso-aryl dipyrromethanes were treated with POCl(3) in N,N-dimethylformamide to afford 1,9-diformylated dipyrromethanes. In the second step, the diformylated dipyrromethanes were first in situ oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and then reacted with BF(3)center dot OEt(2) to afford 3,5-diformylboron dipyrromethenes. The X-ray structural analysis indicated that the aldehyde groups are involved in intramolecular hydrogen bonding with fluoride atoms, which may be responsible for the stability of the diformylated BODIPY compounds. The presence of two formyl groups significantly alters the electronic properties, which is clearly evident in downfield shifts in the (1)H and (19)F NMR spectra, bathochromic shifts in the absorption and fluorescence spectra, better quantum yields, and increased lifetimes compared to 3,5-unsubstituted BODIPYs. Furthermore, 3,5-diformylboron dipyrromethenes are highly electron-deficient and undergo facile reductions compared to unsubstituted BODIPYs. These compounds exhibit pH-dependent on/off fluorescence and thus act as fluorescent pH sensors.

  DOI：

  10.1021/ic102499h