8-(4-(ferrocene-1-yl ethynyl)phenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene | 1222084-12-9

• 英文名称: 8-(4-(ferrocene-1-yl ethynyl)phenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 4,4-difluoro-8-[4-(ferrocenylethynyl)phenyl]-4-bora-3a,4a-diaza-s-indacene
• CAS: 1222084-12-9
• 化学式: C₂₇H₁₉BF₂FeN₂
• 分子量: 476.116
• InChiKey: NLBDSXPRZAKIGY-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

• 作为产物：
  描述：

  二茂铁乙炔 、 4,4-difluoro-8-(4-iodophenyl)-4-bora-3a,4a-diaza-s-indacene 在 Et₃N 、 catalyst:CuI/Pd(PPh₃)2Cl₂ 作用下， 以 甲苯 为溶剂， 以65%的产率得到8-(4-(ferrocene-1-yl ethynyl)phenyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Synthesis of boron-dipyrromethene–ferrocene conjugates

  摘要：

  Synthesis, spectral, electrochemical and photophysical properties of four BODIPY-ferrocene conjugates in which one or two ferrocenyl groups were covalently connected either directly to boron-dipyrromethene framework or to meso-phenyl group of boron-dipyrromethene unit are described. The BODIPY-ferrocene conjugates were prepared by adopting different synthetic routes. The absorption studies indicated the presence of charge transfer band in BODIPY-ferrocene conjugates in which the ferrocenyl group(s) were directly connected to boron-dipyrromethene framework. The electrochemical studies on conjugates indicated that ferrocenyl group was difficult to oxidize whereas boron-dipyrromethene unit was easier to reduce. The conjugates were non-fluorescent due to electron transfer from ferrocene to boron-dipyrromethene unit. However, when ferrocene was oxidized to ferrocenium ion with an oxidizing agent, the conjugates exhibited fluorescence with decent quantum yields (0.17-0.31) and lifetimes (3.8-5.2 ns). (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2010.01.009

文献信息

• Second-order nonlinear polarizability of ferrocene–BODIPY donor–acceptor adducts. Quantifying charge redistribution in the excited state
  作者：Navdeep Kaur、Nick Van Steerteghem、Priya Singla、Paramjit Kaur、Koen Clays、Kamaljit Singh

  DOI：10.1039/c6dt04455g

  日期：——

  4-benzoquinone (DDQ), the latter two sets (imine and alkyne linked) of dyads were obtained through Schiff base condensation or Sonogashira coupling reactions, respectively. The compounds were fully characterized with spectroscopic data and single crystal X-ray analysis in one case. The peaks corresponding to the Fe(II)/Fe(III) redox couple at 0.33 to 0.38 V showed a varying degree of positive anodic shift

  一系列成对层，并使用二茂铁（Fc）的作为供体和4,4-二氟-4-硼-3a，4a-二氮杂-三单元组的小号-indacene（BODIPY）作为受体，连接直接地或者通过一个ñ -phenylmethanimine已经合成了乙炔基或乙炔基接头。前者（直接连接的）二元化合物是通过吡咯与二茂铁羧甲醛或1,1'-二茂铁甲醛的酸催化缩合反应，然后用2,3-二氯-5,6-二氰基-1,4-苯醌（DDQ）氧化制备的，后两组（亚胺和炔烃连接的）二元组分别通过席夫碱缩合或Sonogashira偶联反应获得。在一种情况下，利用光谱数据和单晶X射线分析对化合物进行了全面表征。对应于Fe（II）/ Fe（III）的氧化还原对在0.33至0.38 V时显示出不同程度的正阳极移位，这反映了相应的BODIPY单元的强电子吸收效应。使用飞秒超瑞利散射（HRS）方法在1300 nm下于氯仿中测量第一个超极化能力β。有趣的是，从β