8-(phenethynyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene | 1414345-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 8-(phenethynyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
• 英文别名: 8-(2-phenylethynyl)BODIPY；2,2-Difluoro-8-(2-phenylethynyl)-1lambda5,3-diaza-2-boratricyclo[7.3.0.0,3,7]dodeca-1(12),4,6,8,10-pentaen-1-ylium-2-uide；2,2-difluoro-8-(2-phenylethynyl)-3-aza-1-azonia-2-boranuidatricyclo[7.3.0.03,7]dodeca-1(12),4,6,8,10-pentaene
• CAS: 1414345-91-7
• 化学式: C₁₇H₁₁BF₂N₂
• 分子量: 292.096
• InChiKey: FHHNYZCIKRBVJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  7.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二-1H-吡咯-1-基甲酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 5.58h， 生成 8-(phenethynyl)-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  参考文献：
  名称：

  Synthesis of Meso-Halogenated BODIPYs and Access to Meso-Substituted Analogues

  摘要：

  8-Halogenated boradiaza-s-indacenes can be efficiently prepared from dipyrrylketones. The new dyes react smoothly with nucleophiles to yield N-, O-, and S-substituted chromophores, as well as transition-metal-catalyzed cross-coupling reactions. The nature of the new substitutent has a strong influence on the spectral properties of the dyes.

  DOI：

  10.1021/ol3028225

文献信息

• Meso enyne substituted BODIPYs: synthesis, structure and properties
  作者：Bhausaheb Dhokale、Thaksen Jadhav、Shaikh M. Mobin、Rajneesh Misra

  DOI：10.1039/c5dt00565e

  日期：——

  results in meso enyne substituted BODIPYs with different substituents. The meso enyne substituted BODIPYs show blue shifted absorption and red shifted emission with large Stokes shift compared to meso alkynylated BODIPYs. The single crystal structures of BODIPYs 2a, 3b, 4a and 2d are reported. Their packing diagram exhibits extensive intermolecular C–H⋯π, C–H⋯F hydrogen bonding and π⋯π stacking interactions

  我们报告的合成内消旋由8-氯BODIPY与Sonogashira偶联条件下，末端炔烃反应的烯炔取代的BODIPYs，并加入Pd-Cu系催化末端炔烃的反应hydroalkynylation，横跨-C的C-键内消旋炔基化BODIPYs。通过使不同的内消旋炔基化的BODIPY与各种末端炔烃反应来探索反应的范围，这导致内消旋的炔烃取代的BODIPYs具有不同的取代基。与内消旋炔基化的BODIPYs相比，内消旋烯炔取代的BODIPYs显示蓝移吸收和红移发射，斯托克斯位移大。BODIPYs 2a的单晶结构，图3b，图4a和2d中被报告。它们的堆积图显示出广泛的分子间C–H⋯π，C–H⋯F氢键和π⋯π堆积相互作用，从而导致一维超分子框架扩展为复杂的3D结构框架。
• <i>Meso</i> Alkynylated Tetraphenylethylene (TPE) and 2,3,3-Triphenylacrylonitrile (TPAN) Substituted BODIPYs
  作者：Bhausaheb Dhokale、Thaksen Jadhav、Shaikh M. Mobin、Rajneesh Misra

  DOI：10.1021/acs.joc.5b01117

  日期：2015.8.21

  The tetraphenylethylene (TPE) substituted BODIPY 2a, and 2,3,3-triphenylacrylonitrile (TPAN) substituted BODIPYs 2b and 2c were designed and synthesized by the Pd-catalyzed Sonogagaira cross-coupling reaction. Their photophysical and electrochemical properties were investigated. The BODIPY 2a exhibits strong D-A interaction with poor fluorescence quantum yield. The BODIPYs 2b and 2c show red-shifted absorption and emission with higher fluorescence quantum yield compared to BODIPY 2a. The photonic properties of BODIPYs 2a-2c were compared with 4-ethynylbenzonitrile substituted BODIPY 3 and phenylacetylene substituted BODIPY 4. The results reveal that the electron donating group at the meso position of BODIPY blue shifts the absorption and emission with decreased fluorescence quantum yield, whereas the electron withdrawing group at the meso position of BODIPY red shifts the absorption and emission with enhanced quantum yields. The single crystal structures of BODIPYs 2a and 2b reflect the planar orientation of meso substituent and the BODIPY core, which leads to close pi-pi stacking. The extensive pi-pi stacking and strong donor acceptor (D-A) interaction makes these BODIPYs ALE inactive. The experimental observations were supported by DFT calculation.