4-[2-(3,4-dicyanophenyl)ethynyl]benzaldehyde | 254902-82-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-[2-(3,4-dicyanophenyl)ethynyl]benzaldehyde
• 英文别名: 4-[2-(4-Formylphenyl)ethynyl]benzene-1,2-dicarbonitrile
• CAS: 254902-82-4
• 化学式: C₁₇H₈N₂O
• 分子量: 256.263
• InChiKey: LAWZNRGLDJUEEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  lanthanide(III)chloride heptahydrate 、 4-[2-(3,4-dicyanophenyl)ethynyl]benzaldehyde 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 戊醇 、 N,N-二甲基乙酰胺 为溶剂， 以54 %的产率得到
  参考文献：
  名称：

  Tetra (C60) 镧酞菁：三阶非线性光学特性的设计、合成和研究

  摘要：

  构建具有有效光诱导分子内电子转移 (PET) 和能量转移 (ET) 过程的分子对于增强非线性光学 (NLO) 特性至关重要。从分子设计的角度构建了一种新型D-π-A型化合物，即四(C 60 )-LaPc，其中以四甲酰基酞菁为供体，四个C 60为受体，并引入苯乙炔基团。作为π电子桥，可以增加分子共轭，降低空间位点电阻，扩大分子的共面性，从而使分子内电荷转移更容易。Tetra (C 60 )–LaPc 具有出色的 NLO 特性，具有巨大的非线性吸收系数（45 cm GW-1和大的三阶磁化率（4.05 × 10 -10 esu），优于LaPc 和C 60。与单组分相比，除了在 532 nm 处表现出优异的非线性光学响应外，四 (C 60 )–LaPc 还将限制范围扩大到近红外区域，在 1064 nm 处显示出光学非线性的显着增强。这可以归因于 C 60和 LaPc之间不同的非线性吸收机制和有效的

  DOI：

  10.1039/d2cp02472a
• 作为产物：
  描述：

  4-碘酞腈 、 4-乙炔基苯甲醛 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以70 %的产率得到4-[2-(3,4-dicyanophenyl)ethynyl]benzaldehyde
  参考文献：
  名称：

  Tetra (C60) 镧酞菁：三阶非线性光学特性的设计、合成和研究

  摘要：

  构建具有有效光诱导分子内电子转移 (PET) 和能量转移 (ET) 过程的分子对于增强非线性光学 (NLO) 特性至关重要。从分子设计的角度构建了一种新型D-π-A型化合物，即四(C 60 )-LaPc，其中以四甲酰基酞菁为供体，四个C 60为受体，并引入苯乙炔基团。作为π电子桥，可以增加分子共轭，降低空间位点电阻，扩大分子的共面性，从而使分子内电荷转移更容易。Tetra (C 60 )–LaPc 具有出色的 NLO 特性，具有巨大的非线性吸收系数（45 cm GW-1和大的三阶磁化率（4.05 × 10 -10 esu），优于LaPc 和C 60。与单组分相比，除了在 532 nm 处表现出优异的非线性光学响应外，四 (C 60 )–LaPc 还将限制范围扩大到近红外区域，在 1064 nm 处显示出光学非线性的显着增强。这可以归因于 C 60和 LaPc之间不同的非线性吸收机制和有效的

  DOI：

  10.1039/d2cp02472a

文献信息

• <i>gem</i>-Dibromovinyl phthalonitriles: synthesis, structure elucidation, Hirshfeld surface analysis and energy framework calculations
  作者：Hasrat Ali、Johan E. van Lier

  DOI：10.1039/d3nj04853e

  日期：2024.4.2

  assigned structures were further supported by X-ray crystallographic techniques. The crystal structures showed primarily C–H⋯N, C–H⋯Br, C–Br⋯N and π⋯π interactions. The overall intermolecular interactions in the structures were quantified and fully described by Hirshfeld surface analysis. In addition, energy-frame calculations were used to analyse the three-dimensional topology of the crystal packing

  合成了一系列由偕二溴乙烯基邻苯二甲腈衍生物组成的多功能酞菁前体，并通过各种光谱技术对其进行了表征。X 射线晶体学技术进一步支持了指定的结构。晶体结构主要显示C-H⋯N、C-H⋯Br、C-Br⋯N和π⋯π相互作用。通过赫什菲尔德表面分析对结构中的整体分子间相互作用进行了量化和充分描述。此外，能量框架计算用于分析晶体堆积的三维拓扑。所有化合物的色散能框架均优于静电框架。
• Synthesis and Properties of Star-Shaped Multiporphyrin−Phthalocyanine Light-Harvesting Arrays
  作者：Junzhong Li、James R. Diers、Jyoti Seth、Sung Ik Yang、David F. Bocian、Dewey Holten、Jonathan S. Lindsey

  DOI：10.1021/jo991001g

  日期：1999.12.1

  Light-harvesting arrays containing four porphyrins covalently linked to a phthalocyanine in a starshaped architecture have been synthesized. Cyclotetramerization of an ethyne-linked porphyrin-phthalonitrile in l-pentanol in the presence of MgCl2 and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) afforded the all-magnesium porphyrin-phthalocyanine pentad in 45% yield. Similar reaction using Zn(OAc)(2). 2H(2)O afforded the all-zinc porphyrin-phthalocyanine pentad in 15% yield. Arrays with different metals (free base, Mg, Zn) in the porphyrin and phthalocyanine macrocycles have been prepared by selective demetalation and metalation steps. This approach provides rapid and convergent access to multiporphyrin-phthalocyanine arrays in diverse metalation states. The arrays are reasonably soluble in organic solvents such as toluene, THF, and CH2Cl2. The arrays exhibit strong absorption in the blue and red regions. Time-resolved and static optical measurements indicate that intramolecular singlet-excited-state energy transfer from the porphyrin to the phthalocyanine moiety is extremely rapid (picoseconds) and efficient. Ground-state electronic communication among the porphyrins is indicated by rapid hole/electron hopping among the metalloporphyrins in the arrays as detected by EPR measurements on the singly oxidized pentads. These physical measurements indicate that the porphyrin-phthalocyanine pentads possess favorable characteristics for light harvesting and other photonics applications.
• Efficient Synthesis of Light-Harvesting Arrays Composed of Eight Porphyrins and One Phthalocyanine
  作者：Junzhong Li、Jonathan S. Lindsey

  DOI：10.1021/jo991102e

  日期：1999.12.1

  Effective light-harvesting arrays require multiple photoactive:energy donors that funnel energy to an energy acceptor. Porphyrins and phthalocyanines are attractive components for light-harvesting arrays due to their strong absorption in the blue and red regions, respectively, and because energy transfer can occur from porphyrin to phthalocyanine regardless of their respective metalation states. Star-shaped light-harvesting arrays comprised of eight peripheral porphyrins and one core phthalocyanine have been prepared by a streamlined synthesis involving minimal reliance on protecting groups, a high degree of convergence, and facile chromatographic purification. The synthesis involves three distinct stages of complementary chemistries (porphyrin formation, Pd-mediated porphyrin dimer formation, phthalocyanine formation). Statistical reaction of p-iodobenzaldehyde, a phthalonitrile-linked benzaldehyde, and 5-mesityldipyrromethane afforded the desired trans-iodo/phthalonitrile-substituted porphyrin, which underwent Pd-mediated coupling with a monoethynyl porphyrin to give the porphyrin dimer bearing a phthalonitrile unit. Reaction of the dimer in 1-pentanol in the presence of MgCl2 and DBU for 48 h at 145 degrees C afforded the all-magnesium (porphyrin)(8)-phthalocyanine nonamer (MgP)(8)MgPc in 5.0% yield. The same reaction with lithium pentoxide in 1-pentanol for 2 h at 145 OC gave the all-free base nonamer (H2P)(8)H(2)Pe in 34% yield. The all-zinc nonamer (ZnP)(8)ZnPc was prepared by addition of zinc acetate at the end of the reaction. Similar treatment of a monomeric porphyrin-phthalonitrile afforded the pentameric (ZnP)(4)ZnPc in 58% yield. The (MgP)(8)MgPe was also obtained by magnesium insertion of(H2P)(8)H2Pc; The three nonamers were readily purified and are soluble in solvents such as toluene, THF, and CH2Cl2. Each nonamer absorbs strongly across the solar spectrum and exhibits efficient energy transfer from the porphyrins to the phthalocyanine.
• Tetra (C₆₀) lanthanum phthalocyanine: design, synthesis and investigation of the third-order nonlinear optical properties
  作者：Min Zhu、Jiale Ding、Sen Niu、Yunhe Zhang、Guibin Wang

  DOI：10.1039/d2cp02472a

  日期：——

  intramolecular electron transfer (PET) and energy transfer (ET) processes is critical for the enhancement of the nonlinear optical (NLO) properties. A novel D–π–A type compound, namely tetra (C60)–LaPc, has been constructed from a molecular design perspective, wherein tetra-formyl phthalocyanine is used as a donor, four C60 as acceptors and the phenylacetylene group is introduced into it as π-electron bridge

  构建具有有效光诱导分子内电子转移 (PET) 和能量转移 (ET) 过程的分子对于增强非线性光学 (NLO) 特性至关重要。从分子设计的角度构建了一种新型D-π-A型化合物，即四(C 60 )-LaPc，其中以四甲酰基酞菁为供体，四个C 60为受体，并引入苯乙炔基团。作为π电子桥，可以增加分子共轭，降低空间位点电阻，扩大分子的共面性，从而使分子内电荷转移更容易。Tetra (C 60 )–LaPc 具有出色的 NLO 特性，具有巨大的非线性吸收系数（45 cm GW-1和大的三阶磁化率（4.05 × 10 -10 esu），优于LaPc 和C 60。与单组分相比，除了在 532 nm 处表现出优异的非线性光学响应外，四 (C 60 )–LaPc 还将限制范围扩大到近红外区域，在 1064 nm 处显示出光学非线性的显着增强。这可以归因于 C 60和 LaPc之间不同的非线性吸收机制和有效的