Ni(II)-2-vinyl-5,10,15,20-tetraphenylporphyrin | 42565-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: Ni(II)-2-vinyl-5,10,15,20-tetraphenylporphyrin
• CAS: 42565-86-6
• 化学式: C₄₆H₃₀N₄Ni
• 分子量: 697.461
• InChiKey: TWJKWGGGZXZTMT-WNTUHYLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.14
• 重原子数：
  51.0
• 可旋转键数：
  5.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.98
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Ni(II)-2-vinyl-5,10,15,20-tetraphenylporphyrin 在 三氟乙酸 作用下， 以 氯仿 、 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Studies on selective β/β′ bromination of π-extended porphyrins and subsequent coupling reactions

  摘要：

  研究发现，β、β′-π-扩展卟啉的单溴化反应选择性地发生在卟啉的 β 或 β′位置，即与融合芳香环相对的位置。随后对生成的溴卟啉进行 Sonogashira 或 Heck 偶联，在 π-扩展的卟啉上引入羧基苯乙炔基或丙烯酸基。为 Sonogashira 和 Heck 偶联反应找到了最佳反应条件。与 π-扩展卟啉起始材料和原始未修饰卟啉相比，所有偶联产物在紫外-可见吸收光谱中的索雷特带和 Q 带都出现了拓宽和红移。

  DOI：

  10.1007/s11164-013-1048-9

文献信息

• Diels-Alder Reaction of Ni(II) β-Vinyl-<i>meso</i>-tetraphenylporphyrin; A General Method for Synthesis of Functionalized Porphyrins
  作者：Kiyoshi Matsumoto、Shinya Kimura、Takuya Morishita、Yukihiro Misumi、Naoto Hayashi

  DOI：10.1055/s-2000-6506

  日期：2000.2

  Ni(II)β-Vinyl-meso-tetraphenylporphyrin underwent Diels-Alder reaction with a variety of dienophiles to give the corresponding porphyrins via 1,3-hydrogen shift of the initial adducts in good to moderate yields.

  Ni(II)β-乙烯基-中间体四苯基卟啉与多种二烯亲电试剂发生Diels-Alder反应，经过初始加成物的1,3-氢转移，获得相应的卟啉，产率良好至适中。
• Novel pyrazoline and pyrazole porphyrin derivatives: synthesis and photophysical properties
  作者：Nuno M.M. Moura、Maria A.F. Faustino、Maria G.P.M.S. Neves、Augusto C. Tomé、El Mostapha Rakib、Abdellah Hannioui、Souad Mojahidi、Steffen Hackbarth、Beate Röder、Filipe A. Almeida Paz、Artur M.S. Silva、José A.S. Cavaleiro

  DOI：10.1016/j.tet.2012.07.072

  日期：2012.9

  pyrazoline derivatives with DDQ affords the corresponding pyrazole derivatives with moderate to excellent yields. When the hydrolysis of ester group in the pyrazoline derivatives was considered, it was observed the concomitant oxidation of the heterocyclic unit, which allowed directly obtaining porphyrin-pyrazole derivatives with a carboxylic group, in very good yields. The photophysical properties of the

  2 -乙烯基- 5,10,15,20- - tetraphenylporphyrinatozinc（II）发生反应以腈亚胺，从乙基肼基α-bromoglyoxylates原位生成，从而提供良好的对应的吡唑啉以优良的产率。用DDQ处理吡唑啉衍生物可得到相应的吡唑衍生物，产率中等至优异。当考虑吡唑啉衍生物中酯基的水解时，观察到杂环单元的伴随氧化，这允许以非常好的收率直接获得具有羧基的卟啉-吡唑衍生物。 吡唑啉和吡唑卟啉衍生物的光物理性质表明，杂环取代基的影响受到这些分子聚集趋势的限制。所有其他特性，尤其是三重态动力学均不受影响。具有低聚集趋势的加合物显示出非常高的单线态氧产率，这使得这些化合物作为用作PDT的光敏剂而引起人们的兴趣。
• Synthesis of β,β′-edge fused, π-extended porphyrins and their applications in the dye-sensitized solar cells
  作者：Jiaying Yan、Yaqing Feng、Xiao Peng、Yuanchao Li、Nuonuo Zhang、Xianggao Li、Bao Zhang

  DOI：10.1016/j.tetlet.2013.10.132

  日期：2013.12

  Four it-extended, beta,beta' aromatic ring fused porphyrins including mono- and opp-dibenzoporphyrins bearing two carboxyl groups at only one fused benzo group were synthesized. The optical results by UV-vis spectroscopy indicate that when compared with the absorption spectra of monobenzoporphyrins, greater light-harvesting capabilities can be realized for opp-dibenzoporphyrins with two benzo group at the opposite beta,beta' positions of the porphyrin. The photovoltaic properties of these pi-extended porphyrins were examined for the first time and the highest conversion efficiency of 1.62% was realized for opp-dibenzoporphyrin 8a-sensitized solar cell, which is similar to 60% higher than that of monobenzoporphyrin 4a based solar cell indicating the effect of an extra aromatic pi conjugation on the light-harvesting capabilities of pi-extended porphyrins. Subsequent DFT calculation results supported our results obtained in the optical and photovoltaic studies. (C) 2013 Elsevier Ltd. All rights reserved.